(2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dichloro-1-methyl-vinyloxy)-tetrahydro-pyran

Base Information

• Chemical Name: (2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dichloro-1-methyl-vinyloxy)-tetrahydro-pyran
• CAS No.: 660852-02-8
• Molecular Formula: C₃₇H₃₈Cl₂O₆
• Molecular Weight: 649.611
• Mol file: 660852-02-8.mol

Synonyms:(2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dichloro-1-methyl-vinyloxy)-tetrahydro-pyran

Chemical Property of (2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dichloro-1-methyl-vinyloxy)-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dichloro-1-methyl-vinyloxy)-tetrahydro-pyran

There total 2 articles about (2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dichloro-1-methyl-vinyloxy)-tetrahydro-pyran 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: 85.0%

benzyl bromide (100-39-0) + (2R,3S,4S,5S,6R)-2-(2,2-Dichloro-1-methyl-vinyloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (660852-01-7) → (2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dichloro-1-methyl-vinyloxy)-tetrahydro-pyran (660852-02-8)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 4h;

DOI:10.1055/s-2003-42487

Reference yield:

Acetic acid (2R,3R,4S,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(2,2-dichloro-1-methyl-vinyloxy)-tetrahydro-pyran-4-yl ester (660852-00-6) → (2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dichloro-1-methyl-vinyloxy)-tetrahydro-pyran (660852-02-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / NaOMe / methanol / 1 h

2: 85 percent / NaH / dimethylformamide / 4 h / 20 °C

With sodium methylate; sodium hydride; In methanol; N,N-dimethyl-formamide;

DOI:10.1055/s-2003-42487

Reference yield: 80.0%

(2R,3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dichloro-1-methyl-vinyloxy)-tetrahydro-pyran (660852-02-8) → 2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside (4132-28-9,4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,78609-16-2)

Guidance literature:

With trifluoroacetic acid; at 65 ℃; for 3h;

DOI:10.1055/s-2003-42487

upstream raw materials:

benzyl bromide

(2R,3S,4S,5S,6R)-2-(2,2-Dichloro-1-methyl-vinyloxy)-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Acetic acid (2R,3R,4S,5S,6R)-3,5-diacetoxy-2-acetoxymethyl-6-(2,2-dichloro-1-methyl-vinyloxy)-tetrahydro-pyran-4-yl ester

Downstream raw materials:

2,3,4,6-tetra-O-benzyl-α-D-mannopyranoside