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【结 构 式】

【分子编号】43629

【品名】N-[(1R)-1-[(3aR,6R,6aR)-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1-[(benzyloxy)methyl]-2-propenyl]-2,2,2-trichloroacetamide

【CA登记号】

【 分 子 式 】C21H26Cl3NO5

【 分 子 量 】478.79928

【元素组成】C 52.68% H 5.47% Cl 22.21% N 2.93% O 16.71%

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:(XLVIa)

Treatment of allofuranose derivative (XXXIX) with Bu2SnO in toluene followed by treatment with benzyl bromide and CsF provides (XL), which is then oxidized with Jones reagent to afford ketone (XLI). Wittig reaction of (XLI) with (ethoxycarbonymethylene)triphenylphosphorane (XLII) in toluene yields olefin (XLIII), which is then reduced by means of DIBAL to give (XLIV). Alcohol (XLIV) is then converted into trichloroacetimidate (XLV) by treatment with NaH and trichloroacetonitrile (CCl3CN) in Et2O. Rearrangement of (XLV) by heating with toluene affords derivative (XLVI), which is hydrolyzed by means of TFA/H2O to yield a mixture of diols that are chromatographically separated, providing (XLVII). Oxidation of (XLVII) in MeOH by means of NaIO4 provides hemiaminal derivative (XLVIII), which is further oxidized with Jones reagent to afford lactam (IL). Removal of protecting (N-trichloroacetyl and O-formyl) groups by treatment of (IL) with NaBH4 in MeOH gives partially deprotected derivative (L).

1 Chida, N.; et al.; Stereoselective total synthesis of (+)-lactacystin from D-glucose. Tetrahedron 1997, 53, 48, 16287.
2 Corey, E.J.; Li, W.-D.Z.; Total synthesis and biological activity of lactacystin, omuralide and analogs. Chem Pharm Bull 1999, 47, 1, 1.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XLIIIa) 43623 ethyl (E)-3-[(3aR,6R,6aR)-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-4-(benzyloxy)-2-butenoate C21H28O6 详情 详情
(XLIIIb) 43624 ethyl (Z)-3-[(3aR,6R,6aR)-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-4-(benzyloxy)-2-butenoate C21H28O6 详情 详情
(XLIVa) 43625 (Z)-3-[(3aR,5S,6R,6aR)-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-4-(benzyloxy)-2-buten-1-ol C19H26O5 详情 详情
(XLIVb) 43626 (E)-3-[(3aR,5S,6R,6aR)-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-4-(benzyloxy)-2-buten-1-ol C19H26O5 详情 详情
(XLVa) 43627 (Z)-3-[(3aR,5S,6R,6aR)-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-4-(benzyloxy)-2-butenyl 2,2,2-trichloroethanimidoate C21H26Cl3NO5 详情 详情
(XLVb) 43628 (E)-3-[(3aR,5S,6R,6aR)-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-4-(benzyloxy)-2-butenyl 2,2,2-trichloroethanimidoate C21H26Cl3NO5 详情 详情
(XLVIa) 43629 N-[(1R)-1-[(3aR,6R,6aR)-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1-[(benzyloxy)methyl]-2-propenyl]-2,2,2-trichloroacetamide C21H26Cl3NO5 详情 详情
(XLVIb) 43630 N-[(1S)-1-[(3aR,6R,6aR)-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1-[(benzyloxy)methyl]-2-propenyl]-2,2,2-trichloroacetamide C21H26Cl3NO5 详情 详情
(XLVIIIa) 43632 (2R,3S,4R,5R)-2-[(benzyloxy)methyl]-5-hydroxy-4-methyl-1-(2,2,2-trichloroacetyl)-2-vinylpyrrolidinyl formate C18H20Cl3NO5 详情 详情
(XLVIIIb) 43633 (2R,3S,4R,5S)-2-[(benzyloxy)methyl]-5-hydroxy-4-methyl-1-(2,2,2-trichloroacetyl)-2-vinylpyrrolidinyl formate C18H20Cl3NO5 详情 详情
(IL) 43634 (2R,3S,4R)-2-[(benzyloxy)methyl]-4-methyl-5-oxo-1-(2,2,2-trichloroacetyl)-2-vinylpyrrolidinyl formate C18H18Cl3NO5 详情 详情
(XXXIX) 43620 (1R)-1-[(3aR,6R,6aR)-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-1,2-ethanediol C10H18O5 详情 详情
(XL) 43621 (1R)-1-[(3aR,6R,6aR)-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-(benzyloxy)-1-ethanol C17H24O5 详情 详情
(XLI) 43622 1-[(3aR,6R,6aR)-2,2,6-trimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-(benzyloxy)-1-ethanone C17H22O5 详情 详情
(XLII) 14182 ethyl 2-(triphenyl-lambda(5)-phosphanylidene)acetate; (Carbethoxymethylene)triphenylphosphorane 1099-45-2 C22H21O2P 详情 详情
(XLVII) 43631 N-[(1R)-1-[(benzyloxy)methyl]-1-[(3S,4R,5S)-4,5-dihydroxy-3-methyltetrahydro-2-furanyl]-2-propenyl]-2,2,2-trichloroacetamide C18H22Cl3NO5 详情 详情
(L) 43635 (3R,4S,5R)-5-[(benzyloxy)methyl]-4-hydroxy-3-methyl-5-vinyl-2-pyrrolidinone C15H19NO3 详情 详情
Extended Information