(2S,3S,5R,6R)-3-(tert-butyldimethylsilyloxymethyl)-2-(p-toluenesulfonyloxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane

Base Information

• Chemical Name: (2S,3S,5R,6R)-3-(tert-butyldimethylsilyloxymethyl)-2-(p-toluenesulfonyloxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane
• CAS No.: 1407508-13-7
• Molecular Formula: C₂₃H₄₀O₈SSi
• Molecular Weight: 504.717
• Mol file: 1407508-13-7.mol

Synonyms:(2S,3S,5R,6R)-3-(tert-butyldimethylsilyloxymethyl)-2-(p-toluenesulfonyloxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane

Chemical Property of (2S,3S,5R,6R)-3-(tert-butyldimethylsilyloxymethyl)-2-(p-toluenesulfonyloxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,5R,6R)-3-(tert-butyldimethylsilyloxymethyl)-2-(p-toluenesulfonyloxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane

There total 4 articles about (2S,3S,5R,6R)-3-(tert-butyldimethylsilyloxymethyl)-2-(p-toluenesulfonyloxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane 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%

p-toluenesulfonyl chloride (98-59-9) + (2S,3S,5R,6R)-3-tert-butyldimethylsilyloxymethyl-2-hydroxymethyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane (241811-68-7) → (2S,3S,5R,6R)-3-(tert-butyldimethylsilyloxymethyl)-2-(p-toluenesulfonyloxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane (1407508-13-7)

Guidance literature:

With pyridine; dmap; at 0 - 20 ℃; Inert atmosphere;

DOI:10.1016/j.tetasy.2012.08.008

Reference yield:

(2R,3R,5R,6R)-5,6-dimethoxy-5,6-dimethyl[1,4]dioxane-2,3-dicarboxylic acid dimethyl ester (181586-74-3) → (2S,3S,5R,6R)-3-(tert-butyldimethylsilyloxymethyl)-2-(p-toluenesulfonyloxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane (1407508-13-7)

Guidance literature:

Multi-step reaction with 3 steps

1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C

2: sodium hydride / tetrahydrofuran / 20 °C

3: dmap; pyridine / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; lithium aluminium tetrahydride; sodium hydride; In tetrahydrofuran;

DOI:10.1016/j.tetasy.2012.08.008

Reference yield:

(2S,3S,5R,6R)-2,3-bis(hydroxymethyl)-5,6-dimethoxy-5,6-dimethyl<1,4>dioxane (173371-55-6) → (2S,3S,5R,6R)-3-(tert-butyldimethylsilyloxymethyl)-2-(p-toluenesulfonyloxymethyl)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane (1407508-13-7)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / tetrahydrofuran / 20 °C

2: dmap; pyridine / 0 - 20 °C / Inert atmosphere

With pyridine; dmap; sodium hydride; In tetrahydrofuran;

DOI:10.1016/j.tetasy.2012.08.008

upstream raw materials:

(2R,3R,5R,6R)-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane-2,3-dicarbothioic acid di-S-ethyl ester

p-toluenesulfonyl chloride

(2S,3S,5R,6R)-3-tert-butyldimethylsilyloxymethyl-2-hydroxymethyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane

(2R,3R,5R,6R)-5,6-dimethoxy-5,6-dimethyl[1,4]dioxane-2,3-dicarboxylic acid dimethyl ester

Downstream raw materials:

C₂₉H₄₈N₂O₈Si

C₂₃H₃₄N₂O₈

C₂₃H₃₂N₂O₉