(+)-(3S,4R)-3-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-1-pentene

Base Information

• Chemical Name: (+)-(3S,4R)-3-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-1-pentene
• CAS No.: 108275-52-1
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.322
• Mol file: 108275-52-1.mol

Synonyms:(+)-(3S,4R)-3-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-1-pentene

Chemical Property of (+)-(3S,4R)-3-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-1-pentene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+)-(3S,4R)-3-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-1-pentene

There total 7 articles about (+)-(3S,4R)-3-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-1-pentene 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: 93.0%

(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-prop-2-en-1-ol (18524-19-1) + benzyl bromide (100-39-0) → (+)-(3S,4R)-3-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-1-pentene (108275-52-1)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 20 ℃; for 4h;

DOI:10.1016/j.tetasy.2009.03.039

Reference yield: 40.0%

(4R)-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)allyl alcohol (212579-64-1) + benzyl chloride (100-44-7) → (+)-(3S,4R)-3-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-1-pentene (108275-52-1)

Guidance literature:

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride;

DOI:10.1016/S0040-4039(00)80713-3

Reference yield:

2,3-isopropylidene-glyceraldehyde (15186-48-8) → (+)-(3S,4R)-3-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-1-pentene (108275-52-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / tetrahydrofuran / -20 °C

2: 40 percent / 50percent aq.NaOH / Et₃BnNCl

With sodium hydroxide; N-benzyl-N,N,N-triethylammonium chloride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)80713-3

upstream raw materials:

(4R)-1-(2,2-dimethyl-[1,3]dioxolan-4-yl)allyl alcohol

benzyl chloride

benzyl bromide

(1R,4'R)-1-(2,2-dimethyl-1,3-dioxolane-4-yl)-2-trimethylsilylprop-2-en-1-ol

Downstream raw materials:

(R)-2-(benzyloxy)-2-[(R)-2,2-dimethyl-1,3-dioxolan-4-yl]acetaldehyde

(2R,3S)-3-O-benzyl-4-pentene-1,2,3-triol

(2R/S,3S,4R)-3-benzyloxy-1,2-epoxy-4,5-O-isopropylidene-4,5-dihydroxypentane

(3S,4R)-1-bromo-3-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxypentane-2-one