6-azido-3-O-benzyl-6-deoxy-1,2-O-(1-methylethylidene)-α-D-glucofuranose

Base Information

• Chemical Name: 6-azido-3-O-benzyl-6-deoxy-1,2-O-(1-methylethylidene)-α-D-glucofuranose
• CAS No.: 23313-05-5
• Molecular Formula: C₁₆H₂₁N₃O₅
• Molecular Weight: 335.36
• Mol file: 23313-05-5.mol

Synonyms:6-azido-3-O-benzyl-6-deoxy-1,2-O-(1-methylethylidene)-α-D-glucofuranose

Chemical Property of 6-azido-3-O-benzyl-6-deoxy-1,2-O-(1-methylethylidene)-α-D-glucofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-azido-3-O-benzyl-6-deoxy-1,2-O-(1-methylethylidene)-α-D-glucofuranose

There total 12 articles about 6-azido-3-O-benzyl-6-deoxy-1,2-O-(1-methylethylidene)-α-D-glucofuranose 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%

6-azido-3-O-benzyl-6-deoxy-1,2-O-(1-methylethylidene)-5-O-trimethylsilyl-α-D-glucofuranose → 6-azido-3-O-benzyl-6-deoxy-1,2-O-(1-methylethylidene)-α-D-glucofuranose (23313-05-5)

Guidance literature:

With potassium carbonate; In methanol;

DOI:10.1080/07328309908544029

Reference yield: 80.0%

(R)-2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl 4-methylbenzenesulfonate (23313-03-3) → 6-azido-3-O-benzyl-6-deoxy-1,2-O-(1-methylethylidene)-α-D-glucofuranose (23313-05-5)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 18h; Inert atmosphere;

DOI:10.1016/j.steroids.2013.11.022

Reference yield: 79.0%

3-O-benzyl 1,2-O-isopropylidene-5,6-O-sulfuryl-α-D-glucofuranose (158946-12-4) → 6-azido-3-O-benzyl-6-deoxy-1,2-O-(1-methylethylidene)-α-D-glucofuranose (23313-05-5)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 50 ℃; for 1h;

DOI:10.1016/S0008-6215(99)00124-X

upstream raw materials:

3-O-benzyl 1,2-O-isopropylidene-5,6-O-sulfuryl-α-D-glucofuranose

(R)-2-[(3aR,5R,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-hydroxyethyl 4-methylbenzenesulfonate

(1R)-1-((3aR,6S,6aR)-6-(benzyloxy)-2,2-dimethyltetrahydrofuro(2,3-d)(1,3)dioxol-5-yl)ethane-1,2-diol

benzyl bromide

Downstream raw materials:

6-azido-3-O-benzyl-6-deoxy-5-O-methyl-1,2-O-isopropylidene-α-D-glucofuranose

6-amino-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose

4-O-benzyl-N-benzyloxycarbonyl-1,5-dideoxy-1,5-imino-2-O-methyl-D-mannitol