2-azido-3-O-benzyl-4,6-O-benzylidene-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose

Base Information

• Chemical Name: 2-azido-3-O-benzyl-4,6-O-benzylidene-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose
• CAS No.: 138889-14-2
• Molecular Formula: C₂₆H₃₅N₃O₅Si
• Molecular Weight: 497.667
• Mol file: 138889-14-2.mol

Synonyms:2-azido-3-O-benzyl-4,6-O-benzylidene-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose

Chemical Property of 2-azido-3-O-benzyl-4,6-O-benzylidene-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-azido-3-O-benzyl-4,6-O-benzylidene-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose

There total 9 articles about 2-azido-3-O-benzyl-4,6-O-benzylidene-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-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: 95.0%

benzyl bromide (100-39-0) + 2-azido-4,6-O-benzylidene-2-deoxyl-1-O-tert-butyldimethylsilyl-β-D-glucopyranoside (138923-10-1) → 2-azido-3-O-benzyl-4,6-O-benzylidene-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose (138889-14-2)

Guidance literature:

With 4 A molecular sieve; silver(l) oxide; In dichloromethane; for 8h;

DOI:10.1002/chem.200390009

Reference yield: 65.0%

tert-butyldimethylsilyl-2-azido-2-deoxy-3,4,6-tri-O-trimethylsilyl-β-D-glucopyranoside + benzaldehyde (100-52-7) → 2-azido-3-O-benzyl-4,6-O-benzylidene-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose (138889-14-2)

Guidance literature:

tert-butyldimethylsilyl-2-azido-2-deoxy-3,4,6-tri-O-trimethylsilyl-β-D-glucopyranoside; benzaldehyde; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 2h; Inert atmosphere; Molecular sieve;

With triethylsilane; In dichloromethane; at 0 ℃; for 6h; Temperature; Inert atmosphere; Molecular sieve;

DOI:10.1002/ejoc.202000923

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → 2-azido-3-O-benzyl-4,6-O-benzylidene-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose (138889-14-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 29.0 g / p-TsOH*H₂O / acetonitrile / 20 °C

2: 95 percent / molecular sieves 4 Angstroem; Ag₂O / CH₂Cl₂ / 8 h

With 4 A molecular sieve; toluene-4-sulfonic acid; silver(l) oxide; In dichloromethane; acetonitrile;

DOI:10.1002/chem.200390009

upstream raw materials:

benzyl bromide

2-azido-4,6-O-benzylidene-2-deoxyl-1-O-tert-butyldimethylsilyl-β-D-glucopyranoside

(+)-D-glucosamine hydrochloride

benzaldehyde dimethyl acetal

Downstream raw materials:

2-azido-2-deoxy-3,4-O-dibenzyl-1-O-tert-butyldimethylsilyl-β-D-glucopyranoside

2-azido-6-O-benzoyl-3-O-benzyl-2-deoxy-4-O-levulinoyl-α-D-glucopyranosyl trichloroacetimidate

2-azido-6-O-benzoyl-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-4-O-levulinoyl-β-D-glucopyranose

2-azido-6-O-benzoyl-3-O-benzyl-1-O-(tert-butyldimethylsilyl)-2-deoxy-β-D-glucopyranose