(2S,3S,4R,5S)-1-hydroxy-2,3-epoxy-2-methyl-4,5-O-isopropylidene-6-benzyloxy-4,5-hexanediol

Base Information

Chemical Name:(2S,3S,4R,5S)-1-hydroxy-2,3-epoxy-2-methyl-4,5-O-isopropylidene-6-benzyloxy-4,5-hexanediol
CAS No.:320343-43-9
Molecular Formula:C₁₇H₂₄O₅
Molecular Weight:308.375
Hs Code.:

Synonyms:(2S,3S,4R,5S)-1-hydroxy-2,3-epoxy-2-methyl-4,5-O-isopropylidene-6-benzyloxy-4,5-hexanediol

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Chemical Property of (2S,3S,4R,5S)-1-hydroxy-2,3-epoxy-2-methyl-4,5-O-isopropylidene-6-benzyloxy-4,5-hexanediol

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Technology Process of (2S,3S,4R,5S)-1-hydroxy-2,3-epoxy-2-methyl-4,5-O-isopropylidene-6-benzyloxy-4,5-hexanediol

There total 4 articles about (2S,3S,4R,5S)-1-hydroxy-2,3-epoxy-2-methyl-4,5-O-isopropylidene-6-benzyloxy-4,5-hexanediol 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%

: 320343-42-8
(2E,4S,5S)-1-hydroxy-2-methyl-4,5-O-isopropylidene-6-(benzyloxy)hex-2-ene-4,5-diol

: 320343-43-9
(2S,3S,4R,5S)-1-hydroxy-2,3-epoxy-2-methyl-4,5-O-isopropylidene-6-benzyloxy-4,5-hexanediol

: (2R,3R,4R,5S)-1-hydroxy-2,3-epoxy-2-methyl-4,5-O-isopropylidene-6-benzyloxy-4,5-hexanediol

Guidance literature:: With tert.-butylhydroperoxide; 4 Angstroem MS; titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; In dichloromethane; at -20 ℃; for 24h;
DOI:10.1021/jo005612g

Reference yield:

: 78469-77-9,81076-11-1,128820-40-6,78513-03-8
(4S,5S)-4-benzyloxymethyl-5-hydroxymethyl-2,2-dimethyl-1,3-dioxolane

: 320343-43-9
(2S,3S,4R,5S)-1-hydroxy-2,3-epoxy-2-methyl-4,5-O-isopropylidene-6-benzyloxy-4,5-hexanediol

Guidance literature:: Multi-step reaction with 4 steps

1: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / -78 - 0 °C

2: 1.12 g / CH₂Cl₂ / 0.5 h / 0 °C

3: 90 percent / DIBAL-H / CH₂Cl₂; hexane / 2.5 h / -78 °C

4: m-CPBA

With oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; In hexane; dichloromethane; 1: Swern oxidation / 2: Wittig reaction;
DOI:10.1021/jo005612g

Reference yield:

: 81028-12-8
(4S,5R)-4-benzyloxymethyl-2,2-dimethyl-1,3-dioxolane-5-carboxaldehyde

: 320343-43-9
(2S,3S,4R,5S)-1-hydroxy-2,3-epoxy-2-methyl-4,5-O-isopropylidene-6-benzyloxy-4,5-hexanediol

Guidance literature:: Multi-step reaction with 3 steps

1: 1.12 g / CH₂Cl₂ / 0.5 h / 0 °C

2: 90 percent / DIBAL-H / CH₂Cl₂; hexane / 2.5 h / -78 °C

3: m-CPBA

With diisobutylaluminium hydride; 3-chloro-benzenecarboperoxoic acid; In hexane; dichloromethane; 1: Wittig reaction;
DOI:10.1021/jo005612g