methyl (methyl 4-azido-3,4-dideoxy-D-arabino-heptulopyranosid)onate 7-(diphenylphosphate)

Base Information

• Chemical Name: methyl (methyl 4-azido-3,4-dideoxy-D-arabino-heptulopyranosid)onate 7-(diphenylphosphate)
• CAS No.: 156726-67-9
• Molecular Formula: C₂₁H₂₄N₃O₉P
• Molecular Weight: 493.41
• Mol file: 156726-67-9.mol

Synonyms:methyl (methyl 4-azido-3,4-dideoxy-D-arabino-heptulopyranosid)onate 7-(diphenylphosphate)

Chemical Property of methyl (methyl 4-azido-3,4-dideoxy-D-arabino-heptulopyranosid)onate 7-(diphenylphosphate)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (methyl 4-azido-3,4-dideoxy-D-arabino-heptulopyranosid)onate 7-(diphenylphosphate)

There total 7 articles about methyl (methyl 4-azido-3,4-dideoxy-D-arabino-heptulopyranosid)onate 7-(diphenylphosphate) 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: 100.0%

methyl (methyl 4-azido-3,4-dideoxy-D-arabino-heptulopyranosid)onate (156726-66-8) + chlorophosphoric acid diphenyl ester (2524-64-3) → methyl (methyl 4-azido-3,4-dideoxy-D-arabino-heptulopyranosid)onate 7-(diphenylphosphate) (156726-67-9)

Guidance literature:

With pyridine;

DOI:10.1021/ja00038a090

Reference yield:

methyl (methyl 3-deoxy-α-D-arabino-2-heptulopyranosid)onate (2880-95-7,85549-51-5) → methyl (methyl 4-azido-3,4-dideoxy-D-arabino-heptulopyranosid)onate 7-(diphenylphosphate) (156726-67-9)

Guidance literature:

Multi-step reaction with 5 steps

1: p-toluenesulfonic acid / dimethylformamide / 4 h / 72 °C / 35 Torr

2: 1.) (COCl)2, DMSO, Et₃N / 1.) CH₂Cl₂, -70 deg C, 45 min, 2.) CH₂Cl₂, from -70 to RT

3: 1.) NaBH₄, 2.) pyridine, 3.) NaN₃

4: 81 percent / 70percent aq. AcOH / 24 h / 39 °C

5: 100 percent / pyridine / 45 h / Ambient temperature

With pyridine; sodium tetrahydroborate; sodium azide; oxalyl dichloride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; In N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(94)84211-6

Reference yield:

methyl (methyl 5,7-O-benzylidene-3-deoxy-D-arabino-heptulopyranosid)onate (156726-61-3) → methyl (methyl 4-azido-3,4-dideoxy-D-arabino-heptulopyranosid)onate 7-(diphenylphosphate) (156726-67-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) (COCl)2, DMSO, Et₃N / 1.) CH₂Cl₂, -70 deg C, 45 min, 2.) CH₂Cl₂, from -70 to RT

2: 1.) NaBH₄, 2.) pyridine, 3.) NaN₃

3: 81 percent / 70percent aq. AcOH / 24 h / 39 °C

4: 100 percent / pyridine / 45 h / Ambient temperature

With pyridine; sodium tetrahydroborate; sodium azide; oxalyl dichloride; acetic acid; dimethyl sulfoxide; triethylamine;

DOI:10.1016/0008-6215(94)84211-6

upstream raw materials:

methyl (methyl 4-azido-3,4-dideoxy-D-arabino-heptulopyranosid)onate

chlorophosphoric acid diphenyl ester

methyl (methyl 3-deoxy-α-D-arabino-2-heptulopyranosid)onate

methyl (methyl 5,7-O-benzylidene-3-deoxy-4-oxo-D-arabino-heptulopyranosid)onate