2,4,6-triisopropylbenzenesulfonyl chloride -Drug Synthesis Database

【结构式】

【分子编号】14545

【品名】2,4,6-triisopropylbenzenesulfonyl chloride

【CA登记号】6553-96-4

【分子式】C₁₅H₂₃ClO₂S

【分子量】302.86512

【元素组成】C 59.49% H 7.65% Cl 11.71% O 10.57% S 10.59%

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：(XXX)

4) The selective esterification of 3(S)-azido-4-phenylbutane-1,2(S)-diol (XXIX) with 2,4,6-triiosopropylbenzenesulfonyl chloride (XXX) gives the sulfonate ester (XXXI), which by treatment with KOH is converted to the azido epoxide (XXXII). The condensation of (XXXII) with decahydroisoquinoline (XI) affords the azido condensation product (XXXIII), which is finally hydrogenated with H2 over Pd/C to the amino condensation product (XIII), already obtained in scheme 16810301a. 5) The reaction of (XXIX) with SOCl2 and RuCl3 gives the dioxathiole dioxide (XXXIV), which is condensed with decahydroisoquinoline (XI) to afford the azido condensation product (XXXIII), already obtained.

参考文献中间体

合成目标

【1】 Parkes, K.E.B.; Bushnell, D.J.; Crackett, P.H.; et al.; Studies toward the large-scale synthesis of the HIV proteinase inhibitor Ro 31-8959. J Org Chem 1994, 59, 13, 3656.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XI)	13955	(3S,4aS,8aS)-N-(tert-Butyl)decahydro-3-isoquinolinecarboxamide		C₁₄H₂₆N₂O	详情	详情
(XIII)	14528	(3S,4aS,8aS)-2-[(2R,3S)-3-amino-2-hydroxy-4-phenylbutyl]-N-(tert-butyl)decahydro-3-isoquinolinecarboxamide		C₂₄H₃₉N₃O₂	详情	详情
(XXIX)	14544	(2S,3S)-3-azido-4-phenyl-1,2-butanediol		C₁₀H₁₃N₃O₂	详情	详情
(XXX)	14545	2,4,6-triisopropylbenzenesulfonyl chloride	6553-96-4	C₁₅H₂₃ClO₂S	详情	详情
(XXXI)	14546	(2S,3S)-3-azido-2-hydroxy-4-phenylbutyl 2,4,6-triisopropylbenzenesulfonate		C₂₅H₃₅N₃O₄S	详情	详情
(XXXII)	14547	(1S)-1-[(2S)oxiranyl]-2-phenylethyl azide; (2S)-2-[(1S)-1-azido-2-phenylethyl]oxirane		C₁₀H₁₁N₃O	详情	详情
(XXXIII)	14548	(3S,4aS,8aS)-2-[(2R,3S)-3-(1-azanylhydrazino)-2-hydroxy-4-phenylbutyl]-N-(tert-butyl)decahydro-3-isoquinolinecarboxamide		C₂₄H₄₁N₅O₂	详情	详情
(XXXIV)	14549	(4S)-4-[(1S)-1-azido-2-phenylethyl]-1,3,2lambda(6)-dioxathiolane-2,2-dione		C₁₀H₁₁N₃O₄S	详情	详情

合成路线2

该中间体在本合成路线中的序号：(II)

Treatment of 2',3'-O-isopropylidene-5'-O-trityluridine (I) with 2,4,6-triisopropylbenzenesulfonyl chloride (II) in the presence of DMAP affords the sulfonic ester derivative (III). Subsequent displacement of sulfonate (III) with hydroxylamine leads to the protected N-hydroxycytidine (IV). The protecting groups of (IV) are finally removed with aqueous trifluoroacetic acid to furnish the title compound.

参考文献中间体

合成目标

【1】 Watanabe, K.A.; Stuyver, L. (Pharmasset, Inc.); Modified nucleosides for treatment of viral infections and abnormal cellular proliferation. WO 0232920 .

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)	64247	1-{(3aR,4R,6R,6aR)-2,2-dimethyl-6-[(trityloxy)methyl]tetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-2,4(1H,3H)-pyrimidinedione		C₃₁H₃₀N₂O₆	详情	详情
(II)	14545	2,4,6-triisopropylbenzenesulfonyl chloride	6553-96-4	C₁₅H₂₃ClO₂S	详情	详情
(III)	64248	1-{(3aR,4R,6R,6aR)-2,2-dimethyl-6-[(trityloxy)methyl]tetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-2-oxo-1,2-dihydro-4-pyrimidinyl 2,4,6-triisopropylbenzenesulfonate		C₄₆H₅₂N₂O₈S	详情	详情
(IV)	64249	1-{(3aR,4R,6R,6aR)-2,2-dimethyl-6-[(trityloxy)methyl]tetrahydrofuro[3,4-d][1,3]dioxol-4-yl}-4-(hydroxyamino)-2(1H)-pyrimidinone		C₃₁H₃₁N₃O₆	详情	详情

Extended Information