3-O-acetyl-1,2-O-isopropylidene-6-O-(p-nitrobenzoyl)-D-glucofuranose

Base Information

• Chemical Name: 3-O-acetyl-1,2-O-isopropylidene-6-O-(p-nitrobenzoyl)-D-glucofuranose
• CAS No.: 104652-55-3
• Molecular Formula: C₁₈H₂₁NO₁₀
• Molecular Weight: 411.365
• Mol file: 104652-55-3.mol

Synonyms:3-O-acetyl-1,2-O-isopropylidene-6-O-(p-nitrobenzoyl)-D-glucofuranose

Chemical Property of 3-O-acetyl-1,2-O-isopropylidene-6-O-(p-nitrobenzoyl)-D-glucofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-O-acetyl-1,2-O-isopropylidene-6-O-(p-nitrobenzoyl)-D-glucofuranose

There total 1 articles about 3-O-acetyl-1,2-O-isopropylidene-6-O-(p-nitrobenzoyl)-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: 93.0%

3-O-acetyl-1,2-O-isopropylidene-α-D-glucofuranose (24807-96-3) + 4-nitro-benzoyl chloride (122-04-3) → 3-O-acetyl-1,2-O-isopropylidene-6-O-(p-nitrobenzoyl)-D-glucofuranose (104652-55-3)

Guidance literature:

In pyridine; at -40 ℃;

DOI:10.1246/bcsj.59.1397

Reference yield: 94.0%

methanesulfonyl chloride (124-63-0) + 3-O-acetyl-1,2-O-isopropylidene-6-O-(p-nitrobenzoyl)-D-glucofuranose (104652-55-3) → 3-O-acetyl-1,2-O-isopropylidene-5-O-methylsulfonyl-6-O-(p-nitrobenzoyl)-D-glucofuranose (104652-56-4)

Guidance literature:

In pyridine; for 3h; Ambient temperature;

DOI:10.1246/bcsj.59.1397

Reference yield:

3-O-acetyl-1,2-O-isopropylidene-6-O-(p-nitrobenzoyl)-D-glucofuranose (104652-55-3) → methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-L-idopyranoside (21893-05-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / pyridine / 3 h / Ambient temperature

2: 2.2 g / 1M methanolic ammonia / 6 h / Ambient temperature

3: 68 percent / sodium azide, ammonium chloride / dimethylformamide / 1.2 h / Heating

4: 1.) 1.4 M methanolic hydrochloric acid / 1.) reflux, 1.5 h; 2.) pyridine, roomtemp., overnight

With hydrogenchloride; sodium azide; ammonium chloride; ammonia; In pyridine; N,N-dimethyl-formamide;

DOI:10.1246/bcsj.59.1397

upstream raw materials:

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

4-nitro-benzoyl chloride

Downstream raw materials:

3-O-acetyl-1,2-O-isopropylidene-5-O-methylsulfonyl-6-O-(p-nitrobenzoyl)-D-glucofuranose

methyl 6-azido-6-deoxy-α-D-glucopyranoside

methyl 6-amino-6-deoxy-α-D-glucopyranoside

methyl 2,3,4-tri-O-acetyl-6-azido-6-deoxy-β-L-idopyranoside