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【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

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.

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.

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