diallyl (2S)-2-isocyanatopentanedioate -Drug Synthesis Database

【结构式】

【分子编号】34431

【品名】diallyl (2S)-2-isocyanatopentanedioate

【CA登记号】

【分子式】C₁₂H₁₅NO₅

【分子量】253.25484

【元素组成】C 56.91% H 5.97% N 5.53% O 31.59%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(II)

Coupling of 4-aminobenzyl alcohol (I) with diallyl L-glutamylisocyanate (II) produced the urea derivative (III). Subsequent activation of the benzylic alcohol group with 4-nitrophenyl chloroformate (IV) afforded carbonate (V). This was then condensed with doxorubicin (VI) to furnish the corresponding carbamate (VII). Finally, palladium-catalyzed cleavage of the allyl esters of (VII) yielded the title compound.

参考文献中间体

合成目标

【1】 Friedlos, F.; Spooner, R.; Marais, R.; Springer, C.J.; Martin, J.; Niculescu-Duvaz, I.; Niculescu-Duvaz, D.; Self-immolative anthracycline prodrugs for suicide gene therapy. J Med Chem 1999, 42, 13, 2485.

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)	34430	(4-aminophenyl)methanol	623-04-1	C₇H₉NO	详情	详情
(II)	34431	diallyl (2S)-2-isocyanatopentanedioate		C₁₂H₁₅NO₅	详情	详情
(III)	34432	diallyl (2S)-2-([[4-(hydroxymethyl)anilino]carbonyl]amino)pentanedioate		C₁₉H₂₄N₂O₆	详情	详情
(IV)	16605	4-Nitrophenyl chloroformate; 1-[(Chlorocarbonyl)oxy]-4-nitrobenzene	7693-46-1	C₇H₄ClNO₄	详情	详情
(V)	34433	diallyl (2S)-2-([[4-([[(4-nitrophenoxy)carbonyl]oxy]methyl)anilino]carbonyl]amino)pentanedioate		C₂₆H₂₇N₃O₁₀	详情	详情
(VI)	11675	(8S,10S)-10-[[(2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl]oxy]-8-glycoloyl-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydro-5,12-naphthacenedione		C₂₇H₂₉NO₁₁	详情	详情
(VII)	34434			C₄₇H₅₁N₃O₁₈	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

The intermediate benzaldehyde (XII) has been obtained as follows: The reduction of 4-nitrobenzaldehyde (I) with NaBH4 and NiCl2 gives 4-aminobenzyl alcohol (II), which is treated with benzyl chloroformate to yield the carbamate (III). The protection of the OH group of (III) with Tbdms-Cl affords the silyl ether (IV). The cyclization of (IV) with glycidyl butyrate (V) by means of BuLi provides the hydroxymethyl oxazolidinone (VI), which is treated with MsCl and TEA to give the mesylate (VII). The reaction of (VII) with NaN3 yields the azidomethyl compound (VIII), which is condensed with thioacetic acid (IX) to afford the acetamide (X). The cleavage of the Tbdms protecting group of (X) by means of TBAF provides the benzyl alcohol (XI), which is oxidized with PDC to furnish the target benzaldehyde intermediate (XII)

参考文献中间体

合成目标

【1】 Selvakumar, N.; et al.; Synthesis and antibacterial activity of novel chalcone oxazolidinone hybrids. 42nd Intersci Conf Antimicrob Agents Chemother (Sept 27 2002, San Diego) 2002, Abst F-1323.

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)	18184	4-Nitrobenzaldehyde	555-16-8	C₇H₅NO₃	详情	详情
(II)	34431	diallyl (2S)-2-isocyanatopentanedioate		C₁₂H₁₅NO₅	详情	详情
(III)	61803	benzyl 4-(hydroxymethyl)phenylcarbamate		C₁₅H₁₅NO₃	详情	详情
(IV)	61804	benzyl 4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenylcarbamate		C₂₁H₂₉NO₃Si	详情	详情
(V)	18385	(2R)oxiranylmethyl butyrate;(R)-glycidyl butyrate	60456-26-0	C₇H₁₂O₃	详情	详情
(VI)	61805	(5R)-3-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one		C₁₇H₂₇NO₄Si	详情	详情
(VII)	61806	{(5R)-3-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl methanesulfonate		C₁₈H₂₉NO₆SSi	详情	详情
(VIII)	61807	(5R)-5-(azidomethyl)-3-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]-1,3-oxazolidin-2-one		C₁₇H₂₆N₄O₃Si	详情	详情
(IX)	12893	Ethanethioic S-acid		C₂H₄OS	详情	详情
(X)	61808	N-({(5S)-3-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide		C₁₉H₃₀N₂O₄Si	详情	详情
(XI)	61809	N-({(5S)-3-[4-(hydroxymethyl)phenyl]-2-oxo-1,3-oxazolidin-5-yl}methyl)acetamide		C₁₃H₁₆N₂O₄	详情	详情
(XII)	61812	N-{[(5S)-3-(4-formylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl}acetamide		C₁₃H₁₄N₂O₄	详情	详情

Extended Information