methyl 2,4-anhydro-5-azido-5-deoxy-3-O-benzyl-D-ribonate

Base Information

• Chemical Name: methyl 2,4-anhydro-5-azido-5-deoxy-3-O-benzyl-D-ribonate
• CAS No.: 1294500-47-2
• Molecular Formula: C₁₃H₁₅N₃O₄
• Molecular Weight: 277.28
• Mol file: 1294500-47-2.mol

Synonyms:

Chemical Property of methyl 2,4-anhydro-5-azido-5-deoxy-3-O-benzyl-D-ribonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 2,4-anhydro-5-azido-5-deoxy-3-O-benzyl-D-ribonate

There total 3 articles about methyl 2,4-anhydro-5-azido-5-deoxy-3-O-benzyl-D-ribonate 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:

methanol (67-56-1) + 5-azido-3-O-benzyl-5-deoxy-D-arabinono-1,4-lactone (1294500-46-1) → methyl 2,4-anhydro-5-azido-5-deoxy-3-O-benzyl-D-ribonate (1294500-47-2) + methyl 2,4-anhydro-5-azido-5-deoxy-3-O-benzyl-D-ribonate

Guidance literature:

5-azido-3-O-benzyl-5-deoxy-D-arabinono-1,4-lactone; With pyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -40 ℃; Molecular sieve;

methanol; With potassium carbonate; at -25 ℃; for 2h; optical yield given as %de;

DOI:10.1002/chem.201002895

Reference yield:

(3S,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2,3,4-triol (168608-39-7) → methyl 2,4-anhydro-5-azido-5-deoxy-3-O-benzyl-D-ribonate (1294500-47-2) + methyl 2,4-anhydro-5-azido-5-deoxy-3-O-benzyl-D-ribonate

Guidance literature:

Multi-step reaction with 8 steps

1.1: camphor-10-sulfonic acid; copper(II) sulfate / pH 2

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 °C

3.1: tetrabutyl ammonium fluoride / tetrahydrofuran

4.1: pyridine / 60 °C

5.1: sodium azide / N,N-dimethyl-formamide / 7 h / 95 °C

6.1: acetic acid / water / 110 °C / Reflux

7.1: bromine; barium carbonate / 1,4-dioxane; water / 6 h / Inert atmosphere

8.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / -40 °C / Molecular sieve

8.2: 2 h / -25 °C

With pyridine; sodium azide; trifluoromethylsulfonic anhydride; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; bromine; sodium hydride; copper(II) sulfate; acetic acid; barium carbonate; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1002/chem.201002895

Reference yield:

C12H15N3O4 → methyl 2,4-anhydro-5-azido-5-deoxy-3-O-benzyl-D-ribonate (1294500-47-2) + methyl 2,4-anhydro-5-azido-5-deoxy-3-O-benzyl-D-ribonate

Guidance literature:

Multi-step reaction with 2 steps

1.1: bromine; barium carbonate / 1,4-dioxane; water / 6 h / Inert atmosphere

2.1: pyridine; trifluoromethylsulfonic anhydride / dichloromethane / -40 °C / Molecular sieve

2.2: 2 h / -25 °C

With pyridine; trifluoromethylsulfonic anhydride; bromine; barium carbonate; In 1,4-dioxane; dichloromethane; water;

DOI:10.1002/chem.201002895

upstream raw materials:

methanol

5-azido-3-O-benzyl-5-deoxy-D-arabinono-1,4-lactone

(3S,4S,5R)-5-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-2,3,4-triol