79330-96-4

Basic information

• Product Name: phenyl 2,3-di-O-benzoyl-6-O-benzyl-4-O-methylsulfonylethoxycarbonyl-1-thio-β-D-glucopyranoside
• Synonyms: phenyl 2,3-di-O-benzoyl-6-O-benzyl-4-O-methylsulfonylethoxycarbonyl-1-thio-β-D-glucopyranoside
• CAS NO: 79330-96-4
• Molecular Weight: 492.526
• Mol File: 79330-96-4.mol
• Article Data: 13

Chemical Properties

• CAS DataBase Reference: phenyl 2,3-di-O-benzoyl-6-O-benzyl-4-O-methylsulfonylethoxycarbonyl-1-thio-β-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: phenyl 2,3-di-O-benzoyl-6-O-benzyl-4-O-methylsulfonylethoxycarbonyl-1-thio-β-D-glucopyranoside(79330-96-4)
• EPA Substance Registry System: phenyl 2,3-di-O-benzoyl-6-O-benzyl-4-O-methylsulfonylethoxycarbonyl-1-thio-β-D-glucopyranoside(79330-96-4)

Safety Data

• Hazardous Substances Data: 79330-96-4(Hazardous Substances Data)

Upstream product

• 6748-91-0 methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 6748-85-2 methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 56253-32-8 methyl 4,6-O-benzylidene-β-D-glucopyranoside 2,3-di-O-benzoate 
• 100-39-0 benzyl bromide 
• 4137-35-3 methyl 2,3-di-O-benzoyl-α-D-glucopyranoside 

Downstream Products

• 1161358-25-3 C₆₂H₆₂O₁₃ 
• 1242007-92-6 methyl 2,3-di-O-benzoyl-6-O-benzyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-α-D-glucopyranosyl)-α-D-glucopyranoside 
• 1242007-95-9 methyl 2,3-di-O-benzoyl-6-O-benzyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-α-D-glucopyranoside 
• 1242007-83-5 methyl 2,3-di-O-benzoyl-6-O-benzyl-4-O-(3,4,6-tri-O-acetyl-2-deoxy-α-D-galactopyranosyl)-α-D-glucopyranoside 
• 145149-78-6 Methyl 2,3-di-O-benzoyl-6-O-benzyl-4-O-(imidazol-1-ylthiocarbonyl)-α-D-glucopyranoside 

Relevant articles and documents

The 2,2-Dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) Group: A Novel Protecting Group in Carbohydrate Chemistry

The 2,2-dimethyl-2-(ortho-nitrophenyl)acetyl (DMNPA) group was introduced to synthetic carbohydrate chemistry as a protecting group (PG) for the first time. Benefiting from a unique chemical structure and novel deprotection conditions, the DMNPA group can be cleaved rapidly and mutually orthogonal to other PGs. Orchestrated application of the DMNPA group with other PGs led to the highly efficient synthesis of the glycan of thornasterside A.

Method for preparing and removing saccharide hydroxyl protecting group dimethyl phenylacetyl DMNA

The invention relates to a method for preparing and removing saccharide hydroxyl protecting group dimethyl phenylacetyl DMNA. The method comprises the following steps: (1) efficiently introducing saccharide hydroxyl protecting group dimethyl phenylacetyl into saccharide hydroxyl; and (2) efficiently removing a hydroxyl protecting group shown in the description. The method is environmentally friendly and has the advantages that the advantages that the preparation is simple, the introduction is efficient, the operation is easy, the removal is efficient, and the application range is wide; and furthermore, a protecting group has very good stereoselectivity when being used for protecting 2-hydroxyl of a glycosyl donor, so that the development and application of the protecting group are promoted.

A practical approach to regioselective O-benzylation of primary positions of polyols

Exposure of saccharide polyols to a moderate excess of benzyl bromide and DIPEA at 90 °C results in the regioselective O-benzylation of primary positions in moderate to good yields. The reactions can be performed without inert atmosphere and provide synth