(4S,5R)-5-((R)-1-(tert-butyl(dimethyl)silyloxy)ethyl)-4-((p-toluenesulfonyloxy)methyl)-2,2-dimethyl-1,3-dioxolane

Base Information

• Chemical Name: (4S,5R)-5-((R)-1-(tert-butyl(dimethyl)silyloxy)ethyl)-4-((p-toluenesulfonyloxy)methyl)-2,2-dimethyl-1,3-dioxolane
• CAS No.: 909767-44-8
• Molecular Formula: C₂₁H₃₆O₆SSi
• Molecular Weight: 444.665
• Mol file: 909767-44-8.mol

Synonyms:(4S,5R)-5-((R)-1-(tert-butyl(dimethyl)silyloxy)ethyl)-4-((p-toluenesulfonyloxy)methyl)-2,2-dimethyl-1,3-dioxolane

Chemical Property of (4S,5R)-5-((R)-1-(tert-butyl(dimethyl)silyloxy)ethyl)-4-((p-toluenesulfonyloxy)methyl)-2,2-dimethyl-1,3-dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-5-((R)-1-(tert-butyl(dimethyl)silyloxy)ethyl)-4-((p-toluenesulfonyloxy)methyl)-2,2-dimethyl-1,3-dioxolane

There total 5 articles about (4S,5R)-5-((R)-1-(tert-butyl(dimethyl)silyloxy)ethyl)-4-((p-toluenesulfonyloxy)methyl)-2,2-dimethyl-1,3-dioxolane 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: 92.0%

(4S,5R)-5-((R)-1-(tert-butyl(dimethyl)silyloxy)ethyl)-4-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane (909767-43-7) + p-toluenesulfonyl chloride (98-59-9) → (4S,5R)-5-((R)-1-(tert-butyl(dimethyl)silyloxy)ethyl)-4-((p-toluenesulfonyloxy)methyl)-2,2-dimethyl-1,3-dioxolane (909767-44-8)

Guidance literature:

With dmap; In dichloromethane; at 20 ℃; for 5h;

DOI:10.1016/j.tet.2006.06.053

Reference yield:

(4R,5S)-5-((R)-1-Hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methoxy-methyl-amide (929539-86-6) → (4S,5R)-5-((R)-1-(tert-butyl(dimethyl)silyloxy)ethyl)-4-((p-toluenesulfonyloxy)methyl)-2,2-dimethyl-1,3-dioxolane (909767-44-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 0.17 g / imidazole; DMAP / dimethylformamide / 2 h / 80 °C

2: 98 percent / NaBH₄; MeOH / 2 h / 0 - 20 °C

3: 92 percent / DMAP / CH₂Cl₂ / 5 h / 20 °C

With 1H-imidazole; methanol; dmap; sodium tetrahydroborate; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tet.2006.06.053

Reference yield:

(4R,5R)-5-((R)-1-(tert-butyl(dimethyl)silyloxy)ethyl)-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide (909767-42-6) → (4S,5R)-5-((R)-1-(tert-butyl(dimethyl)silyloxy)ethyl)-4-((p-toluenesulfonyloxy)methyl)-2,2-dimethyl-1,3-dioxolane (909767-44-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / NaBH₄; MeOH / 2 h / 0 - 20 °C

2: 92 percent / DMAP / CH₂Cl₂ / 5 h / 20 °C

With methanol; dmap; sodium tetrahydroborate; In dichloromethane;

DOI:10.1016/j.tet.2006.06.053

upstream raw materials:

(4S,5R)-5-((R)-1-(tert-butyl(dimethyl)silyloxy)ethyl)-4-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolane

p-toluenesulfonyl chloride

(4R,5S)-5-((R)-1-Hydroxy-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid methoxy-methyl-amide

(4R,5R)-5-((R)-1-(tert-butyl(dimethyl)silyloxy)ethyl)-N-methoxy-N,2,2-trimethyl-1,3-dioxolane-4-carboxamide