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

Base Information

• Chemical Name: 2-O-[tert-butyl(dimethyl)silyl]-1,3-diedoxy-4,5-O-(1-methylethylidene)-6-O-[(4-methylphenyl)sulfonyl]-D-xylo-hexitol
• CAS No.: 1030835-95-0
• Molecular Formula: C₂₂H₃₈O₆SSi
• Molecular Weight: 458.692
• Mol file: 1030835-95-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about 2-O-[tert-butyl(dimethyl)silyl]-1,3-diedoxy-4,5-O-(1-methylethylidene)-6-O-[(4-methylphenyl)sulfonyl]-D-xylo-hexitol 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,5S)-5-[(R)-2-(tert-butyldimethylsilyloxy)propyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol (1031354-04-7) + p-toluenesulfonyl chloride (98-59-9) → 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)

Guidance literature:

{ (4S,5S)-5-[(R)-2-(tert-butyldimethylsilyloxy)propyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol; With dmap; triethylamine; In dichloromethane; at 20 ℃; for 0.166667h;

p-toluenesulfonyl chloride; In dichloromethane; at 320 ℃;

DOI:10.1055/s-0029-1218708

Reference yield:

tert-butyldimethyl(((2R)-1-(oxiran-2-yl)propan-2-yl)oxy)silane (866043-88-1) → 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)

Guidance literature:

Multi-step reaction with 8 steps

1.1: n-butyllithium / tetrahydrofuran / 0.67 h / -20 °C / Inert atmosphere

1.2: 3 h / -20 °C / Inert atmosphere

2.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-diisopropyl tartrate / decane; dichloromethane / 18.25 h / -20 °C / Inert atmosphere; Molecular sieve

3.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-diisopropyl tartrate / decane; dichloromethane / 192.25 h / -20 °C / Inert atmosphere; Molecular sieve

4.1: n-butyllithium / tetrahydrofuran / -20 °C / Inert atmosphere

4.2: 3 h / -20 °C / Inert atmosphere

5.1: pyridinium p-toluenesulfonate / acetone / 8 h / Inert atmosphere; Reflux

6.1: sodium periodate; osmium(VIII) oxide; water / diethyl ether / 24 h / 20 °C / Inert atmosphere; Saturated solution

7.1: sodium tetrahydroborate / methanol / 0.5 h / 20 °C / Inert atmosphere

8.1: dmap; triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; n-butyllithium; water; pyridinium p-toluenesulfonate; D-(-)-diisopropyl tartrate; triethylamine; In tetrahydrofuran; methanol; diethyl ether; decane; dichloromethane; acetone; 2.1: Sharpless asymmetric kinetic resolution / 3.1: Sharpless epoxidation;

DOI:10.1016/j.tetasy.2011.06.015

Reference yield:

(5R)-5-((tert-butyldimethylsilyl)oxy)hex-1-en-3-ol → 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)

Guidance literature:

Multi-step reaction with 7 steps

1.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-diisopropyl tartrate / decane; dichloromethane / 18.25 h / -20 °C / Inert atmosphere; Molecular sieve

2.1: titanium(IV) isopropylate; tert.-butylhydroperoxide; D-(-)-diisopropyl tartrate / decane; dichloromethane / 192.25 h / -20 °C / Inert atmosphere; Molecular sieve

3.1: n-butyllithium / tetrahydrofuran / -20 °C / Inert atmosphere

3.2: 3 h / -20 °C / Inert atmosphere

4.1: pyridinium p-toluenesulfonate / acetone / 8 h / Inert atmosphere; Reflux

5.1: sodium periodate; osmium(VIII) oxide; water / diethyl ether / 24 h / 20 °C / Inert atmosphere; Saturated solution

6.1: sodium tetrahydroborate / methanol / 0.5 h / 20 °C / Inert atmosphere

7.1: dmap; triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; n-butyllithium; water; pyridinium p-toluenesulfonate; D-(-)-diisopropyl tartrate; triethylamine; In tetrahydrofuran; methanol; diethyl ether; decane; dichloromethane; acetone; 1.1: Sharpless asymmetric kinetic resolution / 2.1: Sharpless epoxidation;

DOI:10.1016/j.tetasy.2011.06.015

upstream raw materials:

{ (4S,5S)-5-[(R)-2-(tert-butyldimethylsilyloxy)propyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methanol

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:

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