1,2-isopropyridene-3-(O-2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)glycerol

Base Information

• Chemical Name: 1,2-isopropyridene-3-(O-2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)glycerol
• CAS No.: 123806-53-1
• Molecular Formula: C₄₀H₄₆O₈
• Molecular Weight: 654.8
• Mol file: 123806-53-1.mol

Synonyms:1,2-isopropyridene-3-(O-2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)glycerol

Chemical Property of 1,2-isopropyridene-3-(O-2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)glycerol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,2-isopropyridene-3-(O-2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)glycerol

There total 2 articles about 1,2-isopropyridene-3-(O-2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)glycerol 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:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) + [(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl trifluoromethanesulfonate (76679-39-5) → 1,2-isopropyridene-3-(O-2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)glycerol (123806-53-1)

Guidance literature:

In tetrahydrofuran; methanol; chloroform;

Reference yield:

phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside (38184-10-0) + (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol (100-79-8,36543-79-0) → 1,2-isopropyridene-3-(O-2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)glycerol (123806-53-1) + 1,2-isopropyridene-3-(O-2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)glycerol

Guidance literature:

phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside; (R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol; In dichloromethane; at 20 ℃; for 0.25h; Molecular sieve; Inert atmosphere;

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -80 ℃; for 3.5h; Overall yield = 67 %; Overall yield = 35.4 mg; diastereoselective reaction; Molecular sieve; Inert atmosphere;

DOI:10.1002/ejoc.201700671

Reference yield:

1,2-isopropyridene-3-(O-2,3,4,6-tetra-O-benzyl-D-glucopyranosyl)glycerol (123806-53-1) → (2R) 1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-glycerol (182212-00-6)

Guidance literature:

In water; acetic acid;

upstream raw materials:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]methyl trifluoromethanesulfonate

phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside

(R,S)-2,2-dimethyl-1,3-dioxolane-4-methanol

Downstream raw materials:

(2R) 1-O-(2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)-glycerol