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

Base Information

• Chemical Name: 2,6-anhydro-5,7-O-benzylidene-1-deoxy-1-nitro-D-glycero-D-gulo-heptitol
• CAS No.: 136738-59-5
• Molecular Formula: C₁₄H₁₇NO₇
• Molecular Weight: 311.291
• Mol file: 136738-59-5.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about 2,6-anhydro-5,7-O-benzylidene-1-deoxy-1-nitro-D-glycero-D-gulo-heptitol 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: 96.0%

nitromethyl β-D-glucopyranoside (81846-60-8) + benzaldehyde dimethyl acetal (1125-88-8) → 2,6-anhydro-5,7-O-benzylidene-1-deoxy-1-nitro-D-glycero-D-gulo-heptitol (136738-59-5)

Guidance literature:

With toluene-4-sulfonic acid; In 1,2-dimethoxyethane; for 20h;

DOI:10.1016/S0008-6215(97)00203-6

Reference yield: 83.3%

nitromethane (75-52-5) + 4,6-O-benzylidene-D-glucose (3006-41-5,20771-09-9,25152-90-3,97232-16-1,104022-77-7,113566-67-9,113566-68-0) → 2,6-anhydro-5,7-O-benzylidene-1-deoxy-1-nitro-D-glycero-D-gulo-heptitol (136738-59-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 48h; Inert atmosphere;

DOI:10.1016/j.bmc.2013.06.002

Reference yield: 69.0%

(4aR,6S,7R,8R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-6,7,8-triol (25152-90-3) + nitromethane (75-52-5) → 2,6-anhydro-5,7-O-benzylidene-1-deoxy-1-nitro-D-glycero-D-guloheptitol (136738-59-5)

Guidance literature:

With 2-hydroxypyridin; 3 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; for 72h; Ambient temperature;

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

upstream raw materials:

methanol

nitromethane

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

sodium methylate

Downstream raw materials:

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

3,4-di-O-acetyl-2,6-anhydro-5,7-O-benzylidene-1-deoxy-1-nitro-D-glycero-D-guloheptitol

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

C-(4,6-O-benzylidene-β-D-glucopyranosyl) methylamine