(4-tert-Butyl-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

Base Information

• Chemical Name: (4-tert-Butyl-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
• CAS No.: 412021-21-7
• Molecular Formula: C₂₃H₃₄O₈S
• Molecular Weight: 470.584
• Mol file: 412021-21-7.mol

Synonyms:(4-tert-Butyl-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

Chemical Property of (4-tert-Butyl-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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4-tert-Butyl-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

There total 1 articles about (4-tert-Butyl-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 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: 97.0%

Diacetone D-glucose (2595-05-3) + (4-tert-butylphenyl)methanesulfonyl chloride (519056-61-2) → (4-tert-Butyl-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 (412021-21-7)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃; for 24h;

DOI:10.1016/j.tet.2005.01.046

Reference yield: 53.0%

(E)-diethyl 1-ethoxycarbonyl-2-(4-methoxyphenyl)-vinylphosphonate (53235-81-7) + (4-tert-Butyl-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 (412021-21-7) → C39H57O14PS

Guidance literature:

(4-tert-Butyl-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; Inert atmosphere;

(E)-diethyl 1-ethoxycarbonyl-2-(4-methoxyphenyl)-vinylphosphonate; In tetrahydrofuran; hexane; at -95 - -90 ℃; for 4h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetasy.2009.10.011

Reference yield: 51.0%

(E)-3-phenyl-2-(diethoxyphosphoryl)acrylic acid ethyl ester (53235-77-1) + (4-tert-Butyl-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 (412021-21-7) → C38H55O13PS

Guidance literature:

(4-tert-Butyl-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; Inert atmosphere;

(E)-3-phenyl-2-(diethoxyphosphoryl)acrylic acid ethyl ester; In tetrahydrofuran; hexane; at -95 - -90 ℃; for 4h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetasy.2009.10.011

upstream raw materials:

Diacetone D-glucose

(4-tert-butylphenyl)methanesulfonyl chloride

Downstream raw materials:

(R)-1-(4-tert-Butyl-phenyl)-2-naphthalen-2-yl-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-(4-tert-Butyl-phenyl)-2-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-(4-tert-Butyl-phenyl)-but-3-ene-1-sulfonic 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-(4-tert-Butyl-phenyl)-3-methyl-but-3-ene-1-sulfonic 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