Nitro(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)methane

Base Information

• Chemical Name: Nitro(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)methane
• CAS No.: 136738-61-9
• Molecular Formula: C₁₈H₂₁NO₉
• Molecular Weight: 395.366
• Mol file: 136738-61-9.mol

Synonyms:Nitro(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)methane

Chemical Property of Nitro(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)methane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Nitro(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)methane

There total 6 articles about Nitro(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)methane 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: 90.0%

acetic anhydride (108-24-7) + 2,6-anhydro-5,7-O-benzylidene-1-deoxy-1-nitro-D-glycero-D-gulo-heptitol (136738-59-5) → Nitro(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)methane (136738-61-9)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; 1.) 0 deg C, 6 h, 2.) r.t., 2 h;

DOI:10.1021/jo00110a024

Reference yield: 61.0%

acetic anhydride (108-24-7) + 2,6-anhydro-5,7-O-benzylidene-1-deoxy-1-nitro-D-glycero-D-guloheptitol (136738-59-5) → 3,4-di-O-acetyl-2,6-anhydro-5,7-O-benzylidene-1-deoxy-1-nitro-D-glycero-D-guloheptitol (136738-61-9)

Guidance literature:

With dmap; triethylamine; In tetrahydrofuran; 1) 0 deg C, 1 h, 2) RT, 15 h;

DOI:10.1016/S0040-4020(01)86545-5

Reference yield:

(2R,3R)-2,3-Dihydroxy-3-((2R,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)-propionaldehyde (83212-64-0) → Nitro(2,3-di-O-acetyl-4,6-O-benzylidene-β-D-glucopyranosyl)methane (136738-61-9)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium methylate; methanol

2: sodium acetate

With methanol; sodium methylate; sodium acetate;

DOI:10.1021/ja01212a037

upstream raw materials:

acetic anhydride

2,6-anhydro-5,7-O-benzylidene-1-deoxy-1-nitro-D-glycero-D-gulo-heptitol

(2R,3R)-2,3-Dihydroxy-3-((2R,4R,5R)-5-hydroxy-2-phenyl-[1,3]dioxan-4-yl)-propionaldehyde

2,6-anhydro-5,7-O-benzylidene-1-deoxy-1-nitro-D-glycero-D-guloheptitol