(2R,3R,4R)-6-Benzenesulfonyl-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran

Base Information

• Chemical Name: (2R,3R,4R)-6-Benzenesulfonyl-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran
• CAS No.: 150949-13-6
• Molecular Formula: C₃₁H₅₀O₆SSi₂
• Molecular Weight: 606.971
• Mol file: 150949-13-6.mol

Synonyms:

Chemical Property of (2R,3R,4R)-6-Benzenesulfonyl-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R)-6-Benzenesulfonyl-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran

There total 3 articles about (2R,3R,4R)-6-Benzenesulfonyl-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-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:

(2R,3R,4R)-3-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-6-phenylsulfanyl-tetrahydro-pyran → (2R,3R,4R)-6-Benzenesulfonyl-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran (150949-13-6)

Guidance literature:

With magnesium monoperoxyphthalate hexahydrate; Yield given;

DOI:10.1016/S0040-4039(00)79162-3

Reference yield:

4-O-benzyl-1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose (111830-58-1) → (2R,3R,4R)-6-Benzenesulfonyl-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran (150949-13-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) HCl, 2.) i-Pr₂EtN

2: magnesium monoperoxyphthalate (MMPP)

With hydrogenchloride; magnesium monoperoxyphthalate hexahydrate; N-ethyl-N,N-diisopropylamine;

DOI:10.1016/S0040-4039(00)79162-3

Reference yield:

thiophenol (108-98-5) → (2R,3R,4R)-6-Benzenesulfonyl-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran (150949-13-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) HCl, 2.) i-Pr₂EtN

2: magnesium monoperoxyphthalate (MMPP)

With hydrogenchloride; magnesium monoperoxyphthalate hexahydrate; N-ethyl-N,N-diisopropylamine;

DOI:10.1016/S0040-4039(00)79162-3

upstream raw materials:

4-O-benzyl-1,2-dideoxy-3,6-di-O-tert-butyldimethylsilyl-2-deoxy-D-arabino-1-hexenopyranose

thiophenol

Downstream raw materials:

[(2R,3R,4R)-6-Benzenesulfonyl-3-benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-pyran-2-yl]-methanol

(4R,5R,6R)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-2-carboxylic acid methyl ester

((2R,3R,4R)-6-Benzenesulfonyl-3-benzyloxy-2-methyl-tetrahydro-pyran-4-yloxy)-tert-butyl-dimethyl-silane

(4R,5R,6R)-5-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-2-methoxy-6-methyl-tetrahydro-pyran-2-carboxylic acid methyl ester