BETA-D-GLUCOPYRANOSYL NITROMETHANE

Base Information

• Chemical Name: BETA-D-GLUCOPYRANOSYL NITROMETHANE
• CAS No.: 81846-60-8
• Molecular Formula: C7H13NO7
• Molecular Weight: 223.18062
• Mol file: 81846-60-8.mol

Synonyms:BETA-D-GLUCOPYRANOSYL NITROMETHANE;b-D-Glucopyranosylnitromethane;SS-D-GLUCOPYRANOSYL NITROMETHANE;nitroMethyl β-D-glucopyranoside

Chemical Property of BETA-D-GLUCOPYRANOSYL NITROMETHANE

Chemical Property:

• Melting Point: 174-175 °C
• Boiling Point: 497.2±45.0 °C(Predicted)
• PKA: 7.18±0.70(Predicted)
• PSA: 135.97000
• Density: 1.584±0.06 g/cm3(Predicted)
• LogP: -2.37130

Purity/Quality:

98%Min ^*data from raw suppliers

b-D-Glucopyranosyl nitromethane ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of BETA-D-GLUCOPYRANOSYL NITROMETHANE

There total 12 articles about BETA-D-GLUCOPYRANOSYL NITROMETHANE 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: 57.0%

β-D-glucose (492-61-5) + nitromethane (75-52-5) → nitromethyl β-D-glucopyranoside (81846-60-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In pyridine; at 50 ℃; for 24h;

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

Reference yield: 40.0%

1,2?dideoxy?1?nitro?D?manno?hept?1?enitol peracetate (16749-54-5) → 2,6?anhydro?1?deoxy?1?nitro?D?glycero?D?galacto?heptitol (93302-92-2) + 2,6-anhydro-7-deoxy-7-nitro-D-glycero-D-manno-heptitol (81812-47-7,81846-60-8,81846-61-9,81846-64-2,92283-28-8,92283-29-9,93302-92-2)

Guidance literature:

With methanol; sodium methylate; at 30 ℃; for 16h;

DOI:10.1007/s00706-020-02614-5

Reference yield: 36.0%

1,2?dideoxy?1?nitro?D?manno?hept?1?enitol peracetate (16749-54-5) → 3,6?anhydro?7?deoxy?7?nitro?D?glycero?D?manno?heptitol + 2,5?anhydro?1?deoxy?1?nitro?D?glycero?D?galacto?heptitol + C8H17NO8 + C8H17NO8 + 2,6-anhydro-7-deoxy-7-nitro-D-glycero-D-manno-heptitol (81812-47-7,81846-60-8,81846-61-9,81846-64-2,92283-28-8,92283-29-9,93302-92-2)

Guidance literature:

With methanol; sodium methylate; at 30 ℃; for 0.08h;

DOI:10.1007/s00706-020-02614-5

upstream raw materials:

1-Desoxy-1-nitro-D-glycero-D-gulo-heptitol

D-Glucose

nitromethane

D-glucose

Downstream raw materials:

2,6-anhydro-1-benzyloxycarboxamido-1-deoxy-D-glycero-D-guloheptitol

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

(2S,3S,4R,5R,6S)-6-(Benzyloxycarbonylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid methyl ester

(2S,3S,4R,5R,6S)-6-(Benzyloxycarbonylamino-methyl)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid

Refernces

• 1、 Phiasivongsa, Pasit,Samoshin, Vyacheslav V.,Gross, Paul H.. "Henry condensations with 4,6-O-benzylidenylated and non-protected D-glucose and L-fucose via DBU-catalysis". . p. 5495 - 5498. Retrieved 2007/10/03.
• 2、 -. "Use of D-glucopyranuronic acids and their derivatives for incorporation in pharmacologically active peptides and their salts". . . Retrieved 2008/06/13.