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【结 构 式】

【分子编号】55496

【品名】tert-butyl(diphenyl)silyl (2E,4Z)-5-(trimethylstannyl)-2,4-pentadienyl ether; tert-butyl(diphenyl){[(2E,4Z)-5-(trimethylstannyl)-2,4-pentadienyl]oxy}silane

【CA登记号】

【 分 子 式 】C24H34OSiSn

【 分 子 量 】485.32886

【元素组成】C 59.4% H 7.06% O 3.3% Si 5.79% Sn 24.46%

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:(XXI)

The selective deprotection of the Pmb- group of (XVIII) with DDQ in dichloromethane gives the secondary alcohol (XIX), which is submitted to a highly selective diimide reduction of its ethynylene group by means of 2-nitrobenzenesulfonyl hydrazide (NBSH) in THF/iPr-OH to yield the cis-iodovinyl compound (XX). The condensation of the iodovinyl compound (XX) with tributylstannane (XXI) by means of PdCl2(acetonitrile)2 in DMF affords the adduct (XXII), which is treated with PCl3/pyridine and then oxidized with tBu-OOH and Pmb-OH to provide the phosphate ester (XXIII). Finally, this compound is deprotected with HF/pyridine in acetonitrile to give the target fostriecin.

1 Jacobsen, E.N.; Chavez, D.E.; Total synthesis of fostriecin (CI-920). Angew Chem. Int Ed 2001, 40, 19, 3667.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XVIII) 55492 (6R)-6-{(E,3R,4R,6R)-6-{[tert-butyl(dimethyl)silyl]oxy}-8-iodo-4-[(4-methoxybenzyl)oxy]-3-methyl-3-[(triethylsilyl)oxy]-1-octen-7-ynyl}-5,6-dihydro-2H-pyran-2-one C34H53IO6Si2 详情 详情
(XIX) 55494 (6R)-6-{(E,3R,4R,6R)-6-{[tert-butyl(dimethyl)silyl]oxy}-4-hydroxy-8-iodo-3-methyl-3-[(triethylsilyl)oxy]-1-octen-7-ynyl}-5,6-dihydro-2H-pyran-2-one C26H45IO5Si2 详情 详情
(XX) 55495 (6R)-6-{(1E,3R,4R,6R,7Z)-6-{[tert-butyl(dimethyl)silyl]oxy}-4-hydroxy-8-iodo-3-methyl-3-[(triethylsilyl)oxy]-1,7-octadienyl}-5,6-dihydro-2H-pyran-2-one C26H47IO5Si2 详情 详情
(XXI) 55496 tert-butyl(diphenyl)silyl (2E,4Z)-5-(trimethylstannyl)-2,4-pentadienyl ether; tert-butyl(diphenyl){[(2E,4Z)-5-(trimethylstannyl)-2,4-pentadienyl]oxy}silane C24H34OSiSn 详情 详情
(XXII) 55497 (6R)-6-{(1E,3R,4R,6R,7Z,9Z,11E)-6-{[tert-butyl(dimethyl)silyl]oxy}-13-{[tert-butyl(diphenyl)silyl]oxy}-4-hydroxy-3-methyl-3-[(triethylsilyl)oxy]-1,7,9,11-tridecatetraenyl}-5,6-dihydro-2H-pyran-2-one C47H72O6Si3 详情 详情
(XXIII) 55498 (1R,3R,4Z,6Z,8E)-3-{[tert-butyl(dimethyl)silyl]oxy}-10-{[tert-butyl(diphenyl)silyl]oxy}-1-{(1R,2E)-1-methyl-3-[(2R)-6-oxo-3,6-dihydro-2H-pyran-2-yl]-1-[(triethylsilyl)oxy]-2-propenyl}-4,6,8-decatrienyl bis(4-methoxybenzyl) phosphate C63H89O11PSi3 详情 详情
Extended Information