Toluene-4-sulfonic acid (3aR,5R,6S,6aR)-5-((R)-2-tert-butoxy-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (3aR,5R,6S,6aR)-5-((R)-2-tert-butoxy-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
• CAS No.: 145125-27-5
• Molecular Formula: C₂₀H₃₀O₈S
• Molecular Weight: 430.519
• Mol file: 145125-27-5.mol

Synonyms:

Chemical Property of Toluene-4-sulfonic acid (3aR,5R,6S,6aR)-5-((R)-2-tert-butoxy-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (3aR,5R,6S,6aR)-5-((R)-2-tert-butoxy-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

There total 1 articles about Toluene-4-sulfonic acid (3aR,5R,6S,6aR)-5-((R)-2-tert-butoxy-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester 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: 98.0%

trimethylaluminum (75-24-1) + 1,2:5,6-di-O-isopropylidene-3-O-tosyl-α-D-glucofuranoside (3253-75-6) → Toluene-4-sulfonic acid (3aR,5R,6S,6aR)-5-((R)-2-tert-butoxy-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (145125-27-5)

Guidance literature:

In dichloromethane; Mechanism; 1) -78 deg C, 4 h, 2) r.t., 15 h; other ketals;

DOI:10.1016/S0040-4020(01)86582-0

Reference yield: 94.0%

acetic anhydride (108-24-7) + Toluene-4-sulfonic acid (3aR,5R,6S,6aR)-5-((R)-2-tert-butoxy-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (145125-27-5) → 5-acetyl-6-O-tert-butyl-1,2-O-isopropylidene-3-p-toluenesulfonyl-D-glucofuranose

Guidance literature:

With pyridine; 0,2,4-dichlorophenyl-0-methylisopropylamidothiophosphate; for 20h; Ambient temperature;

DOI:10.1016/S0040-4020(01)86582-0

Reference yield:

Toluene-4-sulfonic acid (3aR,5R,6S,6aR)-5-((R)-2-tert-butoxy-1-hydroxy-ethyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (145125-27-5) → Toluene-4-sulfonic acid (3aR,5S,6R,6aR)-5-(2-tert-butoxy-acetyl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; Yield given. Multistep reaction; 1) CH₂Cl₂, -78 deg C, 1 h, 2) CH₂Cl₂, -78 deg C;

DOI:10.1016/S0040-4020(01)86582-0

upstream raw materials:

trimethylaluminum

1,2:5,6-di-O-isopropylidene-3-O-tosyl-α-D-glucofuranoside