benzyl (2S,3S)-2-bromo-3-hydroxyhexanoate

Base Information

• Chemical Name: benzyl (2S,3S)-2-bromo-3-hydroxyhexanoate
• CAS No.: 428512-35-0
• Molecular Formula: C₁₃H₁₇BrO₃
• Molecular Weight: 301.18
• Mol file: 428512-35-0.mol

Synonyms:benzyl (2S,3S)-2-bromo-3-hydroxyhexanoate

Chemical Property of benzyl (2S,3S)-2-bromo-3-hydroxyhexanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl (2S,3S)-2-bromo-3-hydroxyhexanoate

There total 3 articles about benzyl (2S,3S)-2-bromo-3-hydroxyhexanoate 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: 80.0%

(4R,5S)-2,2-Dioxo-5-propyl-2λ6-[1,3,2]dioxathiolane-4-carboxylic acid benzyl ester (428512-29-2) → benzyl (2S,3S)-2-bromo-3-hydroxyhexanoate (428512-35-0)

Guidance literature:

(4R,5S)-2,2-Dioxo-5-propyl-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid benzyl ester; With lithium bromide; In tetrahydrofuran; at 20 ℃; for 12h;

With sulfuric acid; In diethyl ether; water; at 0 ℃; for 24h; Further stages.;

DOI:10.1021/jo011172x

Reference yield:

benzyl 2,3-dihydroxyhexanoate → benzyl (2S,3S)-2-bromo-3-hydroxyhexanoate (428512-35-0)

Guidance literature:

Multi-step reaction with 3 steps

1.1: SOCl₂; triethylamine / CH₂Cl₂ / 0.08 h / 0 °C

2.1: 3.64 g / NaIO₄ / RuCl₃ / acetonitrile; H₂O; CCl₄ / 1 h / 20 °C

3.1: LiBr / tetrahydrofuran / 12 h / 20 °C

3.2: 80 percent / H₂SO₄ / diethyl ether; H₂O / 24 h / 0 °C

With sodium periodate; thionyl chloride; triethylamine; lithium bromide; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; dichloromethane; water; acetonitrile;

DOI:10.1021/jo011172x

Reference yield:

2-oxo-5-propyl-2λ4-[1,3,2]dioxathiolane-4-carboxylic acid benzyl ester → benzyl (2S,3S)-2-bromo-3-hydroxyhexanoate (428512-35-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 3.64 g / NaIO₄ / RuCl₃ / acetonitrile; H₂O; CCl₄ / 1 h / 20 °C

2.1: LiBr / tetrahydrofuran / 12 h / 20 °C

2.2: 80 percent / H₂SO₄ / diethyl ether; H₂O / 24 h / 0 °C

With sodium periodate; lithium bromide; ruthenium trichloride; In tetrahydrofuran; tetrachloromethane; water; acetonitrile;

DOI:10.1021/jo011172x

upstream raw materials:

(4R,5S)-2,2-Dioxo-5-propyl-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid benzyl ester

Downstream raw materials:

benzyl (2R,3R)-N^α-(benzyloxycarbonyl)-3-propyl-aziridine-2-carboxylate

benzyl (2R,3R)-3-propyl-aziridine-2-carboxylate

benzyl (2R,3S)-2-azido-3-hydroxyhexanoate