(8R,10S,12S)-8-[[(aminocarbonyl)oxy]methyl]-6-hydroxy-4-(hydroxymethyl)-14-oxa-1,11-diazatetracyclo[7.4.1.0(2,7).0(10,12)]tetradeca-2,4,6-trien-9-yl acetate -Drug Synthesis Database

【结构式】

【分子编号】47426

【品名】(8R,10S,12S)-8-[[(aminocarbonyl)oxy]methyl]-6-hydroxy-4-(hydroxymethyl)-14-oxa-1,11-diazatetracyclo[7.4.1.0(2,7).0(10,12)]tetradeca-2,4,6-trien-9-yl acetate

【CA登记号】

【分子式】C₁₆H₁₉N₃O₇

【分子量】365.34288

【元素组成】C 52.6% H 5.24% N 11.5% O 30.65%

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：(LVIII)

The reaction of (LV) with Ac2O and pyridine gives the acetate (LVI), which is detosylated with sodium naphthalenide in DME to yield compound (LVII). The hydrogenation of (LVII) with H2 over Pd/C in ethyl acetate eliminates the Bn and Bom protecting groups to afford dihydroxy compound (LVIII), which is oxidized at the carbinol group with oxalyl chloride to provide the aldehyde (LIX). Finally, the cleavage of the acetoxy group of (LIX) with ammonia in methanol furnishes the target compound.

参考文献中间体

合成目标

【1】 Katoh, T.; Terashima, S.; Total synthesis of antitumor antibiotic FR900482. Yuki Gosei Kagaku Kyokaishi 1997, 55, 11, 946.
【2】 Katoh, T.; et al.; Total synthesis of an enantiomeric pair of FR900482. 3. Completion of the synthesis by assembling the two segments. Tetrahedron 1997, 53, 30, 10253.
【3】 Katoh, T.; et al.; Total synthesis of natural (+)-FR900482. 3. Completion of the synthesis. Tetrahedron Lett 1996, 37, 20, 3479.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(LV)	47423	[(8R,9S,10S,12S)-6-(benzyloxy)-4-[[(benzyloxy)methoxy]methyl]-9-hydroxy-11-[(4-methylphenyl)sulfonyl]-14-oxa-1,11-diazatetracyclo[7.4.1.0(2,7).0(10,12)]tetradeca-2,4,6-trien-8-yl]methyl carbamate	C₃₆H₃₇N₃O₉S	详情	详情
(LVI)	47424	(8R,10S,12S)-8-[[(aminocarbonyl)oxy]methyl]-6-(benzyloxy)-4-[[(benzyloxy)methoxy]methyl]-11-[(4-methylphenyl)sulfonyl]-14-oxa-1,11-diazatetracyclo[7.4.1.0(2,7).0(10,12)]tetradeca-2,4,6-trien-9-yl acetate	C₃₈H₃₉N₃O₁₀S	详情	详情
(LVII)	47425	(8R,10S,12S)-8-[[(aminocarbonyl)oxy]methyl]-6-(benzyloxy)-4-[[(benzyloxy)methoxy]methyl]-14-oxa-1,11-diazatetracyclo[7.4.1.0(2,7).0(10,12)]tetradeca-2,4,6-trien-9-yl acetate	C₃₁H₃₃N₃O₈	详情	详情
(LVIII)	47426	(8R,10S,12S)-8-[[(aminocarbonyl)oxy]methyl]-6-hydroxy-4-(hydroxymethyl)-14-oxa-1,11-diazatetracyclo[7.4.1.0(2,7).0(10,12)]tetradeca-2,4,6-trien-9-yl acetate	C₁₆H₁₉N₃O₇	详情	详情
(LIX)	47427	(8R,10S,12S)-8-[[(aminocarbonyl)oxy]methyl]-4-formyl-6-hydroxy-14-oxa-1,11-diazatetracyclo[7.4.1.0(2,7).0(10,12)]tetradeca-2,4,6-trien-9-yl acetate	C₁₆H₁₇N₃O₇	详情	详情

Extended Information