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【结 构 式】

【分子编号】47780

【品名】myristic acid

【CA登记号】

【 分 子 式 】C14H28O2

【 分 子 量 】228.37512

【元素组成】C 73.63% H 12.36% O 14.01%

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:(XV)

Cyclization of 5(R)-hydroxy-L-lysine (VIII) by means of EDC and HOBt, followed by treatment of the resulting amino lactam (IX) with Boc2O, furnished the N-Boc aminolactam (X). The configuration of the (R)-secondary alcohol was inverted by Mitsunobu coupling with p-nitrobenzoic acid (XI) to produce the (S)-p-nitrobenzoate ester (XII). Methylation of the lactam N of (XII) yielded (XIII), and hydrolysis of the p-nitrobenzoate ester of (XIII) with LiOH afforded the (S)-hydroxy lactam (XIV). Esterification of (XIV) with myristic acid (XV) in the presence of EDC and DMAP produced the myristate ester (XVI). Treatment of (XVI) with trifluoroacetic acid removed the Boc protecting group to yield amine (XVII). This was then condensed with the intermediate lactone (VIII) in refluxing isopropanol to produce amide (XVIII). Finally, acetonide hydrolysis in (XVIII) employing trifluoroacetic acid generated the title compound.

1 Kinder, F.R. Jr.; et al.; Total synthesis of bengamides B and E. J Org Chem 2001, 66, 6, 2118.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 47773 (4R,4aR,7R,7aS)-7-methoxy-2,2-dimethyl-4-[(E)-3-methyl-1-butenyl]tetrahydro-6H-furo[3,2-d][1,3]dioxin-6-one C14H22O5 详情 详情
(VIII) 47774 (2S,5R)-2,6-diamino-5-hydroxyhexanoic acid C6H14N2O3 详情 详情
(IX) 47775 (3S,6R)-3-amino-6-hydroxy-2-azepanone C6H12N2O2 详情 详情
(X) 47776 tert-butyl (3S,6R)-6-hydroxy-2-oxoazepanylcarbamate C11H20N2O4 详情 详情
(XI) 18119 4-nitrobenzoic acid; p-nitrobenzoic acid 62-23-7 C7H5NO4 详情 详情
(XII) 47777 (3S,6S)-6-[(tert-butoxycarbonyl)amino]-7-oxoazepanyl 4-nitrobenzoate C18H23N3O7 详情 详情
(XIII) 47778 (3S,6S)-6-[(tert-butoxycarbonyl)amino]-1-methyl-7-oxoazepanyl 4-nitrobenzoate C19H25N3O7 详情 详情
(XIV) 47779 tert-butyl (3S,6S)-6-hydroxy-1-methyl-2-oxoazepanylcarbamate C12H22N2O4 详情 详情
(XV) 47780 myristic acid C14H28O2 详情 详情
(XVI) 47781 (3S,6S)-6-[(tert-butoxycarbonyl)amino]-1-methyl-7-oxoazepanyl myristate C26H48N2O5 详情 详情
(XVII) 47783 (3S,6S)-6-amino-1-methyl-7-oxoazepanyl myristate C21H40N2O3 详情 详情
(XVIII) 47782 (3S,6S)-6-[((2R)-2-[(4R,5R,6R)-5-hydroxy-2,2-dimethyl-6-[(E)-3-methyl-1-butenyl]-1,3-dioxan-4-yl]-2-methoxyethanoyl)amino]-1-methyl-7-oxoazepanyl myristate C35H62N2O8 详情 详情
Extended Information