Vernakalant hydrochloride, RSD-1235, -Drug Synthesis Database

【结构式】

【药物名称】Vernakalant hydrochloride, RSD-1235

【化学名称】1-[(1R,2R)-2-[2-(3,4-Dimethoxyphenyl)ethoxy]cyclohexyl]pyrrolidin-(3R)-ol hydrochloride

【CA登记号】748810-28-8, 794466-70-9 (free base)

【分子式】C₂₀H₃₂ClNO₄

【分子量】385.9251

【开发单位】Cardiome Pharma Corp. (CA); co-developed with Astellas Pharma US, Inc. (US).

【药理作用】Antiarrhythmic drug, Dual sodium/potassium channel blocker

合成路线1 合成路线2 合成路线3 合成路线4 合成路线5

合成路线1

Condensation of (1S,2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexyl tosylate (I) with 3(R)-benzyloxypyrrolidine (II) provides vernakalant benzyl ether (III), which is then debenzylated by catalytic hydrogenolysis over Pd/C (1). In a more direct approach, tosylate (I) is condensed with 3(R)-hydroxypyrrolidine (IV) to provide vernakalant (1, 2). An alternative strategy consists of the cyclization of (1R,2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexylamine (V) with (R )-2-acetoxysuccinic anhydride (VI) by means of acetyl chloride or with ethyl 4-chloro-3(R )-hydroxybutyrate (VII) to give, respectively, the cyclic imide (VIIIa) or the pyrrolidinone (VIIIb), which is subsequently reduced and deprotected by means of Red-Al to yield the title hydroxypyrrolidine derivative (2). The O-benzyl precursor of vernakalant (III) can alternatively be obtained by condensation of 2(R )-[3(R )-benzyloxy-1-pyrrolidinyl]cyclohexan-1(R )-ol (IX) with 3,4-dimethoxyphenethyl trichloroacetimidate (X) (prepared from dimethoxyphenethyl alcohol [XI] and trichloroacetonitrile) in the presence of trifluoromethanesulfonic acid (2, 3). A related strategy for preparing the succinimide precursor of vernakalant (VIIIa) consists of the condensation of 2(R)-acetoxy-N-[2(R)-hydroxy-1(R)-cyclohexyl]succinimide (XII) with imidate (X) in the presence of boron trifluoride etherate (4). Scheme 1.

参考文献中间体

【1】 Beatch, G.N., Choi, L.S.L., Jung, G. et al. (Cardiome Pharma Corp.). Aminocyclohexyl ether compounds and uses thereof. EP 1560812, EP1666459, JP 2006525227, WO 2004099137.
【2】 Plouvier, B.M.C., Chou, D.T.H., Jung, G. et al. (Cardiome Pharma Corp.). Synthetic process for aminocyclohexyl ether compounds. WO 2006088525.
【3】 Machiya, K., Ike, K., Watanabe, M., Yoshino, T., Okamoto, T., Morinaga, Y., Mizobata, S. (Astellas Pharma, Inc.). Production method of optically active cyclohexane ether compounds. WO 2006075778.
【4】 Roth, C.J., Jung, G., Plouvier, B.M.C., Chou, D.T.H., Yee, J.G.K. (Cardiome Pharma Corp.). Synthetic processes for the preparation of aminocyclohexyl ether compounds. WO 2006138673.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(VIIIa)	65269			C₂₂H₂₉NO₇	详情	详情
(VIIIb)	65270			C₂₀H₂₉NO₅	详情	详情
(I)	65263	(1S,2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexyl tosylate		C₂₃H₃₀O₆S	详情	详情
(II)	65264	(3R)-benzyloxypyrrolidine		C₁₁H₁₅NO	详情	详情
(III)	65265	vernakalant benzyl ether		C₂₇H₃₇NO₄	详情	详情
(IV)	14490	(3R)tetrahydro-1H-pyrrol-3-ol; R-3-hydroxypyrrolidine	2799-21-5	C₄H₉NO	详情	详情
(V)	65266	(1R,2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexylamine		C₁₆H₂₅NO₃	详情	详情
(VI)	65267	(2R)-acetoxysuccinic anhydride	79814-40-7	C₆H₆O₅	详情	详情
(VII)	65268	ethyl 4-chloro-(3R)-hydroxybutyrate;	90866-33-4	C₆H₁₁ClO₃	详情	详情
(IX)	65271	(2R)-[(3R)-benzyloxy-1-pyrrolidinyl]cyclohexan-(1R)-ol		C₁₆H₂₅NO₂	详情	详情
(X)	65272	3,4-dimethoxyphenethyl trichloroacetimidate		C₁₂H₁₄Cl₃NO₃	详情	详情
(XI)	38711	2-(3,4-dimethoxyphenyl)-1-ethanol	7417-21-2	C₁₀H₁₄O₃	详情	详情
(XII)	65273	(2R)-acetoxy-N-[(2R)-hydroxy-(1R)-cyclohexyl]succinimide		C₁₂H₁₇O₅	详情	详情

合成路线2

The tosylate precursor (I) can be prepared by a number of different methods. Microbial dihydroxylation of chlorobenzene (XIII) gives (1S,2S)-3-chlorocyclohexa-3,5-diene-1,2-diol (XIV), which is further hydrogenated to (XV) in the presence of Rh/Al 2O3. Regioselective tosylation of (XV), followed by hydrogenation of the resulting monotosylate (XVI) over Pd/C, leads to (1S,2R)-2-hydroxycyclohexyl tosylate (XVII). Subsequent coupling of (XVII) with imidate (X) provides the target intermediate (I) (1). In a different method, ketalization of (S,S)-1,2-cyclohexanediol (XVIII) with 2,2-dimethoxypropane provides the acetonide (XIX), which is oxidized to 2(S)-hydroxycyclohexanone (XX) by treatment with bis(trifluoromethyl)-dioxirane (BTDO). Subsequent tosylation of (XX) furnishes 2(S)-tosyloxycyclohexanone (XXI). Alternatively, the chiral tosyl ketone (XXI) can be obtained by monotosylation of diol (XVIII) in the presence of Bu2SnO to afford the hydroxy tosylate (XXII), which is subjected to Jones oxidation, giving ketone (XXI). The diastereoselective reduction of ketone (XXI) then provides an alternative route to 2(R)-hydroxy tosylate (XVII). Alternatively, the chiral tosyl ketone (XXI) is condensed with the sodium alkoxide of 3,4-dimethoxyphenethyl alcohol (XI) to yield the 2(R)-ether (XXIIIa). Stereoselective reduction of ketone (XXIIIa) utilizing bulky reducing agents such as L-Selectride, LS-Selectride or alpine boranes gives the (S)-cyclohexanol (XXIV), which can be further converted to tosylate (I) under the usual conditions. Similarly, the phenethyl alcohol (XI) can be reacted with 2-chlorocyclohexanone (XXV) by means of NaH to yield the racemic ketone ether (XXIIIb), which is enantioselectively reduced to the (1S,2R)-phenethoxycyclohexanol (XXIV) under Noyori’s asymmetric hydrogenation conditions. A further route to the phenethoxy ketone (XXIIIa) consists of the enantioselective α-oxyamination of cyclohexanone (XXVI) with nitrosobenzene in the presence of L-proline to produce the chiral hydroxylamine derivative (XXVII), which is subsequently cleaved to 2(R)-hydroxycyclohexanone (XXVIII) by treatment with CuSO4, and then coupled with imidate (X) in the presence of boron trifluoride etherate. Optionally, 2(R)-hydroxycyclohexanone (XXVIII) can be obtained by oxidation of the (1R,2R)-cyclohexanediol acetonide (XXIX) with BTDO. Another method for obtaining the (1S,2R)-phenethoxy cyclohexanol (XXIV) is based on the asymmetric reduction of (3,4-dimethoxyphenyl)acetaldehyde cyclohexanediol acetal (XXX) by means of triethylsilane in the presence of chiral Lewis acids (2). Scheme 2.

参考文献中间体

【1】 Beatch, G.N., Choi, L.S.L., Jung, G. et al. (Cardiome Pharma Corp.). Aminocyclohexyl ether compounds and uses thereof. EP 1560812, EP1666459, JP 2006525227, WO 2004099137.
【2】 Plouvier, B.M.C., Chou, D.T.H., Jung, G. et al. (Cardiome Pharma Corp.). Synthetic process for aminocyclohexyl ether compounds. WO 2006088525.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XXIIIa)	65283			C₁₆H₂₂O₄	详情	详情
(XXIIIb)	65284			C₁₆H₂₂O₄	详情	详情
(I)	65263	(1S,2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexyl tosylate		C₂₃H₃₀O₆S	详情	详情
(X)	65272	3,4-dimethoxyphenethyl trichloroacetimidate		C₁₂H₁₄Cl₃NO₃	详情	详情
(XIII)	10190	1-Chlorobenzene	108-90-7	C₆H₅Cl	详情	详情
(XIV)	65274	(1S,2S)-3-chlorocyclohexa-3,5-diene-1,2-diol		C₆H₇ClO₂	详情	详情
(XV)	65275	(1S,2S)-3-chlorocyclohexa-3-ene-1,2-diol		C₆H₉ClO₂	详情	详情
(XVI)	65276	(1S,2S)-3-chloro-2-hydroxycyclohexa-3-ene-1-yl tosylate		C₁₃H₁₅ClO₄S	详情	详情
(XVII)	65277	(1S,2R)-2-hydroxycyclohexyl tosylate		C₁₃H₁₈O₄S	详情	详情
(XVIII)	65278	(1R,2R)-1,2-Cyclohexanediol	1072-86-2	C₆H₁₂O₂	详情	详情
(XIX)	65279	(1S,2S)-cyclohexanediol acetonide		C₉H₁₆O₂	详情	详情
(XX)	65280	(2S)-hydroxycyclohexanone		C₆H₁₀O₂	详情	详情
(XXI)	65281	(2S)-tosyloxycyclohexanone		C₁₃H₁₆O₄S	详情	详情
(XXII)	65282	(1S,2S)-2-hydroxycyclohexyl tosylate		C₁₃H₁₈O₄S	详情	详情
(XXIV)	65285	(1S,2R)-phenethoxycyclohexanol		C₁₆H₂₄O₄	详情	详情
(XXV)	17985	2-Chlorocyclohexanone	822-87-7	C₆H₉ClO	详情	详情
(XXVI)	11059	Cyclohexanone	108-94-1	C₆H₁₀O	详情	详情
(XXVII)	65286			C₁₂H₁₅NO₂	详情	详情
(XXVIII)	65287	(2R)-hydroxycyclohexanone		C₆H₁₀O₂	详情	详情
(XXIX)	65288	(1R,2R)-cyclohexanediol acetonide		C₉H₁₆O₂	详情	详情
(XXX)	65289	(3,4-dimethoxyphenyl)acetaldehyde cyclohexanediol acetal		C₁₆H₂₁O₄	详情	详情

合成路线3

The precursor (1R,2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexylamine (V) can be prepared as follows. Ring opening of cyclohexene oxide (XXXI) with benzylamine affords racemic trans-2-benzylaminocyclohexanol (XXXII) which, after resolution with L-(–)-di-p-toluoyltartaric acid, is treated with benzyl chloroformate to produce the chiral carbamate (XXXIII). Subsequent condensation of the cyclohexanol derivative (XXXIII) with imidate (X) yields the dimethoxyphenethyl ether (XXXIV), from which the N-benzyl and carbobenzoxy protecting groups are removed by hydrogenolysis over Pd/C to furnish the target intermediate (V). Similarly, ring opening of epoxide (XXXI) with trimethylsilyl azide utilizing either Jacobsen’s (salen)Cr(III) catalyst or Nugent’s Zr C3-symmetrical complex, followed by acidic desilylation, furnishes (R,R)-2-azidocyclohexanol (XXXV). After coupling of (XXXV) with imidate (X), catalytic hydrogenation of the resulting azido ether (XXXVI) provides amine (V). In an alternative method, aminolysis of cyclohexene oxide (XXXI) produces racemic trans-2-aminocyclohexanol (XXXVII), which, after resolution with L-tartaric acid, is reacted with benzyl chloroformate to give (R,R)-2-(benzyloxycarbonylamino)cyclohexanol (XXXVIII). Optionally, the chiral carbamate (XXXVIII) can be obtained by reaction of racemic aminocyclohexanol (XXXVII) with benzyl chloroformate, followed by enantioselective acetylation of the obtained compound (XXXIX) with vinyl acetate in the presence of lipase, to furnish the (R,R)-acetate (XL), which is then hydrolyzed to (XXXVIII) under alkaline conditions. Coupling of (R,R)-2-(benzyloxycarbonylamino)cyclohexanol (XXXVIII) with imidate (X) produces the carbobenzoxy-protected amino ether (XLI), which is then hydrolyzed to (V) in refluxing 6N HCl. A different route to the intermediate amine (V) consists of displacement of tosylate (I) with NaN3, followed by catalytic hydrogenation of the resulting alkyl azide (2). Scheme 3.

参考文献中间体

【2】 Plouvier, B.M.C., Chou, D.T.H., Jung, G. et al. (Cardiome Pharma Corp.). Synthetic process for aminocyclohexyl ether compounds. WO 2006088525.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	65263	(1S,2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexyl tosylate		C₂₃H₃₀O₆S	详情	详情
(V)	65266	(1R,2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexylamine		C₁₆H₂₅NO₃	详情	详情
(X)	65272	3,4-dimethoxyphenethyl trichloroacetimidate		C₁₂H₁₄Cl₃NO₃	详情	详情
(XXXI)	17986	7-oxabicyclo[4.1.0]heptane; cyclohexene oxide	286-20-4	C₆H₁₀O	详情	详情
(XXXII)	65290	racemic trans-2-benzylaminocyclohexanol		C₁₃H₁₈NO	详情	详情
(XXXIII)	65291			C₂₁H₂₄NO₃	详情	详情
(XXXIV)	65292			C₃₁H₃₆NO₅	详情	详情
(XXXV)	65293	(R,R)-2-azidocyclohexanol		C₆H₁₁N₃O	详情	详情
(XXXVI)	65294			C₁₆H₂₂N₃O₃	详情	详情
(XXXVII)	65295	racemic trans-2-aminocyclohexanol	6850-38-0	C₆H₁₃NO	详情	详情
(XXXVIII)	65296	(R,R)-2-(benzyloxycarbonylamino)cyclohexanol		C₁₄H₁₉NO₃	详情	详情
(XXXIX)	65297	(RS,RS)-2-(benzyloxycarbonylamino)cyclohexanol		C₁₄H₁₉NO₃	详情	详情
(XL)	65298	(R,R)-2-(benzyloxycarbonylamino)cyclohexanyl acetate		C₁₆H₂₁NO₄	详情	详情
(XLI)	65299			C₂₄H₃₁NO₅	详情	详情

合成路线4

Several alternative routes to the intermediate amine (V) are shown in Scheme 4. The asymmetric reduction of ethyl 2-oxocyclohexanecarboxylate (XLII) gives the (1R,2S)-hydroxy ester (XLIII), which is converted to amide (XLIV) by treatment with aqueous ammonia and ammonium chloride. After activation of the hydroxyl group of (XLIV) as the corresponding mesylate (XLV), displacement with the potassium alkoxide of 3,4-dimethoxyphenethyl alcohol (XI) affords the trans-amide ether (XLVI). The target amine (V) is then obtained by Hofmann rearrangement of carboxamide (XLVI) employing NaOCl and NaOH. A different resolution method involves transesterification of ethyl 2-oxocyclohexanecarboxylate (XLII) with benzyl alcohol, followed by enzymatic reduction of the resulting benzyl keto ester (XLVII) with carbonyl reductase to provide the (1R,2R)-hydroxy ester (XLVIII). Coupling of (XLVIII) with imidate (X) furnishes the benzyl phenethoxycyclohexanecarboxylate (XLIX), which is subjected to benzyl group hydrogenolysis to provide acid (L). This compound can also be obtained by condensation of ethyl 2(R)-hydroxy-1(R)-cyclohexanecarboxylate (LI) with 3,4-dimethoxyphenethyl trichloroacetimidate (X), followed by alkaline hydrolysis of the obtained ethyl 2-phenethoxycyclohexanecarboxylate (LII). Optionally, the ethyl ester (LII) can be converted to amide (XLVI) by reaction with methanolic ammonia, or to hydrazide (LIII) by treatment with hydrazine hydrate in EtOH. Conversion of acid (L) to the target amine (V) can then be accomplished by Curtius rearrangement employing diphenylphosphoryl azide. Analogously, diazotization of hydrazide (LIII), followed by Curtius rearrangement of the intermediate acyl azide and alkaline hydrolysis results in the target amine (V) (2). Scheme 4.

参考文献中间体

【2】 Plouvier, B.M.C., Chou, D.T.H., Jung, G. et al. (Cardiome Pharma Corp.). Synthetic process for aminocyclohexyl ether compounds. WO 2006088525.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	65266	(1R,2R)-2-[2-(3,4-dimethoxyphenyl)ethoxy]cyclohexylamine		C₁₆H₂₅NO₃	详情	详情
(X)	65272	3,4-dimethoxyphenethyl trichloroacetimidate		C₁₂H₁₄Cl₃NO₃	详情	详情
(XI)	38711	2-(3,4-dimethoxyphenyl)-1-ethanol	7417-21-2	C₁₀H₁₄O₃	详情	详情
(XLII)	11889	ethyl 2-oxocyclohexanecarboxylate; Ethyl 2-cyclohexanonecarboxylate	1655-07-8	C₉H₁₄O₃	详情	详情
(XLIII)	15589	ethyl 2-hydroxycyclohexanecarboxylate; Ethyl cis-2-hydroxy-1-cyclohexanecarboxylate	6149-52-6	C₉H₁₆O₃	详情	详情
(XLIV)	65300	cis-2-Hydroxy-1-Cyclohexanecarboxamide; (1R,2S)-2-Hydroxy-1-Cyclohexanecarboxamide; Zinc01081409	73045-98-4	C₇H₁₃NO₂	详情	详情
(XLV)	65301			C₇H₁₂NaNO₂	详情	详情
(XLVI)	65302			C₁₇H₂₅NO₄	详情	详情
(XLVII)	65303			C₁₄H₁₆O₃	详情	详情
(XLVIII)	65304			C₁₄H₁₈O₃	详情	详情
(XLIX)	65305			C₂₄H₃₀O₅	详情	详情
(L)	65306			C₁₆H₂₄O₅	详情	详情
(LI)	65307	Ethyl trans-2-hydroxycyclohexanecarboxylate	3444-72-2	C₉H₁₆O₃	详情	详情
(LII)	65308			C₁₉H₂₈O₅	详情	详情
(LIII)	65309			C₁₇H₂₆N₂O₄	详情	详情

合成路线5

The pyrrolidine building blocks are in turn synthesized as shown in Scheme 5. 3(R)-Hydroxypyrrolidine (IV) is protected as the N-Boc derivative (LIV), followed by O-alkylation with benzyl bromide and acidic deprotection of the resulting benzyl ether (LV) to furnish 3(R)-benzyloxypyrrolidine (II). Condensation of pyrrolidine (II) with cyclohexene oxide (XXXI) gives the trans-pyrrolidinocyclohexanol (LVI) as a diastereomeric mixture, which is separated either by crystallization with di-p-toluoyl-L-tartaric acid (DTTA) or by diastereoselective N-oxidation of the undesired diastereoisomer to furnish the target isomer (IX). Alternatively, intermediate (IX) can be obtained by ring opening of epoxide (XXXI) with pyrrolidine (II) in the presence of chiral catalysts. In a different strategy, enantioselective ring opening of cyclohexene oxide (XXXI) with B-bromodiisopinocamphenylborane provides the optically enriched trans-bromohydrin (LVII), which is then condensed with benzyloxypyrrolidine (II) to yield the (1S,2R)-pyrrolidinocyclohexanol (LVIII). Inversion of the configuration of alcohol (LVIII) to produce (IX) is then accomplished by Mitsunobu coupling with formic acid, followed by acidic hydrolysis of the resulting (1R,2R)-formate ester (LIX). Further synthetic strategies leading to the pyrrolidinocyclohexanol (IX) involve cyclization of (R,R)-2-aminocyclohexanol (LX) with 2(R)-benzyloxy-1,4-butanediol ditosylate (LXI), and condensation of (LX) with cyclohexanone (XXVI), followed by asymmetric hydroboration and oxidative work-up of the resulting enamine (LXII) (2). Alternatively, (R,R)-2-aminocyclohexanol (LX) can be converted to the intermediate acetoxysuccinimide (XII) by condensation with 2(R)-acetoxysuccinic anhydride (VI) (prepared from L-malic acid [LXIII] and acetyl chloride) to produce a regioisomeric mixture of succinamic acids (LXIVa) and (LXIVb), which undergoes cyclization to imide (XII) upon heating with acetyl chloride (4). Similarly, racemic trans-2-benzyloxycyclohexylamine (LXV) is resolved by enantioselective N-acylation with isopropyl methoxyacetate in the presence of lipase, followed by hydrolysis of the resulting (R,R)-methoxyacetamide (LXVI) to provide (LXVII) (5). Acylation of (R,R)-2-benzyloxycyclohexylamine (LXVII) with O-acetylmalic anhydride (VI), followed by cyclization with acetyl chloride, yields the N-(2-benzyloxycyclohexyl)succinimide (LXVIII), which is then debenzylated to (XII) by catalytic hydrogenation over Pd/C (4). Scheme 5.

参考文献中间体

【2】 Plouvier, B.M.C., Chou, D.T.H., Jung, G. et al. (Cardiome Pharma Corp.). Synthetic process for aminocyclohexyl ether compounds. WO 2006088525.
【4】 Roth, C.J., Jung, G., Plouvier, B.M.C., Chou, D.T.H., Yee, J.G.K. (Cardiome Pharma Corp.). Synthetic processes for the preparation of aminocyclohexyl ether compounds. WO 2006138673.
【5】 Balkenhohl, F., Ditrich, K., Nübling, C. (BASF AG). Racemate separation of primary and secondary heteroatom-substituted amine by enzyme-catalysed acylation. WO 9623894.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(LXIVa)	65319			C₁₂H₁₉NO₆	详情	详情
(LXIVb)	65320			C₁₂H₁₉NO₆	详情	详情
(II)	65264	(3R)-benzyloxypyrrolidine		C₁₁H₁₅NO	详情	详情
(IV)	14490	(3R)tetrahydro-1H-pyrrol-3-ol; R-3-hydroxypyrrolidine	2799-21-5	C₄H₉NO	详情	详情
(VI)	65267	(2R)-acetoxysuccinic anhydride	79814-40-7	C₆H₆O₅	详情	详情
(VI)	51236	2,4-Dimethylpyrrole	625-82-1	C₆H₉N	详情	详情
(IX)	65271	(2R)-[(3R)-benzyloxy-1-pyrrolidinyl]cyclohexan-(1R)-ol		C₁₆H₂₅NO₂	详情	详情
(XII)	65273	(2R)-acetoxy-N-[(2R)-hydroxy-(1R)-cyclohexyl]succinimide		C₁₂H₁₇O₅	详情	详情
(XXVI)	11059	Cyclohexanone	108-94-1	C₆H₁₀O	详情	详情
(XXXI)	17986	7-oxabicyclo[4.1.0]heptane; cyclohexene oxide	286-20-4	C₆H₁₀O	详情	详情
(LIV)	65310	(R )-1-Boc-3-hydroxypyrrolidine; (R )-N-(tert-Butoxycarbonyl)-3-hydroxypyrrolidine; (R )-3-Hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester	103057-44-9	C₉H₁₇O₃N	详情	详情
(LV)	65311			C₁₆H₂₃O₃N	详情	详情
(LVI)	65312			C₁₇H₂₅NO₂	详情	详情
(LVII)	65313	trans-2-bromocyclohexanol		C₆H₁₁BrO	详情	详情
(LVIII)	65314			C₁₇H₂₄NO₂	详情	详情
(LIX)	65315			C₁₈H₂₅NO₃	详情	详情
(LX)	65316	(1R,2R)-2-aminocyclohexanol		C₆H₁₃NO	详情	详情
(LXI)	65317			C₂₅H₂₈O₇S₂	详情	详情
(LXII)	65318			C₁₇H₂₃NO	详情	详情
(LXIII)	11058	(S)-(+)-Hydroxysuccinic acid; (S)-(+)-Malic acid; (S)-(+)-2-Hydroxybutanedioic acid; L-(-)-Apple acid	97-67-6	C₄H₆O₅	详情	详情
(LXV)	65321	racemic trans-2-benzyloxycyclohexylamine		C₁₃H₁₇NO	详情	详情
(LXVI)	65322			C₁₆H₂₃NO₃	详情	详情
(LXVII)	65323			C₁₃H₁₉NO	详情	详情
(LXVIII)	65324			C₁₉H₂₃NO₅	详情	详情

Extended Information

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