ethyl (2R,3S)-5-benzyloxy-2,3-dihydroxypentanoate

Base Information

• Chemical Name: ethyl (2R,3S)-5-benzyloxy-2,3-dihydroxypentanoate
• CAS No.: 501648-78-8
• Molecular Formula: C₁₄H₂₀O₅
• Molecular Weight: 268.31
• Mol file: 501648-78-8.mol

Synonyms:ethyl (2R,3S)-5-benzyloxy-2,3-dihydroxypentanoate

Chemical Property of ethyl (2R,3S)-5-benzyloxy-2,3-dihydroxypentanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (2R,3S)-5-benzyloxy-2,3-dihydroxypentanoate

There total 3 articles about ethyl (2R,3S)-5-benzyloxy-2,3-dihydroxypentanoate 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: 73.0%

ethyl (2E)-5-(benzyloxy)pent-2-enoate (70542-83-5) → ethyl (2R,3S)-5-benzyloxy-2,3-dihydroxypentanoate (501648-78-8)

Guidance literature:

With AD-mix-α; methanesulfonamide; sodium hydrogencarbonate; In water; tert-butyl alcohol; at 0 ℃; for 24h;

DOI:10.1002/1522-2675(200210)85:10<3090::AID-HLCA3090>3.0.CO;2-8

Reference yield:

ethyl (2E)-5-(benzyloxy)pent-2-enoate (70542-83-5) → ethyl (2R,3S)-5-benzyloxy-2,3-dihydroxypentanoate (501648-78-8) + (2S,3R)-5-Benzyloxy-2,3-dihydroxy-pentanoic acid ethyl ester

Guidance literature:

With AD-mix-α; methanesulfonamide; In water; tert-butyl alcohol; at 4 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1016/S0040-4039(96)02121-1

Reference yield:

3-Benzyloxypropanal (19790-60-4) → ethyl (2R,3S)-5-benzyloxy-2,3-dihydroxypentanoate (501648-78-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / DBU, LiCl / acetonitrile

2: AD-mix α, MeSO2NH2 / 2-methyl-propan-2-ol; H2O / 4 °C

With AD-mix-α; methanesulfonamide; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; In water; acetonitrile; tert-butyl alcohol;

DOI:10.1016/S0040-4039(96)02121-1

upstream raw materials:

ethyl (2E)-5-(benzyloxy)pent-2-enoate

3-Benzyloxypropanal

Downstream raw materials:

4-{(1S,2S)-4-Benzyloxy-2-hydroxy-1-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylcarbamoyl]-butylcarbamoyl}-butyric acid benzyl ester

{(1S,2S)-4-Benzyloxy-2-hydroxy-1-[2-((2S,3R,4R,5R,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yl)-ethylcarbamoyl]-butyl}-carbamic acid tert-butyl ester

ethyl (2R,3S)-3-hydroxy-5-(4-nitrophenoxy)-2-[(2-nitrophenylsulfonyl)oxy]pentanoate

ethyl (4R,5S)-2,2-dimethyl-5-[2-(4-nitrophenoxy)ethyl]-1,3-dioxolane-4-carboxylate