(3S,5S)-6-Bromo-5<(tert-butyldimethylsilyl)oxy>-3-hydroxy-6-heptenoic acid (R)-1,2,2-triphenyl-2-hydroxyethyl ester

Base Information

Chemical Name:(3S,5S)-6-Bromo-5<(tert-butyldimethylsilyl)oxy>-3-hydroxy-6-heptenoic acid (R)-1,2,2-triphenyl-2-hydroxyethyl ester
CAS No.:147986-45-6
Molecular Formula:C₃₃H₄₁BrO₅Si
Molecular Weight:625.675
Hs Code.:

Synonyms:(3S,5S)-6-Bromo-5<(tert-butyldimethylsilyl)oxy>-3-hydroxy-6-heptenoic acid (R)-1,2,2-triphenyl-2-hydroxyethyl ester

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Chemical Property of (3S,5S)-6-Bromo-5<(tert-butyldimethylsilyl)oxy>-3-hydroxy-6-heptenoic acid (R)-1,2,2-triphenyl-2-hydroxyethyl ester

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Technology Process of (3S,5S)-6-Bromo-5<(tert-butyldimethylsilyl)oxy>-3-hydroxy-6-heptenoic acid (R)-1,2,2-triphenyl-2-hydroxyethyl ester

There total 5 articles about (3S,5S)-6-Bromo-5<(tert-butyldimethylsilyl)oxy>-3-hydroxy-6-heptenoic acid (R)-1,2,2-triphenyl-2-hydroxyethyl ester 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:

: 147986-44-5
(S)-4-Bromo-3-<(tert-butyldimethylsilyl)oxy>-4-penten-1-ol

: 147986-45-6
(3S,5S)-6-Bromo-5<(tert-butyldimethylsilyl)oxy>-3-hydroxy-6-heptenoic acid (R)-1,2,2-triphenyl-2-hydroxyethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 84 percent / PCC, Zeolite 3 Angstroem / CH₂Cl₂ / 1 h / Ambient temperature

2: 1) LDA, 2) MgBr₂ / 1) a) THF, - 78 deg C, b) - 78 to 0 deg C, 2) a) - 78 deg C, b) - 115 deg C

With Zeolite 3 Angstroem; pyridinium chlorochromate; magnesium bromide; lithium diisopropyl amide; In dichloromethane;
DOI:10.1021/jo00061a028

Reference yield:

: 147986-42-3
(S)-4-Bromo-3-hydroxy-4-pentenoic acid (S)-1,2,2-triphenyl-2-hydroxyethyl ester

: 147986-45-6
(3S,5S)-6-Bromo-5<(tert-butyldimethylsilyl)oxy>-3-hydroxy-6-heptenoic acid (R)-1,2,2-triphenyl-2-hydroxyethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 57 percent / imidazole / acetonitrile / 3 h / Ambient temperature

2: 89 percent / DIBAH / diethyl ether / 1 h / 0 °C

3: 84 percent / PCC, Zeolite 3 Angstroem / CH₂Cl₂ / 1 h / Ambient temperature

4: 1) LDA, 2) MgBr₂ / 1) a) THF, - 78 deg C, b) - 78 to 0 deg C, 2) a) - 78 deg C, b) - 115 deg C

With 1H-imidazole; Zeolite 3 Angstroem; diisobutylaluminium hydride; pyridinium chlorochromate; magnesium bromide; lithium diisopropyl amide; In diethyl ether; dichloromethane; acetonitrile;
DOI:10.1021/jo00061a028

Reference yield:

: (S)-4-Bromo-3-<(tret-butyldimethylsilyl)oxy>-4-pentenoic acid (S)-1,2,2-triphenyl-2-hydroxyethyl ester

: 147986-45-6
(3S,5S)-6-Bromo-5<(tert-butyldimethylsilyl)oxy>-3-hydroxy-6-heptenoic acid (R)-1,2,2-triphenyl-2-hydroxyethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 89 percent / DIBAH / diethyl ether / 1 h / 0 °C

2: 84 percent / PCC, Zeolite 3 Angstroem / CH₂Cl₂ / 1 h / Ambient temperature

3: 1) LDA, 2) MgBr₂ / 1) a) THF, - 78 deg C, b) - 78 to 0 deg C, 2) a) - 78 deg C, b) - 115 deg C

With Zeolite 3 Angstroem; diisobutylaluminium hydride; pyridinium chlorochromate; magnesium bromide; lithium diisopropyl amide; In diethyl ether; dichloromethane;
DOI:10.1021/jo00061a028