(1R,2S,1'S)-1-benzyloxymethyl-1-fluoro-2-(1,2-O-isopropylidene-1,2-dihydroxyethyl)cyclopropane

Base Information

Chemical Name:(1R,2S,1'S)-1-benzyloxymethyl-1-fluoro-2-(1,2-O-isopropylidene-1,2-dihydroxyethyl)cyclopropane
CAS No.:147410-58-0
Molecular Formula:C₁₆H₂₁FO₃
Molecular Weight:280.339
Hs Code.:

Synonyms:(1R,2S,1'S)-1-benzyloxymethyl-1-fluoro-2-(1,2-O-isopropylidene-1,2-dihydroxyethyl)cyclopropane

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Chemical Property of (1R,2S,1'S)-1-benzyloxymethyl-1-fluoro-2-(1,2-O-isopropylidene-1,2-dihydroxyethyl)cyclopropane

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Technology Process of (1R,2S,1'S)-1-benzyloxymethyl-1-fluoro-2-(1,2-O-isopropylidene-1,2-dihydroxyethyl)cyclopropane

There total 7 articles about (1R,2S,1'S)-1-benzyloxymethyl-1-fluoro-2-(1,2-O-isopropylidene-1,2-dihydroxyethyl)cyclopropane 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: 59.0%

: 75-11-6
diiodomethane

: (S,E)-4-(3-(benzyloxy)-2-fluoroprop-1-en-1-yl)-2,2-dimethyl-1,3-dioxolane

: 147410-58-0
(1R,2S,1'S)-1-benzyloxymethyl-1-fluoro-2-(1,2-O-isopropylidene-1,2-dihydroxyethyl)cyclopropane

Guidance literature:: diiodomethane; With diethylzinc; trifluoroacetic acid; In hexane; dichloromethane; at 0 ℃; for 0.75h;

(S,E)-4-(3-(benzyloxy)-2-fluoroprop-1-en-1-yl)-2,2-dimethyl-1,3-dioxolane; In hexane; dichloromethane; at 0 - 15 ℃; for 15.8333h; diastereoselective reaction;
DOI:10.1021/jo502712g

Reference yield: 50.0%

: 75-11-6
diiodomethane

: (S)-4-((Z)-3-Benzyloxy-2-fluoro-propenyl)-2,2-dimethyl-[1,3]dioxolane

: 147410-58-0
(1R,2S,1'S)-1-benzyloxymethyl-1-fluoro-2-(1,2-O-isopropylidene-1,2-dihydroxyethyl)cyclopropane

Guidance literature:: With diethylzinc; In hexane; at 0 ℃; for 84h;
DOI:10.1248/cpb.40.3189

Reference yield:

: 15186-48-8
2,3-isopropylidene-glyceraldehyde

: 147410-58-0
(1R,2S,1'S)-1-benzyloxymethyl-1-fluoro-2-(1,2-O-isopropylidene-1,2-dihydroxyethyl)cyclopropane

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C, 1 h

2: 98 percent / DIBAL-H / diethyl ether; hexane / 2 h / 78 °C

3: 85 percent / NaH

4: 50 percent / Et₂Zn / hexane / 84 h / 0 °C

With diethylzinc; sodium hexamethyldisilazane; sodium hydride; diisobutylaluminium hydride; In diethyl ether; hexane;
DOI:10.1248/cpb.40.3189