6-O-benzoyl-1,2-O-(1-methylethylidene)-5-O-[(4-methylphenyl)sulfonyl]hexofuranose

Base Information

• Chemical Name: 6-O-benzoyl-1,2-O-(1-methylethylidene)-5-O-[(4-methylphenyl)sulfonyl]hexofuranose
• CAS No.: 16749-44-3
• Molecular Formula: C23H26 O9 S
• Molecular Weight: 478.52
• Mol file: 16749-44-3.mol

Synonyms:Glucofuranose,1,2-O-isopropylidene-, 6-benzoate 5-p-toluenesulfonate (6CI); Glucofuranose,1,2-O-isopropylidene-, 6-benzoate 5-p-toluenesulfonate, a-D- (8CI);Furo[2,3-d]-1,3-dioxole, a-D-glucofuranose deriv.;6-O-Benzoyl-1,2-O-isopropylidene-5-O-p-tolylsulfonyl-a-D-glucofuranose; NSC 23612

Chemical Property of 6-O-benzoyl-1,2-O-(1-methylethylidene)-5-O-[(4-methylphenyl)sulfonyl]hexofuranose

Chemical Property:

• Vapor Pressure: 1.41E-17mmHg at 25°C
• Boiling Point: 646.1°Cat760mmHg
• Flash Point: 344.6°C
• Density: 1.335g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-O-benzoyl-1,2-O-(1-methylethylidene)-5-O-[(4-methylphenyl)sulfonyl]hexofuranose

There total 5 articles about 6-O-benzoyl-1,2-O-(1-methylethylidene)-5-O-[(4-methylphenyl)sulfonyl]hexofuranose 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: 86.1%

Benzoic acid (R)-2-[(3aR,5S,6S,6aR)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(toluene-4-sulfonyloxy)-ethyl ester (82529-84-8) → O6-benzoyl-O1,O2-isopropylidene-O5-(toluene-4-sulfonyl)-α-D-glucofuranose (16749-44-3)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; for 2h; Ambient temperature;

DOI:10.1016/S0040-4039(00)86974-9

Reference yield: 86.0%

Benzoic acid 2-[(3aR,5S,6S,6aR)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(toluene-4-sulfonyloxy)-ethyl ester (82529-84-8) → 4-methoxy-benzaldehyde (123-11-5) + Benzoic acid 2-((3aR,5S,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2-(toluene-4-sulfonyloxy)-ethyl ester (16749-44-3)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; for 2h; Ambient temperature;

DOI:10.1016/S0040-4020(01)90593-9

Reference yield:

6-O-benzoyl-1,2-O-isopropylidene-α-D-glucofuranose (3254-32-8) + p-toluenesulfonyl chloride (98-59-9) → O6-benzoyl-O1,O2-isopropylidene-O5-(toluene-4-sulfonyl)-α-D-glucofuranose (16749-44-3)

Guidance literature:

With pyridine; dichloromethane;

DOI:10.1021/jo01105a048

upstream raw materials:

6-O-benzoyl-1,2-O-isopropylidene-α-D-glucofuranose

p-toluenesulfonyl chloride

Benzoic acid (R)-2-[(3aR,5S,6S,6aR)-6-(4-methoxy-benzyloxy)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl]-2-(toluene-4-sulfonyloxy)-ethyl ester

3-O-benzoyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

O³,O⁵-diacetyl-O⁶-benzoyl-O¹,O²-isopropylidene-β-L-idofuranose

O³-acetyl-O⁶-benzoyl-O¹,O²-isopropylidene-O⁵-(toluene-4-sulfonyl)-α-D-glucofuranose

O³,O⁶-dibenzoyl-O¹,O²-isopropylidene-O⁵-(toluene-4-sulfonyl)-α-D-glucofuranose

1,2-O-isopropylidene-5-deoxy-α-D-glucofuranose