(2RS,4S)-4-[(3'R,4'R,7'R,8'R)-8'-(tert-butyldimethylsilyloxy)-3'-hydroxy-4',7'-epoxy-1'-icosynyl]-2-phenyl-1,3-dioxolane

Base Information

Chemical Name:(2RS,4S)-4-[(3'R,4'R,7'R,8'R)-8'-(tert-butyldimethylsilyloxy)-3'-hydroxy-4',7'-epoxy-1'-icosynyl]-2-phenyl-1,3-dioxolane
CAS No.:532384-79-5
Molecular Formula:C₃₅H₅₈O₅Si
Molecular Weight:586.928
Hs Code.:

Synonyms:(2RS,4S)-4-[(3'R,4'R,7'R,8'R)-8'-(tert-butyldimethylsilyloxy)-3'-hydroxy-4',7'-epoxy-1'-icosynyl]-2-phenyl-1,3-dioxolane

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Chemical Property of (2RS,4S)-4-[(3'R,4'R,7'R,8'R)-8'-(tert-butyldimethylsilyloxy)-3'-hydroxy-4',7'-epoxy-1'-icosynyl]-2-phenyl-1,3-dioxolane

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Technology Process of (2RS,4S)-4-[(3'R,4'R,7'R,8'R)-8'-(tert-butyldimethylsilyloxy)-3'-hydroxy-4',7'-epoxy-1'-icosynyl]-2-phenyl-1,3-dioxolane

There total 3 articles about (2RS,4S)-4-[(3'R,4'R,7'R,8'R)-8'-(tert-butyldimethylsilyloxy)-3'-hydroxy-4',7'-epoxy-1'-icosynyl]-2-phenyl-1,3-dioxolane 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%

: 163730-22-1
(2R,5R)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-tridecyl]-tetrahydro-furan-2-carbaldehyde

: (4S)-4-ethynyl-2-phenyl-1,3-dioxolane

: 532384-79-5
(2RS,4S)-4-[(3'R,4'R,7'R,8'R)-8'-(tert-butyldimethylsilyloxy)-3'-hydroxy-4',7'-epoxy-1'-icosynyl]-2-phenyl-1,3-dioxolane

Guidance literature:: With (-)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine; In toluene; at 20 ℃;
DOI:10.1021/ol034131r

Reference yield: 97.0%

: 163730-22-1
(2R,5R)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-tridecyl]-tetrahydro-furan-2-carbaldehyde

: (4S)-4-ethynyl-2-phenyl-1,3-dioxolane

: 532384-79-5
(2RS,4S)-4-[(3'R,4'R,7'R,8'R)-8'-(tert-butyldimethylsilyloxy)-3'-hydroxy-4',7'-epoxy-1'-icosynyl]-2-phenyl-1,3-dioxolane

: 532384-85-3
(2RS,4S)-4-[(3'S,4'R,7'R,8'R)-8'-(tert-butyldimethylsilyloxy)-3'-hydroxy-4',7'-epoxy-1'-icosynyl]-2-phenyl-1,3-dioxolane

Guidance literature:: (4S)-4-ethynyl-2-phenyl-1,3-dioxolane; With (-)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine; In toluene; at 20 ℃; for 0.25h;

(2R,5R)-5-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-tridecyl]-tetrahydro-furan-2-carbaldehyde; In toluene; at 20 ℃; for 19h;
DOI:10.1002/chem.200305459

Reference yield:

: 161615-41-4
(2R,5R)-2-<(1R)-1-<(tert-butyldimethylsilyl)oxy>tridecyl>-5-(1-hydroxymethyl)tetrahydrofuran

: 532384-79-5
(2RS,4S)-4-[(3'R,4'R,7'R,8'R)-8'-(tert-butyldimethylsilyloxy)-3'-hydroxy-4',7'-epoxy-1'-icosynyl]-2-phenyl-1,3-dioxolane

Guidance literature:: Multi-step reaction with 2 steps

1: 82 percent / Dess-Martin periodinane; pyridine / CH₂Cl₂ / 0 - 20 °C

2: 97 percent / (1R,2S)-N-methylephedrine; zinc trifluoromethanesulfonate; triethylamine / toluene / 20 °C

With pyridine; (-)-N-methylephedrine; zinc trifluoromethanesulfonate; Dess-Martin periodane; triethylamine; In dichloromethane; toluene; 1: Dess-Martin oxidation;
DOI:10.1021/ol034131r