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

Base Information

• Chemical Name: 6-azido-3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose
• CAS No.: 121195-24-2
• Molecular Formula: C₂₃H₂₇N₃O₅
• Molecular Weight: 425.484
• Mol file: 121195-24-2.mol

Synonyms:6-azido-3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose

Chemical Property of 6-azido-3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-azido-3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose

There total 5 articles about 6-azido-3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-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: 89.0%

6-azido-3-O-benzyl-6-deoxy-1,2-O-(1-methylethylidene)-α-D-glucofuranose (23313-05-5) + benzyl bromide (100-39-0) → 6-azido-3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose (121195-24-2)

Guidance literature:

With sodium hydride; In tetrahydrofuran; for 3h;

DOI:10.1039/c7ra10899k

Reference yield: 68.0%

3,5-di-O-acetyl-6-deoxy-1,2-O-isopropylidene-6-azido-α-D-glucofuranose (65371-16-6) + benzyl bromide (100-39-0) → 6-azido-3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose (121195-24-2)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; at 35 ℃; for 18h;

DOI:10.1016/0040-4020(89)80060-2

Reference yield:

1,2-O-isopropylidene-α-D-glucofuranose (18549-40-1) → 6-azido-3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose (121195-24-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / pyridine / 12 h / -14 °C

2: 92 percent / NaN₃ / dimethylformamide / 15 h / 40 °C

3: 68 percent / NaH, tetrabutylammonium iodide / tetrahydrofuran / 18 h / 35 °C

With sodium azide; tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; pyridine; N,N-dimethyl-formamide;

DOI:10.1016/0040-4020(89)80060-2

upstream raw materials:

3,5-di-O-acetyl-6-deoxy-1,2-O-isopropylidene-6-azido-α-D-glucofuranose

benzyl bromide

1,2-O-isopropylidene-α-D-glucofuranose

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose

Downstream raw materials:

6-nitro-3,5-di-O-benzyl-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose

(1S,4S,5S,6R,7R)-6,7-bis(benzyloxy)-5-nitro-2-oxabicyclo[2.2.1]heptan-3-one

3,5-di-O-benzyl-6-deoxy-6-nitro-D-glucono-1,4-lactone

methyl 3,5-di-O-benzyl-6-deoxy-6-nitro-α-D-glucofuranoside