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【结 构 式】

【分子编号】64911

【品名】2-methyl 1-(phenylmethyl) 5,6-dihydroxyoctahydro-1H-indole-1,2-dicarboxylate

【CA登记号】

【 分 子 式 】C18H23NO6

【 分 子 量 】349.38376

【元素组成】C 61.88% H 6.64% N 4.01% O 27.48%

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:(XI)

Synthesis of the perhydroindole intermediate (XIII): The alkylation of the N-protected glutamate (I) with allyl bromide (II) by means of LiHMDS in THF gives the protected chiral allyl glutamate (III) (1), which is cyclized by means of TFA in dichloromethane to yield the pyroglutamate (IV). The reduction of (IV) with LiHBEt3 in THF affords the hydroxy compound (V), which is treated with Ac2O and DMAP in dichloromethane to provide the expected hemiaminal derivative (VI). The reaction of (VI) with allyl tributylstannane (VII) by means of BF3/Et2O in toluene gives the diallyl pyrrolidine (VIII), which is submitted to a ring closure by olefin metathesis using a Grubbs Ru catalyst in dichloromethane to yield the hexahydroindole derivative (IX). The reaction of (IX) with mCPBA in dichloromethane affords the epoxide (X), which is hydrolyzed with TFA to yield the dihydroxy compound (XI). The reaction of (XI) with Mom-Cl and DIEA in dichloromethane provides the bis mom ether (XII), which is treated with H2 over Pd/C in methanol to yield the desired perhydroindole intermediate (XIII) (2).

1 Hanessian, S.; Margarita, R.; 1,3-Asymmetric induction in dianionic allylation reactions of amino acid derivatives-synthesis of functionally useful enantiopure glutamates, pipecolates and pyroglutamates. Tetrahedron Lett 1998, 39, 33, 5887.
2 Hanessian, S.; Margarita, R.; Hall, A.; Johnstone, S.; Tremblay, M.; Parlanti, L.; Total synthesis and structural confirmation of the marine natural product Dysinosin A: A novel inhibitor of thrombin and Factor VIIa. J Am Chem Soc 2002, 124, 45, 13342.
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) 64903 dimethyl 2-({[(phenylmethyl)oxy]carbonyl}amino)pentanedioate C15H19NO6 详情 详情
(II) 11463 3-Bromo-1-propene; 3-Bromopropene;allyl bromide 106-95-6 C3H5Br 详情 详情
(III) 64904 dimethyl 2-({[(phenylmethyl)oxy]carbonyl}amino)-4-(2-propenyl)pentanedioate C18H23NO6 详情 详情
(IV) 64905 2-methyl 1-(phenylmethyl) 5-oxo-4-(2-propenyl)-1,2-pyrrolidinedicarboxylate C17H19NO5 详情 详情
(V) 64906 2-methyl 1-(phenylmethyl) 5-hydroxy-4-(2-propenyl)-1,2-pyrrolidinedicarboxylate C17H21NO5 详情 详情
(VI) 64907 2-methyl 1-(phenylmethyl) 5-(acetyloxy)-4-(2-propenyl)-1,2-pyrrolidinedicarboxylate C19H23NO6 详情 详情
(VII) 40599 Allyltributyltin; Tributyl-2-propenylstannane 24850-33-7 C15H32Sn 详情 详情
(VIII) 64908 2-methyl 1-(phenylmethyl) 4,5-di(2-propenyl)-1,2-pyrrolidinedicarboxylate C20H25NO4 详情 详情
(IX) 64909 2-methyl 1-(phenylmethyl) 2,3,3a,4,7,7a-hexahydro-1H-indole-1,2-dicarboxylate C18H21NO4 详情 详情
(X) 64910 4-methyl 3-(phenylmethyl) octahydro-3H-oxireno[2,3-f]indole-3,4-dicarboxylate C18H21NO5 详情 详情
(XI) 64911 2-methyl 1-(phenylmethyl) 5,6-dihydroxyoctahydro-1H-indole-1,2-dicarboxylate C18H23NO6 详情 详情
(XII) 64912 2-methyl 1-(phenylmethyl) 5,6-bis{[(methyloxy)methyl]oxy}octahydro-1H-indole-1,2-dicarboxylate C22H31NO8 详情 详情
(XIII) 64913 methyl 5,6-bis{[(methyloxy)methyl]oxy}octahydro-1H-indole-2-carboxylate C14H25NO6 详情 详情
Extended Information