(3S)-3-([(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-methylpentanoyl]oxy)-13-methyltetradecanoic acid -Drug Synthesis Database

【结构式】

【分子编号】31816

【品名】(3S)-3-([(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-methylpentanoyl]oxy)-13-methyltetradecanoic acid

【CA登记号】

【分子式】C₂₆H₄₉NO₆

【分子量】471.6782

【元素组成】C 66.21% H 10.47% N 2.97% O 20.35%

与该中间体有关的原料药合成路线共 2 条

合成路线1 合成路线2

合成路线1

该中间体在本合成路线中的序号：(IV),(V)

Condensation of (R)-benzyl 3-hydroxy-13-methyl tetradecanoate (I) with N-Boc-L-isoleucine (II) in the presence of dicyclohexyl carbodiimide and dimethylaminopyridine furnished the corresponding ester (III). After deprotection of the benzyl group of (III) by hydrogenation over Pd/C, the resulting carboxylic acid (IV) was attached to an oxime resin using O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU) to give the resin-coupled product (V).

参考文献中间体

合成目标

【1】 Yanai, M.; Suguroi, T.; Solid-phase synthesis of cyclooctadepsipeptide N-4909 using a cyclization-cleavage method with oxime resin. J Antibiot 1999, 52, 9, 835.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(IV),(V)	31816	(3S)-3-([(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-methylpentanoyl]oxy)-13-methyltetradecanoic acid		C₂₆H₄₉NO₆	详情	详情
(I)	31814	benzyl (3R)-3-hydroxy-13-methyltetradecanoate		C₂₂H₃₆O₃	详情	详情
(II)	30009	(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-methylpentanoic acid	13139-16-7	C₁₁H₂₁NO₄	详情	详情
(III)	31815	benzyl (3S)-3-([(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-methylpentanoyl]oxy)-13-methyltetradecanoate		C₃₃H₅₅NO₆	详情	详情

合成路线2

该中间体在本合成路线中的序号：(V)

Removal of the Boc protecting group of (V) with trifluoroacetic acid was followed by coupling with N-Boc-D-leucine (VI) in the presence of HATU to provide (VII). The deprotection-coupling procedure was repeated using N-Boc-L-aspartic acid gamma-benzyl ester (VIII), N-Boc-L-valine (X), and N-Boc-D-Leucine yielding the depsipeptide resins (IX), (XI) and (XII), respectively.

参考文献中间体

合成目标

【1】 Yanai, M.; Suguroi, T.; Solid-phase synthesis of cyclooctadepsipeptide N-4909 using a cyclization-cleavage method with oxime resin. J Antibiot 1999, 52, 9, 835.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(V)	31816	(3S)-3-([(2S,3S)-2-[(tert-butoxycarbonyl)amino]-3-methylpentanoyl]oxy)-13-methyltetradecanoic acid		C₂₆H₄₉NO₆	详情	详情
(VI)	31819	(2R)-2-[(tert-butoxycarbonyl)amino]-4-methylpentanoic acid	16937-99-8	C₁₁H₂₁NO₄	详情	详情
(VII)	31817	(6R,9S,12S)-6-isobutyl-2,2-dimethyl-9-[(1S)-1-methylpropyl]-12-(10-methylundecyl)-4,7,10-trioxo-3,11-dioxa-5,8-diazatetradecan-14-oic acid		C₃₂H₆₀N₂O₇	详情	详情
(VIII)	25219	(2S)-4-(benzyloxy)-2-[(tert-butoxycarbonyl)amino]-4-oxobutyric acid	7536-58-5	C₁₆H₂₁NO₆	详情	详情
(IX)	31821	(6S,9R,12S,15S)-6-[2-(benzyloxy)-2-oxoethyl]-9-isobutyl-2,2-dimethyl-12-[(1S)-1-methylpropyl]-15-(10-methylundecyl)-4,7,10,13-tetraoxo-3,14-dioxa-5,8,11-triazaheptadecan-17-oic acid		C₄₃H₇₁N₃O₁₀	详情	详情
(X)	19733	(2S)-2-[(tert-butoxycarbonyl)amino]-3-methylbutyric acid		C₁₀H₁₉NO₄	详情	详情
(XI)	31822	(6S,9S,12R,15S,18S)-9-[2-(benzyloxy)-2-oxoethyl]-12-isobutyl-6-isopropyl-2,2-dimethyl-15-[(1S)-1-methylpropyl]-18-(10-methylundecyl)-4,7,10,13,16-pentaoxo-3,17-dioxa-5,8,11,14-tetraazaicosan-20-oic acid		C₄₈H₈₀N₄O₁₁	详情	详情
(XII)	31823	(6S,9S,12S,15R,18S,21S)-12-[2-(benzyloxy)-2-oxoethyl]-6,15-diisobutyl-9-isopropyl-2,2-dimethyl-18-[(1S)-1-methylpropyl]-21-(10-methylundecyl)-4,7,10,13,16,19-hexaoxo-3,20-dioxa-5,8,11,14,17-pentaazatricosan-23-oic acid		C₅₄H₉₁N₅O₁₂	详情	详情

Extended Information