(4S,5S)-4-[(E)-(R)-3-(tert-Butyl-diphenyl-silanyloxy)-but-1-enyl]-5-hydroxymethyl-dihydro-furan-2-one

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Chemical Name:(4S,5S)-4-[(E)-(R)-3-(tert-Butyl-diphenyl-silanyloxy)-but-1-enyl]-5-hydroxymethyl-dihydro-furan-2-one
CAS No.:162680-09-3
Molecular Formula:C₂₅H₃₂O₄Si
Molecular Weight:424.612
Hs Code.:

Synonyms:(4S,5S)-4-[(E)-(R)-3-(tert-Butyl-diphenyl-silanyloxy)-but-1-enyl]-5-hydroxymethyl-dihydro-furan-2-one

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Chemical Property of (4S,5S)-4-[(E)-(R)-3-(tert-Butyl-diphenyl-silanyloxy)-but-1-enyl]-5-hydroxymethyl-dihydro-furan-2-one

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Technology Process of (4S,5S)-4-[(E)-(R)-3-(tert-Butyl-diphenyl-silanyloxy)-but-1-enyl]-5-hydroxymethyl-dihydro-furan-2-one

There total 5 articles about (4S,5S)-4-[(E)-(R)-3-(tert-Butyl-diphenyl-silanyloxy)-but-1-enyl]-5-hydroxymethyl-dihydro-furan-2-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: 79.0%

: 162680-08-2
(E)-(3S,6R)-6-(tert-Butyl-diphenyl-silanyloxy)-3-((S)-2,2-dimethyl-[1,3]dioxolan-4-yl)-hept-4-enoic acid dimethylamide

: 162680-09-3
(4S,5S)-4-[(E)-(R)-3-(tert-Butyl-diphenyl-silanyloxy)-but-1-enyl]-5-hydroxymethyl-dihydro-furan-2-one

Guidance literature:: With acetic acid; at 60 ℃; for 48h;
DOI:10.3987/COM-94-S15

Reference yield:

: 58479-61-1
tert-butylchlorodiphenylsilane

: 162680-09-3
(4S,5S)-4-[(E)-(R)-3-(tert-Butyl-diphenyl-silanyloxy)-but-1-enyl]-5-hydroxymethyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / imidazole / dimethylformamide / 18 h / 50 °C

2: 97 percent / n-BuLi / diethyl ether / 7 h / -78 °C

3: 1.) LDA / 1.) Et₂O, -78 deg C, 2.) Et₂O, -78 deg C, 2 h

4: 1.) L-selectride / 1.) THF, -78 deg C, 16 h, 2.) toluene, 95 deg C, 6 h

5: 79 percent / 60percent aq. AcOH / 48 h / 60 °C

With 1H-imidazole; n-butyllithium; L-Selectride; acetic acid; lithium diisopropyl amide; In diethyl ether; N,N-dimethyl-formamide;
DOI:10.3987/COM-94-S15

Reference yield:

: 162582-61-8
(R)-2-(tert-Butyl-diphenyl-silanyloxy)-propionic acid isobutyl ester

: 162680-09-3
(4S,5S)-4-[(E)-(R)-3-(tert-Butyl-diphenyl-silanyloxy)-but-1-enyl]-5-hydroxymethyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / n-BuLi / diethyl ether / 7 h / -78 °C

2: 1.) LDA / 1.) Et₂O, -78 deg C, 2.) Et₂O, -78 deg C, 2 h

3: 1.) L-selectride / 1.) THF, -78 deg C, 16 h, 2.) toluene, 95 deg C, 6 h

4: 79 percent / 60percent aq. AcOH / 48 h / 60 °C

With n-butyllithium; L-Selectride; acetic acid; lithium diisopropyl amide; In diethyl ether;
DOI:10.3987/COM-94-S15