6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl chloride

Base Information

• Chemical Name: 6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl chloride
• CAS No.: 42869-68-1
• Molecular Formula: C₂₇H₂₈ClN₃O₄
• Molecular Weight: 493.99
• Mol file: 42869-68-1.mol

Synonyms:6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl chloride

Chemical Property of 6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl chloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl chloride

There total 1 articles about 6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl chloride 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:

→ 6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl chloride (42869-68-1)

Guidance literature:

1-Methyl-2,3,4-tri-O-acetyl-6-azido-6-desoxy-α-D-glucopyranose, Azidierung;

DOI:10.1246/bcsj.49.1975

Reference yield: 52.0%

6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl chloride (42869-68-1) + 1-[(2-benzyloxy-3-N-benzyloxycarbonyl)-L-isoserinyl]-3,3-di-N-benzyloxycarbonylgaramine (845258-90-4) → [2-(6-azidomethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-5-(2-benzyloxy-3-benzyloxycarbonylamino-propionylamino)-4-(3,5-dihydroxy-5-methyl-4-methylamino-tetrahydro-pyran-2-yloxy)-3-hydroxy-cyclohexyl]-carbamic acid benzyl ester

Guidance literature:

6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl chloride; 1-[(2-benzyloxy-3-N-benzyloxycarbonyl)-L-isoserinyl]-3,3"-di-N-benzyloxycarbonylgaramine; With 4 A molecular sieve; silver trifluoromethanesulfonate; In 1,4-dioxane; benzene; at 20 ℃; for 12h;

With silver trifluoromethanesulfonate; In 1,4-dioxane; benzene; at 0 ℃; for 5h;

DOI:10.1016/j.tetlet.2004.11.130

Reference yield:

6-azido-2,3,4-tri-O-benzyl-6-deoxy-α-D-glucopyranosyl chloride (42869-68-1) → isepamicin (58152-03-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: silver triflate; 4 Angstroem molecular sieves / benzene; dioxane / 12 h / 20 °C

1.2: 52 percent / silver triflate / benzene; dioxane / 5 h / 0 °C

2.1: 57 percent / hydrogen / Pd/C / methanol; tetrahydrofuran

With 4 A molecular sieve; hydrogen; silver trifluoromethanesulfonate; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; benzene;

DOI:10.1016/j.tetlet.2004.11.130

Downstream raw materials:

isepamicin