(E)-(1S,2S)-1-Benzyloxymethoxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,5-dimethoxy-hex-3-en-2-ol

Base Information

Chemical Name:(E)-(1S,2S)-1-Benzyloxymethoxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,5-dimethoxy-hex-3-en-2-ol
CAS No.:104732-02-7
Molecular Formula:C₂₁H₃₂O₇
Molecular Weight:396.481
Hs Code.:

Synonyms:(E)-(1S,2S)-1-Benzyloxymethoxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,5-dimethoxy-hex-3-en-2-ol

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Chemical Property of (E)-(1S,2S)-1-Benzyloxymethoxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,5-dimethoxy-hex-3-en-2-ol

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Technology Process of (E)-(1S,2S)-1-Benzyloxymethoxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,5-dimethoxy-hex-3-en-2-ol

There total 16 articles about (E)-(1S,2S)-1-Benzyloxymethoxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,5-dimethoxy-hex-3-en-2-ol 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: 97.0%

: 107941-12-8
E-(2R,3R)-3-O-(benzyloxymethylene)-1,2-O-isopropylidene-5-octene-4,7-dione-1,2,3-triol, 7-dimethyl ketal

: 104732-02-7
(E)-(1S,2S)-1-Benzyloxymethoxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,5-dimethoxy-hex-3-en-2-ol

Guidance literature:: With zinc(II) tetrahydroborate; In diethyl ether; at -20 ℃; for 0.5h;
DOI:10.1021/ja00247a025

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 104732-02-7
(E)-(1S,2S)-1-Benzyloxymethoxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,5-dimethoxy-hex-3-en-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / diisopropylethylamine / CH₂Cl₂ / 24 h / Ambient temperature

2: 80 percent / pyridine, bromine / acetonitrile; H₂O / 1.) -20 deg C 2.) rt, 2 h

3: 92 percent / camphorsulfonic acid / methanol / 0 °C

4: 97 percent / Zn(BH₄)2 / diethyl ether / 0.5 h / -20 °C

With pyridine; zinc(II) tetrahydroborate; camphor-10-sulfonic acid; bromine; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; dichloromethane; water; acetonitrile;
DOI:10.1021/ja00247a025

Reference yield:

: 103061-82-1
(2R,3R)-1,2-O-isopropylidene-3-<2-(5-methylfuryl)>-1,2,3-propanetriol

: 104732-02-7
(E)-(1S,2S)-1-Benzyloxymethoxy-1-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-5,5-dimethoxy-hex-3-en-2-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 90 percent / diisopropylethylamine / CH₂Cl₂ / 24 h / Ambient temperature

2: 80 percent / pyridine, bromine / acetonitrile; H₂O / 1.) -20 deg C 2.) rt, 2 h

3: 92 percent / camphorsulfonic acid / methanol / 0 °C

4: 97 percent / Zn(BH₄)2 / diethyl ether / 0.5 h / -20 °C

With pyridine; zinc(II) tetrahydroborate; camphor-10-sulfonic acid; bromine; N-ethyl-N,N-diisopropylamine; In methanol; diethyl ether; dichloromethane; water; acetonitrile;
DOI:10.1021/ja00247a025