(Z)-C-6-azido-2,3-O,O-dibenzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid

Base Information

• Chemical Name: (Z)-C-6-azido-2,3-O,O-dibenzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid
• CAS No.: 1617539-93-1
• Molecular Formula: C₂₀H₁₇N₃O₄
• Molecular Weight: 363.373
• Mol file: 1617539-93-1.mol

Synonyms:(Z)-C-6-azido-2,3-O,O-dibenzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid

Chemical Property of (Z)-C-6-azido-2,3-O,O-dibenzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (Z)-C-6-azido-2,3-O,O-dibenzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid

There total 5 articles about (Z)-C-6-azido-2,3-O,O-dibenzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid 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: 68.0%

Z-(2)-(3,4-bis(benzyloxy)-5-oxofuran-2(5H)-ylidine)ethyl 4-methylbenzenesulfonate (1617539-91-9) → (Z)-C-6-azido-2,3-O,O-dibenzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid (1617539-93-1)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 20 ℃;

DOI:10.1016/j.ejmech.2014.05.042

Reference yield:

(R)-3,4-bis(benzyloxy)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)furan-2(5H)-one (2871-84-3) → (Z)-C-6-azido-2,3-O,O-dibenzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid (1617539-93-1)

Guidance literature:

Multi-step reaction with 3 steps

1: acetic acid / methanol

2: pyridine / dichloromethane / 0 °C

3: sodium azide / acetonitrile / 20 - 80 °C

With pyridine; sodium azide; acetic acid; In methanol; dichloromethane; acetonitrile;

DOI:10.1039/c6ra25244c

Reference yield:

ascorbic acid (50-81-7,98966-42-8) → (Z)-C-6-azido-2,3-O,O-dibenzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid (1617539-93-1)

Guidance literature:

Multi-step reaction with 5 steps

1: acetyl chloride

2: potassium carbonate

3: acetic acid / methanol

4: pyridine / dichloromethane / 0 °C

5: sodium azide / acetonitrile / 20 - 80 °C

With pyridine; sodium azide; potassium carbonate; acetic acid; acetyl chloride; In methanol; dichloromethane; acetonitrile;

DOI:10.1039/c6ra25244c

upstream raw materials:

Z-⁽²⁾-(3,4-bis(benzyloxy)-5-oxofuran-2(5H)-ylidine)ethyl 4-methylbenzenesulfonate

ascorbic acid

5,6-O-isopropylidene-L-ascorbic acid

(R)-3,4-bis(benzyloxy)-5-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)furan-2(5H)-one

Downstream raw materials:

C₂₆H₂₇N₃O₅

5-(2-(4-benzyl-1H-1,2,3-triazol-1-yl)ethyl)-3,4-bis(benzyloxy)-5-hydroxy-1H-pyrrol-2(5H)-one

(Z)-5-(2-(4-benzyl-1H-1,2,3-triazol-1-yl)ethylidene)-3,4-bis(benzyloxy)furan-2(5H)-one

3,4-bis(benzyloxy)-5-hydroxy-5-(2-(4-phenyl-1H-1,2,3-triazol-1-yl)ethyl)-1H-pyrrol-2(5H)-one