(2S,3S,4R)-5-Benzyloxy-4-fluoro-2,3-dihydroxy-pentanoic acid ethyl ester

Base Information

• Chemical Name: (2S,3S,4R)-5-Benzyloxy-4-fluoro-2,3-dihydroxy-pentanoic acid ethyl ester
• CAS No.: 197389-33-6
• Molecular Formula: C₁₄H₁₉FO₅
• Molecular Weight: 286.3
• Mol file: 197389-33-6.mol

Synonyms:(2S,3S,4R)-5-Benzyloxy-4-fluoro-2,3-dihydroxy-pentanoic acid ethyl ester

Chemical Property of (2S,3S,4R)-5-Benzyloxy-4-fluoro-2,3-dihydroxy-pentanoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R)-5-Benzyloxy-4-fluoro-2,3-dihydroxy-pentanoic acid ethyl ester

There total 3 articles about (2S,3S,4R)-5-Benzyloxy-4-fluoro-2,3-dihydroxy-pentanoic acid ethyl 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: 96.0%

(E)-(S)-5-Benzyloxy-4-fluoro-pent-2-enoic acid ethyl ester (197389-31-4) → (2S,3S,4R)-5-Benzyloxy-4-fluoro-2,3-dihydroxy-pentanoic acid ethyl ester (197389-33-6)

Guidance literature:

With potassium osmate(VI); AD-mix-β; for 0.5h;

DOI:10.1021/jo9714829

Reference yield:

C26H47FO5Si2 → (2S,3S,4R)-5-Benzyloxy-4-fluoro-2,3-dihydroxy-pentanoic acid ethyl ester (197389-33-6)

Guidance literature:

With hydrogen fluoride; water; In water; acetonitrile; at 20 ℃; for 5h;

DOI:10.1002/chem.200800956

Reference yield:

3-Benzyloxy-2-fluoro-propionaldehyde → (2S,3S,4R)-5-Benzyloxy-4-fluoro-2,3-dihydroxy-pentanoic acid ethyl ester (197389-33-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 71 percent / NaH / tetrahydrofuran / -78 °C

2: 96 percent / AD-mix-β, K2OsO4*2H2O / 0.5 h

With potassium osmate(VI); AD-mix-β; sodium hydride; In tetrahydrofuran;

DOI:10.1021/jo9714829

upstream raw materials:

(E)-(S)-5-Benzyloxy-4-fluoro-pent-2-enoic acid ethyl ester

Downstream raw materials:

(4S,5S)-5-((R)-2-Benzyloxy-1-fluoro-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid ethyl ester