(5R,6R,7R,8R)-7-(aminomethyl)-8-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】35023

【品名】(5R,6R,7R,8R)-7-(aminomethyl)-8-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylic acid

【CA登记号】

【分子式】C₂₂H₂₅NO₈

【分子量】431.44244

【元素组成】C 61.25% H 5.84% N 3.25% O 29.67%

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：(LXXIV)

The reaction of benzocyclobutane derivative (LXX) with isocyanate (LXXI) by means of Ph3SnOAc gives the carbamate (LXXII), which is cyclized by a thermal treatment with LiOH yielding the tetracyclic carboxylic acid (LXXIII). The opening of the oxazinone ring of (LXXIII) in basic medium affords the tricyclic amino acid (LXXIV), which is finally cyclized to the target compound by reaction with sodium nitrite in acidic medium (pH = 4).

参考文献中间体

合成目标

【1】 Ward, R.S.; Synthesis of podophyllotoxin and related compounds. Synthesis 1992, 719.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(LXX)	35019	(5R,6S)-6-(3,4,5-trimethoxyphenyl)-5,6-dihydrocyclobuta[f][1,3]benzodioxol-5-yl acetate	C₂₀H₂₀O₇	详情	详情
(LXXI)	35020	methyl (E)-4-isocyanato-2-butenoate	C₆H₇NO₃	详情	详情
(LXXII)	35021	methyl (E)-4-[([[(5R,6S)-6-(3,4,5-trimethoxyphenyl)-5,6-dihydrocyclobuta[f][1,3]benzodioxol-5-yl]oxy]carbonyl)amino]-2-butenoate	C₂₄H₂₅NO₉	详情	详情
(LXXIII)	35022	(4aR,5R,6R,11bR)-2-oxo-6-(3,4,5-trimethoxyphenyl)-3,4,4a,5,6,11b-hexahydro-2H-[1,3]dioxolo[4',5':6,7]naphtho[2,1-e][1,3]oxazine-5-carboxylic acid	C₂₃H₂₃NO₉	详情	详情
(LXXIV)	35023	(5R,6R,7R,8R)-7-(aminomethyl)-8-hydroxy-5-(3,4,5-trimethoxyphenyl)-5,6,7,8-tetrahydronaphtho[2,3-d][1,3]dioxole-6-carboxylic acid	C₂₂H₂₅NO₈	详情	详情

Extended Information