(2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-1,2:4,5-di-O-isopropylidenedioxy-6-hepten-3-ol

Base Information

Chemical Name:(2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-1,2:4,5-di-O-isopropylidenedioxy-6-hepten-3-ol
CAS No.:870862-48-9
Molecular Formula:C₃₀H₄₂O₆Si
Molecular Weight:526.745
Hs Code.:

Synonyms:(2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-1,2:4,5-di-O-isopropylidenedioxy-6-hepten-3-ol

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Chemical Property of (2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-1,2:4,5-di-O-isopropylidenedioxy-6-hepten-3-ol

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Technology Process of (2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-1,2:4,5-di-O-isopropylidenedioxy-6-hepten-3-ol

There total 2 articles about (2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-1,2:4,5-di-O-isopropylidenedioxy-6-hepten-3-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%

: 870862-47-8
(2S,3S,4R,5R)-2-C-(tert-butyldiphenylsilanyloxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose

: 1779-49-3
Methyltriphenylphosphonium bromide

: 870862-48-9
(2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-1,2:4,5-di-O-isopropylidenedioxy-6-hepten-3-ol

Guidance literature:: Methyltriphenylphosphonium bromide; With potassium tert-butylate; In toluene; at 105 ℃; for 1h;

(2S,3S,4R,5R)-2-C-(tert-butyldiphenylsilanyloxymethyl)-2,3:5,6-di-O-isopropylidene-D-mannofuranose; In toluene; at 105 ℃; for 2h;
DOI:10.1021/jo051686m

Reference yield:

: 91738-34-0
2-C-(hydroxymethyl)-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose

: 870862-48-9
(2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-1,2:4,5-di-O-isopropylidenedioxy-6-hepten-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1.1: 85 percent / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 21.5 h / 0 - 20 °C

2.1: potassium tert-butoxide / toluene / 1 h / 105 °C

2.2: 97 percent / toluene / 2 h / 105 °C

With dmap; potassium tert-butylate; triethylamine; In dichloromethane; toluene; 2.2: Wittig reaction;
DOI:10.1021/jo051686m