(1R,2S,3S,4R,6R)-2,3,4,6-tetrakis(benzyloxy)cyclohexanol -Drug Synthesis Database

【结构式】

【分子编号】40714

【品名】(1R,2S,3S,4R,6R)-2,3,4,6-tetrakis(benzyloxy)cyclohexanol

【CA登记号】

【分子式】C₃₄H₃₆O₅

【分子量】524.65684

【元素组成】C 77.84% H 6.92% O 15.25%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号：(I)

Phosphitylation of 1D-2,4,5,6-tetra-O-benzyl-3-deoxy-myo-inositol (I) with benzyl tetraisopropylphosphorodiamidite (II) in the presence of diisopropylammonium tetrazolide produced phosphoramidite (III). Subsequent displacement of the remaining diisopropylamino group of (III) by 1-O-octadecyl-2-O-methyl-sn-glycerol (IV) gave phosphite ester (V), which was further oxidized to phosphate (VI) using tert-butyl hydroperoxide. Finally, removal of the benzyl protecting groups of (VI) was achieved by catalytic hydrogenation over Pearlman's catalyst.

参考文献中间体

合成目标

【1】 Qiao, L.; Nan, F.; Kunkel, M.; Gallegos, A.; Powis, G.; Kozikowski, A.P.; 3-Deoxy-D-myo-inositol 1-phosphate, 1-phosphonate, and ether lipid analogues as inhibitors of phosphatidylinositol-3-kinase signalling and cancer cell growth. J Med Chem 1998, 41, 18, 3303.
【2】 Powis, G.; Qioa, L.; Kozikowski, A.P. (Georgetown University); Inhibitors of phosphatidyl myo-inositol cycle. WO 0000206 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	40714	(1R,2S,3S,4R,6R)-2,3,4,6-tetrakis(benzyloxy)cyclohexanol	C₃₄H₃₆O₅	详情	详情
(II)	40715		C₁₃H₂₃N₂OP	详情	详情
(III)	40716		C₄₄H₅₀NO₆P	详情	详情
(IV)	40717	(2S)-2-methoxy-3-(octadecyloxy)-1-propanol	C₂₂H₄₆O₃	详情	详情
(V)	40718	benzyl (2R)-2-methoxy-3-(octadecyloxy)propyl (1R,2R,3S,4R,6R)-2,3,4,6-tetrakis(benzyloxy)cyclohexyl phosphite	C₆₃H₈₇O₉P	详情	详情
(VI)	40719	benzyl (2R)-2-methoxy-3-(octadecyloxy)propyl (1R,2R,3S,4R,6R)-2,3,4,6-tetrakis(benzyloxy)cyclohexyl phosphate	C₆₃H₈₇O₁₀P	详情	详情

Extended Information