((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-yl)-methanol

Base Information

• Chemical Name: ((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-yl)-methanol
• CAS No.: 676241-03-5
• Molecular Formula: C₂₉H₃₂O₅
• Molecular Weight: 460.57
• Mol file: 676241-03-5.mol

Synonyms:((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-yl)-methanol

Chemical Property of ((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-yl)-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-yl)-methanol

There total 2 articles about ((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-yl)-methanol 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: 66.0%

Acetic acid (2R,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-ylmethyl ester (676241-01-3) → ((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-yl)-methanol (676241-03-5)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃; for 20h;

DOI:10.1016/j.tetlet.2003.12.032

Reference yield:

(2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-vinyltetrahydro-2H-pyran (112219-66-6) → ((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-yl)-methanol (676241-03-5)

Guidance literature:

Multi-step reaction with 2 steps

1: TMOTf / CH₂Cl₂ / 1.5 h / -40 °C

2: NaOMe / methanol / 2 h / pH 9

With sodium methylate; In methanol; dichloromethane;

DOI:10.1002/1099-0690(200103)2001:6<1053::aid-ejoc1053>3.3.co;2-j

Reference yield: 58.0%

((2R,3R,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-yl)-methanol (676241-03-5) + tert-butyl alcohol (75-65-0) → (2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-carboxylic acid tert-butyl ester (676241-04-6)

Guidance literature:

With acetic anhydride; pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1016/j.tetlet.2003.12.032

upstream raw materials:

Acetic acid (2R,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-ylmethyl ester

(2R,3R,4R,5S,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-vinyltetrahydro-2H-pyran

Downstream raw materials:

Toluene-4-sulfonic acid (2R,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-ylmethyl ester

(2S,3S,4R,5S,6S)-3,4,5-Tris-benzyloxy-6-vinyl-tetrahydro-pyran-2-carboxylic acid tert-butyl ester

(2R,3R,4S,5R,6R)-6-(azidomethyl)-3,4,5-tris(benzyloxy)-tetrahydro-2H-pyran-2-carboxylic acid

(2R,3R,4R,5S,6S)-2-Azidomethyl-3,4,5-tris-benzyloxy-6-vinyl-tetrahydro-pyran