(R)-1-Phenyl-ethanesulfonic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Base Information

• Chemical Name: (R)-1-Phenyl-ethanesulfonic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester
• CAS No.: 424839-30-5
• Molecular Formula: C₂₀H₂₈O₈S
• Molecular Weight: 428.504
• Mol file: 424839-30-5.mol

Synonyms:(R)-1-Phenyl-ethanesulfonic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

Chemical Property of (R)-1-Phenyl-ethanesulfonic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-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 (R)-1-Phenyl-ethanesulfonic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

There total 4 articles about (R)-1-Phenyl-ethanesulfonic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-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:

Phenyl-methanesulfonic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (412021-12-6) → (R)-1-Phenyl-ethanesulfonic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (424839-30-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 24h;

DOI:10.1002/1521-3773(20020104)41:1<109::AID-ANIE109>3.0.CO;2-F

Reference yield:

Phenyl-methanesulfonic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (412021-12-6) + methyl iodide (74-88-4) → (S)-1-Phenyl-ethanesulfonic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester + (R)-1-Phenyl-ethanesulfonic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (424839-30-5)

Guidance literature:

Phenyl-methanesulfonic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester; With n-butyllithium; In tetrahydrofuran; hexane; at -95 - -90 ℃; for 1h;

methyl iodide; In tetrahydrofuran; hexane; at -95 - -78 ℃;

DOI:10.1016/j.tet.2005.01.046

Reference yield:

Diacetone D-glucose (2595-05-3) → (R)-1-Phenyl-ethanesulfonic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester (424839-30-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 91 percent / Et₃N / CH₂Cl₂ / 24 h / 20 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -95 - -90 °C

2.2: tetrahydrofuran; hexane / -95 - -78 °C

With n-butyllithium; triethylamine; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1016/j.tet.2005.01.046

upstream raw materials:

Phenyl-methanesulfonic acid (3aR,5R,6R,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

methyl iodide

Diacetone D-glucose

benzenesulfonyl chloride

Downstream raw materials:

(R)-1-phenylethanesulfonic acid