(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

Base Information

Chemical Name:(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
CAS No.:375826-94-1
Molecular Formula:C₂₄H₃₅NO₃S₂
Molecular Weight:449.679
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 7 articles about (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 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:

: 101979-45-7
(S)-3-acetyl-4-isopropyl-1,3-thiazolidine-2-thione

: 375826-93-0
(E)-(4S,5S)-5-Benzyloxy-4,6-dimethyl-hept-2-enal

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

: 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

Guidance literature:: With 1-ethyl-piperidine; tin(II) trifluoromethanesulfonate; In dichloromethane; at -50 ℃; Title compound not separated from byproducts;
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

: 375826-94-1
(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

Guidance literature:: Multi-step reaction with 4 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

With 1-ethyl-piperidine; 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

Reference yield:

: 375826-91-8
(2S,3S)-3-Benzyloxy-2,4-dimethyl-pentan-1-ol

: 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

Guidance literature:: Multi-step reaction with 5 steps

1.1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -60 - 20 °C

2.1: 2.40 g / acetonitrile / 18 h / 90 °C

3.1: 84 percent / DIBAL-H / diethyl ether; hexane / 1.25 h / -78 - 0 °C

4.1: 99 percent / IBX / dimethylsulfoxide / 2 h

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

5.2: CH₂Cl₂ / 14 h / -78 - -50 °C

With 1-ethyl-piperidine; tin(II) trifluoromethanesulfonate; oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In diethyl ether; hexane; dichloromethane; dimethyl sulfoxide; acetonitrile; 1.1: Swern oxidation / 2.1: Wittig olefination / 5.2: Nagao aldol reaction;
DOI:10.1016/S0040-4020(02)00666-X