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【结 构 式】

【分子编号】63075

【品名】(4S)-3-hexyl-4-[(2R)-2-(tetrahydro-2H-pyran-2-yloxy)tridecyl]-2-oxetanone

【CA登记号】

【 分 子 式 】C27H50O4

【 分 子 量 】438.6916

【元素组成】C 73.92% H 11.49% O 14.59%

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:(LIV)

Oxetanone (XLV) can also be obtained as follows: The reaction of 3(R)-hydroxytetradecanoic acid tert-butyl ester (XLVI) with DHP and p-toluenesulfonic acid gives the corresponding tetrahydropyranyl ether (XLVII), which is reduced with dibutylaluminum hydride (DIBAL) in toluene to the aldehyde (XI), already obtained. Compound (XI) is condensed with 2-(p-toluenesulfinyl)acetic acid tert-butyl ester (XLVIII) by means of tert-butylmagnesium bromide in ether-THF affording the sulfinylhydroxy ester (II), which is treated with aluminum amalgam in THF-water to yield the hydroxy ester (L). The alkylation of (L) with hexyl bromide (LI) by means of butyllithium and diisopropylamine in THF-hexane affords 2-hexyl-3(S)-hydroxy-5(R)-(tetrahydropyranyloxy)hexadecanoic acid tert-butyl ester (LII), which is hydrolyzed with KOH in methanol to the corresponding free acid (LIII). The lactonization of (LIII) with pyridinium p-toluenesulfonate in hot ethanol affords oxetanone (LIV) as a diastereomeric mixture, which is separated by column chromatography, finally yielding oxetanone (XLV), previously obtained in scheme 11082301c.

1 Barbier, P.; Schneider, F.; Synthesis of tetrahydrolipstatin and tetrahydroesterastin, compounds with beta-lactone moiety. Stereoselective hydrogenation of a beta-keto delta-lactone and conversion of the delta-lactone into a beta-lactone. J Org Chem 1988, 53, 6, 1218-21.
2 Prous, J.; Mealy, N.; Castaner, J.; Orlistat. Drugs Fut 1994, 19, 11, 1003.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IL) 11106 tert-butyl (3S,5R)-3-hydroxy-2-[(4-methylphenyl)sulfinyl]-5-(tetrahydro-2H-pyran-2-yloxy)hexadecanoate C32H54O6S 详情 详情
(XLV) 11102 (3S,4S)-3-Hexyl-4-[(2R)-2-(tetrahydro-2H-pyran-2-yloxy)tridecyl]-2-oxetanone C27H50O4 详情 详情
(XLVI) 11103 tert-butyl (3R)-3-hydroxytetradecanoate C18H36O3 详情 详情
(XLVII) 11104 tert-butyl (3R)-3-(tetrahydro-2H-pyran-2-yloxy)tetradecanoate C23H44O4 详情 详情
(XLVIII) 11105 tert-butyl 2-[(4-methylphenyl)sulfinyl]acetate C13H18O3S 详情 详情
(L) 11107 tert-butyl (3S,5R)-3-hydroxy-5-(tetrahydro-2H-pyran-2-yloxy)hexadecanoate C25H48O5 详情 详情
(LI) 11108 n-Hexyl bromide; 1-Bromohexane 111-25-1 C6H13Br 详情 详情
(LII) 11109 tert-butyl (3S,5R)-2-hexyl-3-hydroxy-5-(tetrahydro-2H-pyran-2-yloxy)hexadecanoate C31H60O5 详情 详情
(LIII) 11110 (3S,5R)-2-Hexyl-3-hydroxy-5-(tetrahydro-2H-pyran-2-yloxy)hexadecanoic acid C27H52O5 详情 详情
(LIV) 63075 (4S)-3-hexyl-4-[(2R)-2-(tetrahydro-2H-pyran-2-yloxy)tridecyl]-2-oxetanone C27H50O4 详情 详情
Extended Information