4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzyl-1,5-D-gluconolactone

Base Information

• Chemical Name: 4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzyl-1,5-D-gluconolactone
• CAS No.: 88970-25-6
• Molecular Formula: C₆₁H₆₂O₁₁
• Molecular Weight: 971.157
• Mol file: 88970-25-6.mol

Synonyms:4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzyl-1,5-D-gluconolactone

Chemical Property of 4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzyl-1,5-D-gluconolactone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzyl-1,5-D-gluconolactone

There total 8 articles about 4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzyl-1,5-D-gluconolactone 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: 96.0%

2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1→4)-2,3,6-tri-O-benzyl-β-D-glucopyranose (108811-27-4) → 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-glucono-1,5-lactone (88970-25-6)

Guidance literature:

In dichloromethane; acetic anhydride; dimethyl sulfoxide;

DOI:10.1071/C97015

Reference yield:

allyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1[*]4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside (84396-49-6) → 2,3,6-tri-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-glucono-1,5-lactone (88970-25-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 70 percent / camphor-10-sulfonic acid / Pd/C / methanol; CH₂Cl₂ / 1.) RT, overnight, 2.) reflux, 24 h

2: 96 percent / dimethylsulfoxide; acetic anhydride; CH₂Cl₂

With camphor-10-sulfonic acid; palladium on activated charcoal; In methanol; dichloromethane; acetic anhydride; dimethyl sulfoxide;

DOI:10.1071/C97015

Reference yield:

2,3,6-tri-O-benzyl-4-O-(2′,3′,4′,6′-tetra-O-benzyl-β-D-galactopyranosyl)-D-glucopyranose (108811-21-8,108811-27-4,115988-74-4,132683-15-9,148968-90-5) → 4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2,3,6-tri-O-benzyl-1,5-D-gluconolactone (88970-25-6)

Guidance literature:

With acetic anhydride; In dimethyl sulfoxide; at 10 ℃;

DOI:10.1002/chem.201300150

upstream raw materials:

benzyl bromide

LACTOSE

lactose octaacetate

2,3,6-tri-O-benzyl-4-O-(2′,3′,4′,6′-tetra-O-benzyl-β-D-galactopyranosyl)-D-glucopyranose

Downstream raw materials:

3-4)-tri-O-benzyl-β-D-glucopyranosyl>prop-1-ene

(1S)-(1(OH),2,4/1,3)-3,4-Di-O-benzyl-1-C-<(benzyloxy)methyl>-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-6,6-dichloro-5-oxo-1,2,3,4-cyclohexanetetrol

(1R)-2,3,6-Tri-O-benzyl-1-C-(dichloromethyl)-4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-D-glucitol

(1S)-(1(OH),2,4/1,3)-3,4-Di-O-benzyl-1-C-<(benzyloxy)methyl>-2-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-5-oxo-1,2,3,4-cyclohexanetetrol

Refernces

• 1、 Best, Wayne M.,Ferro, Vito,Harle, Julia,Stick, Robert V.,Tilbrook, D. Mathew G.. "The synthesis of some epoxyalkyl β-C-glycosides as potential inhibitors of β-glucan hydrolases". . p. 463 - 472. Retrieved 2007/10/03.