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

Base Information

• Chemical Name: (2R/S,3S,4R)-3-benzyloxy-1,2-epoxy-4,5-O-isopropylidene-4,5-dihydroxypentane
• CAS No.: 847380-71-6
• Molecular Formula: C₁₅H₂₀O₄
• Molecular Weight: 264.321

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

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

Chemical Property:

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

There total 3 articles about (2R/S,3S,4R)-3-benzyloxy-1,2-epoxy-4,5-O-isopropylidene-4,5-dihydroxypentane 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: 90.0%

(+)-(3S,4R)-3-benzyloxy-4,5-O-isopropylidene-4,5-dihydroxy-1-pentene (108275-52-1) → (2R/S,3S,4R)-3-benzyloxy-1,2-epoxy-4,5-O-isopropylidene-4,5-dihydroxypentane (847380-71-6)

Guidance literature:

With sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1055/s-2004-834907

Reference yield:

(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-prop-2-en-1-ol (18524-19-1) → (2R/S,3S,4R)-3-benzyloxy-1,2-epoxy-4,5-O-isopropylidene-4,5-dihydroxypentane (847380-71-6)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaH / dimethylformamide

1.2: 4 g / dimethylformamide / 16 h / 40 °C

2.1: 90 percent / NaHCO₃; mCPBA / CH₂Cl₂ / 24 h / 20 °C

With sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-2004-834907

Reference yield:

(2S,3S,4R)-1,2;3,4-di-O-isopropylidene-5-iodo-1,2,3,4-pentanetetrol (71769-39-6) → (2R/S,3S,4R)-3-benzyloxy-1,2-epoxy-4,5-O-isopropylidene-4,5-dihydroxypentane (847380-71-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Zn / ethanol / 0.75 h / Heating

2.1: NaH / dimethylformamide

2.2: 4 g / dimethylformamide / 16 h / 40 °C

3.1: 90 percent / NaHCO₃; mCPBA / CH₂Cl₂ / 24 h / 20 °C

With sodium hydride; sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid; zinc; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1055/s-2004-834907

upstream raw materials:

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

(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-prop-2-en-1-ol

(2S,3S,4R)-1,2;3,4-di-O-isopropylidene-5-iodo-1,2,3,4-pentanetetrol

Downstream raw materials:

(2R/S,3S,4R)-1-bromo-3-benzyloxy-4,5-O-isopropylidene-2,4,5-trihydroxypentane

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

2-amino-4-[(1'S,2'S)-3'-azido-1'-benzyloxy-2'-chloropropyl]thiazole N²-tert-butylcarbamate

2-amino-4-[(1'S,2'S)-3'-amino-1'-benzyloxy-2'-chloropropyl]thiazole N²-tert-butylcarbamate

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