tert-butyl (2R,3R,5S,6S)-6-[(E)-4-hydroxy-3-methyl-2-butenyl]-2,5-dimethyltetrahydro-2H-pyran-3-ylcarbamate -Drug Synthesis Database

【结构式】

【分子编号】62149

【品名】tert-butyl (2R,3R,5S,6S)-6-[(E)-4-hydroxy-3-methyl-2-butenyl]-2,5-dimethyltetrahydro-2H-pyran-3-ylcarbamate

【CA登记号】

【分子式】C₁₇H₃₁NO₄

【分子量】313.43748

【元素组成】C 65.14% H 9.97% N 4.47% O 20.42%

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：(XII)

Wittig reaction of aldehyde (X) with phosphorane (II) produces the unsaturated ester (XI), which is further reduced to the allylic alcohol (XII) with DIBAL in toluene. Treatment of (XII) with CBr4 and PPh3 leads to allyl bromide (XIII). This is then condensed with sodium p-toluenesulfinate (XIV), providing sulfone (XV). Subsequent acidic Boc group cleavage gives amine (XVI).

参考文献中间体

合成目标

【1】 Horigome, M.; Motoyoshi, H.; Watanabe, H.; Kitahara, T.; A synthesis of FR901464. Tetrahedron Lett 2001, 42, 46, 8207.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(II)	37071	ethyl 2-(triphenylphosphoranylidene)propanoate	5717-37-3	C₂₃H₂₃O₂P	详情	详情
(X)	62147	tert-butyl (2R,3R,5S,6S)-2,5-dimethyl-6-(2-oxoethyl)tetrahydro-2H-pyran-3-ylcarbamate		C₁₄H₂₅NO₄	详情	详情
(XI)	62148	ethyl (E)-4-{(2S,3S,5R,6R)-5-[(tert-butoxycarbonyl)amino]-3,6-dimethyltetrahydro-2H-pyran-2-yl}-2-methyl-2-butenoate		C₁₉H₃₃NO₅	详情	详情
(XII)	62149	tert-butyl (2R,3R,5S,6S)-6-[(E)-4-hydroxy-3-methyl-2-butenyl]-2,5-dimethyltetrahydro-2H-pyran-3-ylcarbamate		C₁₇H₃₁NO₄	详情	详情
(XIII)	62150	tert-butyl (2R,3R,5S,6S)-6-[(E)-4-bromo-3-methyl-2-butenyl]-2,5-dimethyltetrahydro-2H-pyran-3-ylcarbamate		C₁₇H₃₀BrNO₃	详情	详情
(XIV)	62151	4-methylbenzenesulfinate		C₇H₇O₂S	详情	详情
(XV)	62152	tert-butyl (2R,3R,5S,6S)-2,5-dimethyl-6-{(E)-3-methyl-4-[(4-methylphenyl)sulfonyl]-2-butenyl}tetrahydro-2H-pyran-3-ylcarbamate		C₂₄H₃₇NO₅S	详情	详情
(XVI)	62153	(2R,3R,5S,6S)-2,5-dimethyl-6-{(E)-3-methyl-4-[(4-methylphenyl)sulfonyl]-2-butenyl}tetrahydro-2H-pyran-3-amine; (2R,3R,5S,6S)-2,5-dimethyl-6-{(E)-3-methyl-4-[(4-methylphenyl)sulfonyl]-2-butenyl}tetrahydro-2H-pyran-3-ylamine		C₁₉H₂₉NO₃S	详情	详情

Extended Information