benzyl 4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Base Information

• Chemical Name: benzyl 4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside
• CAS No.: 207917-28-0
• Molecular Formula: C₅₅H₅₄N₄O₁₁
• Molecular Weight: 947.054
• Mol file: 207917-28-0.mol

Synonyms:benzyl 4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property of benzyl 4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

There total 3 articles about benzyl 4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside 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-[(2R,3R,4R,5S,6R)-5-((2S,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-2,4-bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-3-yl]-isoindole-1,3-dione → benzyl 4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (207917-28-0)

Guidance literature:

With toluene-4-sulfonic acid; In acetonitrile; at 50 ℃; for 1h; Yield given;

DOI:10.1007/bf02495661

Reference yield:

benzyl 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (80035-35-4) → benzyl 4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (207917-28-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / Et₃N, DMAP / dimethylformamide / 0.5 h / 20 °C

2: 4 Angstroem MS, BF₃*Et₂O / acetonitrile; CH₂Cl₂ / 1 h / -40 °C

3: TsOH*H₂O / acetonitrile / 1 h / 50 °C

With dmap; 4 Angstroem MS; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; triethylamine; In dichloromethane; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1007/bf02495661

Reference yield:

2-[(2R,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-tetrahydro-pyran-3-yl]-isoindole-1,3-dione (207917-19-9) → benzyl 4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside (207917-28-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 4 Angstroem MS, BF₃*Et₂O / acetonitrile; CH₂Cl₂ / 1 h / -40 °C

2: TsOH*H₂O / acetonitrile / 1 h / 50 °C

With 4 Angstroem MS; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; In dichloromethane; acetonitrile;

DOI:10.1007/bf02495661

upstream raw materials:

benzyl 3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

2-[(2R,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-5-hydroxy-tetrahydro-pyran-3-yl]-isoindole-1,3-dione

Downstream raw materials:

C₆₆H₇₆N₄O₁₆

benzyl 6-O-[4-O-acetyl-3-O-(4-methoxybenzyl)-2-O-methyl-α-L-fucopyranosyl]-4-O-(2-azido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside