5,7-O-benzylidene-1,2-dideoxy-1-nitro-2-nitromethyl-D-glucoheptitol

Base Information

• Chemical Name: 5,7-O-benzylidene-1,2-dideoxy-1-nitro-2-nitromethyl-D-glucoheptitol
• CAS No.: 136738-60-8
• Molecular Formula: C₁₅H₂₀N₂O₉
• Molecular Weight: 372.332
• Mol file: 136738-60-8.mol

Synonyms:5,7-O-benzylidene-1,2-dideoxy-1-nitro-2-nitromethyl-D-glucoheptitol

Chemical Property of 5,7-O-benzylidene-1,2-dideoxy-1-nitro-2-nitromethyl-D-glucoheptitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5,7-O-benzylidene-1,2-dideoxy-1-nitro-2-nitromethyl-D-glucoheptitol

There total 4 articles about 5,7-O-benzylidene-1,2-dideoxy-1-nitro-2-nitromethyl-D-glucoheptitol 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: 61.0%

4,6-O-benzylidene-β-D-glucopyranosyl (104022-77-7) + nitromethane (75-52-5) → 2,6-anhydro-5,7-O-benzylidene-1-deoxy-1-nitro-D-glycero-D-guloheptitol (136738-59-5) + 5,7-O-benzylidene-1-deoxy-1-nitro-D-glycero-D-gulo-heptitol (95239-58-0) + 5,7-O-benzylidene-1,2-dideoxy-1-nitro-2-nitromethyl-D-glucoheptitol (136738-60-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at 20 ℃; for 50h;

DOI:10.1016/S0040-4039(03)01328-5

Reference yield: 39.0%

(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) + 5,7-O-benzylidene-1-deoxy-1-nitro-D-glycero-D-gulo-heptitol (95239-58-0) + 5,7-O-benzylidene-1,2-dideoxy-1-nitro-2-nitromethyl-D-glucoheptitol (136738-60-8)

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

Reference yield:

β-D-glucose (492-61-5) → 5,7-O-benzylidene-1,2-dideoxy-1-nitro-2-nitromethyl-D-glucoheptitol (136738-60-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 42 percent / p-toluenesulfonic acid monohydrate / dimethylformamide / 8 h / 40 °C / 2 Torr

2: 6.3 percent / DBU, 2-hydroxypyridine, molecular sieves (3 Angstroem) / tetrahydrofuran / 72 h / Ambient temperature

With 2-hydroxypyridin; 3 A molecular sieve; toluene-4-sulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; N,N-dimethyl-formamide;

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

upstream raw materials:

(4aR,6S,7R,8R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-6,7,8-triol

nitromethane

4,6-O-benzylidene-β-D-glucopyranosyl

β-D-glucose