2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE

Base Information

• Chemical Name: 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE
• CAS No.: 64768-20-3
• Molecular Formula: C34H28O10
• Molecular Weight: 596.59
• Hs Code.: 2932999099
• Mol file: 64768-20-3.mol

Synonyms:2,3,4,6-Tetra-O-benzoyl-b-D-glucopyranose;

Chemical Property of 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 151-156 °C
• Refractive Index: 1.645
• Boiling Point: 744.233 °C at 760 mmHg
• PKA: 11.20±0.70(Predicted)
• Flash Point: 237.752 °C
• PSA: 134.66000
• Density: 1.389 g/cm³
• LogP: 4.23740
• Storage Temp.: −20°C

Purity/Quality:

97% ^*data from raw suppliers

2,3,4,6-Tetra-O-benzoyl-β-D-glucopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2,3,4,6-Tetra-O-benzoyl-β-D-glucopyranose (CAS# 64768-20-3) is a useful chiral building block used in the synthetic preparation of saponins, and glycosides.

Technology Process of 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE

There total 25 articles about 2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSE 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: 67.0%

1,2,3,4,6-penta-O-benzoyl-α-D-mannopyranoside (2592-58-7,3006-48-2,3006-49-3,13526-09-5,14679-57-3,22415-91-4,29884-70-6,41545-55-5,41545-56-6,41569-33-9,96996-90-6,121570-85-2,121570-86-3) → 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside (64768-20-3,66530-18-5,113544-55-1,121530-16-3,121530-28-7,135216-27-2,101857-05-0)

Guidance literature:

With ethanolamine; In tetrahydrofuran; for 21h; Inert atmosphere;

DOI:10.1002/chem.201104069

Reference yield: 37.0%

2-(2'-phenylethynylphenyl)phenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside → C54H39IO10 + C20H13IO + 2,3,4,6-tetra-O-benzoyl-α-D-glucopyranose (66530-18-5) + 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranose (64768-20-3)

Guidance literature:

2-(2'-phenylethynylphenyl)phenyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside; With N-iodo-succinimide; In dichloromethane; at -25 ℃; for 0.0833333h; Inert atmosphere;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -25 ℃; for 12h; Inert atmosphere;

DOI:10.1021/jacs.9b00210

Reference yield:

1,2,3,4,6-penta-O-benzoyl-β-D-glucopyranose (2592-58-7,3006-48-2,3006-49-3,13526-09-5,14679-57-3,22415-91-4,29884-70-6,41545-55-5,41545-56-6,41569-33-9,96996-90-6,121570-85-2,121570-86-3) → 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranose (64768-20-3)

Guidance literature:

With methylamine; In tetrahydrofuran; Inert atmosphere;

DOI:10.1021/ol300808c

upstream raw materials:

1,2,3,4,6-penta-O-benzoyl-α-D-mannopyranoside

alpha-D-mannopyranoside

1,2,3,4,6-penta-O-benzoyl-β-D-mannopyranose

allyl α-D-mannopyranoside

Downstream raw materials:

triethylammonium 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl hydrogenphosphonate

2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl iodide

methyl 2,3,4-tri-O-benzoyl-6-O-(2,3,4,6-tetra-O-benzoyl-D-glucopyranosyl)-α-D-glucopyranoside

methyl 4-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-2,3,6-tri-O-benzyl-α-D-glucopyranoside