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【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.

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 CAS号 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
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