(2R,3S,4aR,6R,7R,8aS)-2-(hydroxymethyl)-6-(phenylsulfonylmethyl)octahydropyrano[3,2-b]pyran-3,7-diol benzylidene acetal

Base Information

• Chemical Name: (2R,3S,4aR,6R,7R,8aS)-2-(hydroxymethyl)-6-(phenylsulfonylmethyl)octahydropyrano[3,2-b]pyran-3,7-diol benzylidene acetal
• CAS No.: 1246760-20-2
• Molecular Formula: C₂₃H₂₆O₇S
• Molecular Weight: 446.521
• Mol file: 1246760-20-2.mol

Synonyms:(2R,3S,4aR,6R,7R,8aS)-2-(hydroxymethyl)-6-(phenylsulfonylmethyl)octahydropyrano[3,2-b]pyran-3,7-diol benzylidene acetal

Chemical Property of (2R,3S,4aR,6R,7R,8aS)-2-(hydroxymethyl)-6-(phenylsulfonylmethyl)octahydropyrano[3,2-b]pyran-3,7-diol benzylidene acetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4aR,6R,7R,8aS)-2-(hydroxymethyl)-6-(phenylsulfonylmethyl)octahydropyrano[3,2-b]pyran-3,7-diol benzylidene acetal

There total 1 articles about (2R,3S,4aR,6R,7R,8aS)-2-(hydroxymethyl)-6-(phenylsulfonylmethyl)octahydropyrano[3,2-b]pyran-3,7-diol benzylidene acetal 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: 99.0%

2-((2R,4aR,6S,7R,8aS)-2-phenyl-7-((E)-2-(phenylsulfonyl)vinyloxy)hexahydropyrano[3,2-d][1,3]dioxin-6-yl)acetaldehyde (1246760-19-9) → (2R,3S,4aR,6R,7R,8aS)-2-(hydroxymethyl)-6-(phenylsulfonylmethyl)octahydropyrano[3,2-b]pyran-3,7-diol benzylidene acetal (1246760-20-2)

Guidance literature:

With methanol; samarium diiodide; In tetrahydrofuran; at 0 ℃; stereoselective reaction;

DOI:10.1016/j.tetasy.2010.04.066

Reference yield: 100.0%

(2R,3S,4aR,6R,7R,8aS)-2-(hydroxymethyl)-6-(phenylsulfonylmethyl)octahydropyrano[3,2-b]pyran-3,7-diol benzylidene acetal (1246760-20-2) → (2R,4aS,6R,7S,8aR)-7-hydroxy-6-(hydroxymethyl)-2-(phenylsulfonylmethyl)hexahydropyrano[3,2-b]pyran-3(2H)-one benzylidene acetal (1246760-29-1)

Guidance literature:

(2R,3S,4aR,6R,7R,8aS)-2-(hydroxymethyl)-6-(phenylsulfonylmethyl)octahydropyrano[3,2-b]pyran-3,7-diol benzylidene acetal; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -78 ℃;

With triethylamine; In dichloromethane; at -78 ℃;

DOI:10.1016/j.tetasy.2010.04.066

Reference yield: 96.0%

(2R,3S,4aR,6R,7R,8aS)-2-(hydroxymethyl)-6-(phenylsulfonylmethyl)octahydropyrano[3,2-b]pyran-3,7-diol benzylidene acetal (1246760-20-2) + acetic anhydride (108-24-7) → (2R,3R,4aS,6R,7S,8aR)-7-hydroxy-6-(hydroxymethyl)-2-(phenylsulfonylmethyl)octahydropyrano[3,2-b]pyran-3-yl acetate benzylidene acetal (1246760-21-3)

Guidance literature:

With pyridine; at 20 ℃;

DOI:10.1016/j.tetasy.2010.04.066

upstream raw materials:

2-((2R,4aR,6S,7R,8aS)-2-phenyl-7-((E)-2-(phenylsulfonyl)vinyloxy)hexahydropyrano[3,2-d][1,3]dioxin-6-yl)acetaldehyde

Downstream raw materials:

(2R,4aS,6R,7S,8aR)-7-hydroxy-6-(hydroxymethyl)-2-(phenylsulfonylmethyl)hexahydropyrano[3,2-b]pyran-3(2H)-one benzylidene acetal

(2R,3R,4aS,6R,7S,8aR)-7-hydroxy-6-(hydroxymethyl)-2-(phenylsulfonylmethyl)octahydropyrano[3,2-b]pyran-3-yl acetate benzylidene acetal

(2R,3S,4aR,6R,7R,8aS)-7-(tert-butyldimethylsilyloxy)-2-(hydroxymethyl)-6-(phenylsulfonylmethyl)octahydropyrano[3,2-b]pyran-3-ol benzylidene acetal