• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】51730

【品名】[(3R,4S,6S,9aS)-3-(methoxymethoxy)-6-[(phenylsulfonyl)methyl]octahydro-2H-quinolizin-4-yl]methanol

【CA登记号】

【 分 子 式 】C19H29NO5S

【 分 子 量 】383.509

【元素组成】C 59.51% H 7.62% N 3.65% O 20.86% S 8.36%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(II)

The hydrolysis of the chiral isopropylidene ketal (I) with HCl in refluxing methanol, followed by selective monosilylation of the resulting primary OH group with tert-butyldiphenylsilyl chloride, protection of the secondary OH group with MOM-Cl and Hunig base, and desilylation with HF and pyridine gives the perhydroquinolizine-4-methanol derivative (II).The reaction of the OH group of (II) with I2 and PPh3¸, and deiodination of the resulting iodo derivative with Bu3SnH and AIBN yields the 4-methyl derivative (III), which is condensed with trans-2-nonenal and BuLi, and treated with Na/Hg to afford the 6-(1,3-decadienyl) derivative (IV). The deprotection of (IV) with HCl in refluxing methanol provides the secondary alcohol V), which is finally acetylated with acetic anhydride and pyridine to furnish the target (-)-clavepictine A.

1 Toyooka, N.; Nemoto, H.; Application of chiral building blocks to the synthesis of drugs. Drugs Fut 2002, 27, 2, 143.
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) 51729 (4aR,6aS,10S,11aS)-3,3-dimethyl-10-[(phenylsulfonyl)methyl]decahydro[1,3]dioxino[4,5-c]quinolizine; [(4aR,6aS,10S,11aS)-3,3-dimethyldecahydro[1,3]dioxino[4,5-c]quinolizin-10-yl]methyl phenyl sulfone C20H29NO4S 详情 详情
(II) 51730 [(3R,4S,6S,9aS)-3-(methoxymethoxy)-6-[(phenylsulfonyl)methyl]octahydro-2H-quinolizin-4-yl]methanol C19H29NO5S 详情 详情
(III) 51726 [(4S,6S,7R,9aS)-7-(methoxymethoxy)-6-methyloctahydro-2H-quinolizin-4-yl]methyl phenyl sulfone; (3R,4S,6S,9aS)-3-(methoxymethoxy)-4-methyl-6-[(phenylsulfonyl)methyl]octahydro-2H-quinolizine C19H29NO4S 详情 详情
(IV) 51731 (3R,4S,6S,9aS)-6-[(1E,3E)-1,3-decadienyl]-4-methyloctahydro-2H-quinolizin-3-yl methoxymethyl ether; (3R,4S,6S,9aS)-6-[(1E,3E)-1,3-decadienyl]-3-(methoxymethoxy)-4-methyloctahydro-2H-quinolizine C22H39NO2 详情 详情
(V) 51732 (3R,4S,6S,9aS)-6-[(1E,3E)-1,3-decadienyl]-4-methyloctahydro-2H-quinolizin-3-ol C20H35NO 详情 详情

合成路线2

该中间体在本合成路线中的序号:(II)

The hydrolysis of the chiral isopropylidene ketal (I) with HCl in refluxing methanol, followed by selective monosilylation of the resulting primary OH group with tert-butyldiphenylsilyl chloride, protection of the secondary OH group with MOM-Cl and Hunig base, and desilylation with HF and pyridine gives the perhydroquinolizine-4-methanol derivative (II).The reaction of the OH group of (II) with I2 and PPh3, and deiodination of the resulting iodo derivative with Bu3SnH and AIBN yields the 4-methyl derivative (III), which is condensed with trans-2-nonenal and BuLi, and treated with Na/Hg to afford the 6-(1,3-decadienyl) derivative (IV).Finally the deprotection of (IV) with HCl in refluxing methanol provides the target (+)-clavepictine B.

1 Toyooka, N.; Nemoto, H.; Application of chiral building blocks to the synthesis of drugs. Drugs Fut 2002, 27, 2, 143.
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) 51729 (4aR,6aS,10S,11aS)-3,3-dimethyl-10-[(phenylsulfonyl)methyl]decahydro[1,3]dioxino[4,5-c]quinolizine; [(4aR,6aS,10S,11aS)-3,3-dimethyldecahydro[1,3]dioxino[4,5-c]quinolizin-10-yl]methyl phenyl sulfone C20H29NO4S 详情 详情
(II) 51730 [(3R,4S,6S,9aS)-3-(methoxymethoxy)-6-[(phenylsulfonyl)methyl]octahydro-2H-quinolizin-4-yl]methanol C19H29NO5S 详情 详情
(III) 51726 [(4S,6S,7R,9aS)-7-(methoxymethoxy)-6-methyloctahydro-2H-quinolizin-4-yl]methyl phenyl sulfone; (3R,4S,6S,9aS)-3-(methoxymethoxy)-4-methyl-6-[(phenylsulfonyl)methyl]octahydro-2H-quinolizine C19H29NO4S 详情 详情
(IV) 51731 (3R,4S,6S,9aS)-6-[(1E,3E)-1,3-decadienyl]-4-methyloctahydro-2H-quinolizin-3-yl methoxymethyl ether; (3R,4S,6S,9aS)-6-[(1E,3E)-1,3-decadienyl]-3-(methoxymethoxy)-4-methyloctahydro-2H-quinolizine C22H39NO2 详情 详情
Extended Information