methyl 6,7-dideoxy-6-(2,4-dinitrophenyl)amino-L-glycero-D-gluco-heptopyranoside

Base Information

• Chemical Name: methyl 6,7-dideoxy-6-(2,4-dinitrophenyl)amino-L-glycero-D-gluco-heptopyranoside
• CAS No.: 83093-94-1
• Molecular Formula: C₁₄H₁₉N₃O₉
• Molecular Weight: 373.32

Synonyms:methyl 6,7-dideoxy-6-(2,4-dinitrophenyl)amino-L-glycero-D-gluco-heptopyranoside

Chemical Property of methyl 6,7-dideoxy-6-(2,4-dinitrophenyl)amino-L-glycero-D-gluco-heptopyranoside

Chemical Property:

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Technology Process of methyl 6,7-dideoxy-6-(2,4-dinitrophenyl)amino-L-glycero-D-gluco-heptopyranoside

There total 8 articles about methyl 6,7-dideoxy-6-(2,4-dinitrophenyl)amino-L-glycero-D-gluco-heptopyranoside 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: 18.0%

2,4-Dinitrofluorobenzene (70-34-8,65727-75-5) + methyl 6-amino-6,7-dideoxy-β-L-glycero-D-gluco-heptopyranoside (83093-93-0) → methyl 6,7-dideoxy-6-(2,4-dinitrophenyl)amino-L-glycero-D-gluco-heptopyranoside (83093-94-1)

Guidance literature:

With sodium hydrogencarbonate; In ethanol; for 2h; Ambient temperature;

DOI:10.1016/S0008-6215(00)82223-5

Reference yield:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) → methyl 6,7-dideoxy-6-(2,4-dinitrophenyl)amino-L-glycero-D-gluco-heptopyranoside (83093-94-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 92 percent / dimethyl sulfoxide, phosphoric acid, dicyclohexylcarbodiimide / benzene; pyridine / 7 h / Ambient temperature

2: 63 percent / pyridine / 3 h / Ambient temperature

3: lithium aluminium hydride / diethyl ether / 1 h / Ambient temperature

4: triethylamine / benzene / 2 h / 0 °C

5: hydrogen / Raney nickel / methanol; H₂O / 96 h / 66195.7 Torr

6: hydrogen / 10percent palladium-charcoal / methanol; H₂O; acetic acid

7: 18 percent / sodium hydrogencarbonate / ethanol / 2 h / Ambient temperature

With lithium aluminium tetrahydride; phosphoric acid; hydrogen; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; nickel; In pyridine; methanol; diethyl ether; ethanol; water; acetic acid; benzene;

DOI:10.1016/S0008-6215(00)82223-5

Reference yield:

methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (7177-79-9,13035-24-0,29600-81-5,33164-02-2,51842-18-3,52526-59-7,78738-75-7,99212-27-8,101312-02-1,107795-23-3,108739-87-3,129170-92-9,13225-19-9) → methyl 6,7-dideoxy-6-(2,4-dinitrophenyl)amino-L-glycero-D-gluco-heptopyranoside (83093-94-1)

Guidance literature:

Multi-step reaction with 8 steps

1: lithium aluminium hydride-aluminium chloride

2: 92 percent / dimethyl sulfoxide, phosphoric acid, dicyclohexylcarbodiimide / benzene; pyridine / 7 h / Ambient temperature

3: 63 percent / pyridine / 3 h / Ambient temperature

4: lithium aluminium hydride / diethyl ether / 1 h / Ambient temperature

5: triethylamine / benzene / 2 h / 0 °C

6: hydrogen / Raney nickel / methanol; H₂O / 96 h / 66195.7 Torr

7: hydrogen / 10percent palladium-charcoal / methanol; H₂O; acetic acid

8: 18 percent / sodium hydrogencarbonate / ethanol / 2 h / Ambient temperature

With lithium aluminium tetrahydride; aluminium trichloride; phosphoric acid; hydrogen; sodium hydrogencarbonate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; nickel; In pyridine; methanol; diethyl ether; ethanol; water; acetic acid; benzene;

DOI:10.1016/S0008-6215(00)82223-5

upstream raw materials:

2,4-Dinitrofluorobenzene

methyl 6-amino-6,7-dideoxy-β-L-glycero-D-gluco-heptopyranoside

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

methyl 2,3-di-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

Downstream raw materials:

N-(2,4-dinitro-phenyl)-L-alanine

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