(E)-(3R,6S,7S)-7-Benzyloxy-3-hydroxy-6,8-dimethyl-non-4-enoic acid methoxy-methyl-amide

Base Information

Chemical Name:(E)-(3R,6S,7S)-7-Benzyloxy-3-hydroxy-6,8-dimethyl-non-4-enoic acid methoxy-methyl-amide
CAS No.:375826-95-2
Molecular Formula:C₂₀H₃₁NO₄
Molecular Weight:349.47
Hs Code.:

Synonyms:(E)-(3R,6S,7S)-7-Benzyloxy-3-hydroxy-6,8-dimethyl-non-4-enoic acid methoxy-methyl-amide

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Chemical Property of (E)-(3R,6S,7S)-7-Benzyloxy-3-hydroxy-6,8-dimethyl-non-4-enoic acid methoxy-methyl-amide

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Technology Process of (E)-(3R,6S,7S)-7-Benzyloxy-3-hydroxy-6,8-dimethyl-non-4-enoic acid methoxy-methyl-amide

There total 9 articles about (E)-(3R,6S,7S)-7-Benzyloxy-3-hydroxy-6,8-dimethyl-non-4-enoic acid methoxy-methyl-amide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 375826-94-1
(E)-(3R,6S,7S)-7-Benzyloxy-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-6,8-dimethyl-non-4-en-1-one

: 76186-04-4
(S)-4-isopropylthiazolidine-2-thione

: 375826-95-2
(E)-(3R,6S,7S)-7-Benzyloxy-3-hydroxy-6,8-dimethyl-non-4-enoic acid methoxy-methyl-amide

Guidance literature:: With 1H-imidazole; In dichloromethane; for 18h;
DOI:10.1016/S0040-4020(02)00666-X

Reference yield: 90.0%

: 6638-79-5
N,O-dimethylhydroxylamine*hydrochloride

: 375826-94-1
(E)-(3R,6S,7S)-7-Benzyloxy-3-hydroxy-1-((S)-4-isopropyl-2-thioxo-thiazolidin-3-yl)-6,8-dimethyl-non-4-en-1-one

: 375826-95-2
(E)-(3R,6S,7S)-7-Benzyloxy-3-hydroxy-6,8-dimethyl-non-4-enoic acid methoxy-methyl-amide

Guidance literature:: With 1H-imidazole;
DOI:10.1002/1521-3773(20010903)40:17<3224::AID-ANIE3224>3.0.CO;2-D

Reference yield:

: 233681-54-4
(2R,3S)-3-benzyloxy-2,4-dimethylpentanal

: 375826-95-2
(E)-(3R,6S,7S)-7-Benzyloxy-3-hydroxy-6,8-dimethyl-non-4-enoic acid methoxy-methyl-amide

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2.40 g / acetonitrile / 18 h / 90 °C

2.1: 84 percent / DIBAL-H / diethyl ether; hexane / 1.25 h / -78 - 0 °C

3.1: 99 percent / IBX / dimethylsulfoxide / 2 h

4.1: Sn(OTf)2; N-ethylpiperidine / CH₂Cl₂ / 4 h / -50 °C

4.2: CH₂Cl₂ / 14 h / -78 - -50 °C

5.1: 95 percent / imidazole / CH₂Cl₂ / 18 h

With 1-ethyl-piperidine; 1H-imidazole; tin(II) trifluoromethanesulfonate; diisobutylaluminium hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile; 1.1: Wittig olefination / 4.2: Nagao aldol reaction;
DOI:10.1016/S0040-4020(02)00666-X