((4S,5S)-5-((R)-2-hydroxypropyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate

Base Information

• Chemical Name: ((4S,5S)-5-((R)-2-hydroxypropyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate
• CAS No.: 1233961-23-3
• Molecular Formula: C₁₆H₂₄O₆S
• Molecular Weight: 344.429
• Mol file: 1233961-23-3.mol

Synonyms:((4S,5S)-5-((R)-2-hydroxypropyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate

Chemical Property of ((4S,5S)-5-((R)-2-hydroxypropyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ((4S,5S)-5-((R)-2-hydroxypropyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate

There total 31 articles about ((4S,5S)-5-((R)-2-hydroxypropyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate 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: 90.0%

2-O-[tert-butyl(dimethyl)silyl]-1,3-diedoxy-4,5-O-(1-methylethylidene)-6-O-[(4-methylphenyl)sulfonyl]-D-xylo-hexitol (1030835-95-0) + p-toluenesulfonyl chloride (98-59-9) → ((4S,5S)-5-((R)-2-hydroxypropyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate (1233961-23-3)

Guidance literature:

2-O-[tert-butyl(dimethyl)silyl]-1,3-diedoxy-4,5-O-(1-methylethylidene)-6-O-[(4-methylphenyl)sulfonyl]-D-xylo-hexitol; With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 0.166667h;

p-toluenesulfonyl chloride; In dichlomethane; at 20 ℃; for 3h;

DOI:10.1055/s-0029-1218708

Reference yield: 85.0%

5-O-[(tert-butyl)(diphenyl)silyl]-4,6-dideoxy-2,3-O-(1-methylethylidene)-1-O-[(4-methylphenyl)-sulfonyl]-D-xylohexitol → ((4S,5S)-5-((R)-2-hydroxypropyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate (1233961-23-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20 ℃; for 2h;

DOI:10.1002/hlca.201400086

Reference yield: 70.0%

(R)-1-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-propan-2-ol (1240380-51-1) + p-toluenesulfonyl chloride (98-59-9) → ((4S,5S)-5-((R)-2-hydroxypropyl)-2,2-dimethyl-1,3-dioxolan-4-yl)methyl 4-methylbenzenesulfonate (1233961-23-3)

Guidance literature:

(R)-1-((4S,5S)-2,2-dimethyl-5-vinyl-1,3-dioxolan-4-yl)-propan-2-ol; With dimethylsulfide; ozone; In dichloromethane; at -78 - 20 ℃; Inert atmosphere;

With sodium tetrahydroborate; In methanol; for 0.5h; Inert atmosphere;

p-toluenesulfonyl chloride; With sodium hydride; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

DOI:10.1002/ejoc.201600625

upstream raw materials:

2-O-[tert-butyl(dimethyl)silyl]-1,3-diedoxy-4,5-O-(1-methylethylidene)-6-O-[(4-methylphenyl)sulfonyl]-D-xylo-hexitol

p-toluenesulfonyl chloride

(2R)-1-(oxiran-2-yl)propan-2-ol

tert-butyldimethyl(((2R)-1-(oxiran-2-yl)propan-2-yl)oxy)silane

Downstream raw materials:

C₁₃H₁₆O₄