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【结 构 式】

【分子编号】42418

【品名】(3R,4R)-3-methyl-8-[(triisopropylsilyl)oxy]-1-octen-4-ol

【CA登记号】

【 分 子 式 】C18H38O2Si

【 分 子 量 】314.58402

【元素组成】C 68.73% H 12.18% O 10.17% Si 8.93%

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:(LVII)

Synthesis of intermediate (LXIII): The reaction of aldehyde (LVI) with (-)-diisopinocampheyl-(E)-crotyl boronate (DIPCB) in toluene gives the chiral alcohol (LVII), which is protected with Bn-Br and NaH, yielding the benzyl ether (LVIII).The oxidation of the terminal double bond of (LVIII) with OsO4 and NaIO4 in THF/methanol/water affords the aldehyde (LIX), which is treated with (R,R)-diisopropyl allyl boronate (DISAB) to provide the allylic alcohol (LX). The silylation of (LX) with Tips-OTf, followed by debenzylation with Li/NH3 gives the secondary alcohol (LXI). The oxidation of the terminal double bond of (LXI) with OsO4 and NaIO4, with simultaneous cyclization yields the dihydropyran derivative (LXII), which is finally iodinated with n-BuLi, Bu3Sn-Cl and N-iodosuccinimide (NIS) in THF to afford the desired iodinate dihydropyran intermediate (LXIII).

1 Hayward, M.M.; et al.; Total synthesis of altohyrtin A (spongistatin 1): Part 2. Angew Chem. Int Ed Engl 1998, 37, 1-2, 192.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(LVI) 42417 5-[(triisopropylsilyl)oxy]pentanal C14H30O2Si 详情 详情
(LVII) 42418 (3R,4R)-3-methyl-8-[(triisopropylsilyl)oxy]-1-octen-4-ol C18H38O2Si 详情 详情
(LVIII) 42419 [[(5R,6R)-5-(benzyloxy)-6-methyl-7-octenyl]oxy](triisopropyl)silane; benzyl (1R,2R)-2-methyl-1-[4-[(triisopropylsilyl)oxy]butyl]-3-butenyl ether C25H44O2Si 详情 详情
(LIX) 42420 (2S,3R)-3-(benzyloxy)-2-methyl-7-[(triisopropylsilyl)oxy]heptanal C24H42O3Si 详情 详情
(LX) 42421 (4S,5R,6R)-6-(benzyloxy)-5-methyl-10-[(triisopropylsilyl)oxy]-1-decen-4-ol C27H48O3Si 详情 详情
(LXI) 42422 benzyl (1R,2S,3S)-2-methyl-3-[(triisopropylsilyl)oxy]-1-[4-[(triisopropylsilyl)oxy]butyl]-5-hexenyl ether; (5S,6S,7R)-5-allyl-7-(benzyloxy)-3,3,13,13-tetraisopropyl-2,6,14-trimethyl-4,12-dioxa-3,13-disilapentadecane C36H68O3Si2 详情 详情
(LXII) 42423 triisopropyl(4-[(2R,3S,4R)-3-methyl-4-[(triisopropylsilyl)oxy]-3,4-dihydro-2H-pyran-2-yl]butoxy)silane; (2R,3S,4R)-3-methyl-2-[4-[(triisopropylsilyl)oxy]butyl]-3,4-dihydro-2H-pyran-4-yl triisopropylsilyl ether C28H58O3Si2 详情 详情
(LXIII) 42424 (4-[(2R,3S,4R)-6-iodo-3-methyl-4-[(triisopropylsilyl)oxy]-3,4-dihydro-2H-pyran-2-yl]butoxy)(triisopropyl)silane; (2R,3S,4R)-6-iodo-3-methyl-2-[4-[(triisopropylsilyl)oxy]butyl]-3,4-dihydro-2H-pyran-4-yl triisopropylsilyl ether C28H57IO3Si2 详情 详情
Extended Information