(2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-4,5-O-isopropylidenedioxy-6-heptene-1,2-diol

Base Information

Chemical Name:(2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-4,5-O-isopropylidenedioxy-6-heptene-1,2-diol
CAS No.:870862-50-3
Molecular Formula:C₂₈H₄₀O₆Si
Molecular Weight:500.707
Hs Code.:

Synonyms:(2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-4,5-O-isopropylidenedioxy-6-heptene-1,2-diol

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Chemical Property of (2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-4,5-O-isopropylidenedioxy-6-heptene-1,2-diol

Chemical Property:

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Technology Process of (2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-4,5-O-isopropylidenedioxy-6-heptene-1,2-diol

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

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

: 870862-50-3
(2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-4,5-O-isopropylidenedioxy-6-heptene-1,2-diol

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 97 percent / toluene / 2 h / 105 °C

2.1: 97 percent / NaH / various solvent(s); tetrahydrofuran / 4 h / 0 °C

3.1: 72 percent / acetic acid / H₂O / 4.5 h / 50 °C

With potassium tert-butylate; sodium hydride; acetic acid; In tetrahydrofuran; water; toluene; 1.2: Wittig reaction;
DOI:10.1021/jo051686m

Reference yield:

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

: 870862-50-3
(2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-4,5-O-isopropylidenedioxy-6-heptene-1,2-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 97 percent / NaH / various solvent(s); tetrahydrofuran / 4 h / 0 °C

2: 72 percent / acetic acid / H₂O / 4.5 h / 50 °C

With sodium hydride; acetic acid; In tetrahydrofuran; water;
DOI:10.1021/jo051686m

Reference yield:

: 1779-49-3
Methyltriphenylphosphonium bromide

: 870862-50-3
(2R,3R,4S,5S)-5-(tert-butyldiphenylsilanyloxymethyl)-4,5-O-isopropylidenedioxy-6-heptene-1,2-diol

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 97 percent / toluene / 2 h / 105 °C

2.1: 97 percent / NaH / various solvent(s); tetrahydrofuran / 4 h / 0 °C

3.1: 72 percent / acetic acid / H₂O / 4.5 h / 50 °C

With potassium tert-butylate; sodium hydride; acetic acid; In tetrahydrofuran; water; toluene; 1.2: Wittig reaction;
DOI:10.1021/jo051686m