2,3,5-tri-O-benzyl-4-deoxy-4-azido-D-ribitol

Base Information

• Chemical Name: 2,3,5-tri-O-benzyl-4-deoxy-4-azido-D-ribitol
• CAS No.: 1437658-02-0
• Molecular Formula: C₂₆H₂₉N₃O₄
• Molecular Weight: 447.534
• Mol file: 1437658-02-0.mol

Synonyms:2,3,5-tri-O-benzyl-4-deoxy-4-azido-D-ribitol

Chemical Property of 2,3,5-tri-O-benzyl-4-deoxy-4-azido-D-ribitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,5-tri-O-benzyl-4-deoxy-4-azido-D-ribitol

There total 8 articles about 2,3,5-tri-O-benzyl-4-deoxy-4-azido-D-ribitol 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: 84.0%

2,3,5-tri-O-benzyl-4-deoxy-4-azido-1-O-trityl-D-ribitol (1437657-99-2) → 2,3,5-tri-O-benzyl-4-deoxy-4-azido-D-ribitol (1437658-02-0)

Guidance literature:

With toluene-4-sulfonic acid; In methanol; chloroform; for 6h;

DOI:10.1021/ol4012053

Reference yield:

benzyl bromide (100-39-0) → 2,3,5-tri-O-benzyl-4-deoxy-4-azido-D-ribitol (1437658-02-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: acetyl chloride

1.2: 2 h / 20 °C

2.1: sulfuric acid / acetic acid / 1 h / 100 °C

3.1: sodium tetrahydroborate / ethanol / 5 h / 0 - 20 °C

4.1: triethylamine; dmap / dichloromethane / 144 h

5.1: pyridine / 0 - 4 °C

6.1: sodium azide; 15-crown-5; tetra(n-butyl)ammonium hydrogensulfate / N,N-dimethyl-formamide / 48 h / 100 °C

7.1: toluene-4-sulfonic acid / methanol; chloroform / 6 h

With pyridine; dmap; sodium tetrahydroborate; sodium azide; 15-crown-5; sulfuric acid; tetra(n-butyl)ammonium hydrogensulfate; toluene-4-sulfonic acid; triethylamine; acetyl chloride; In methanol; ethanol; dichloromethane; chloroform; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/ol4012053

Reference yield:

L-arabinofuranose (87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2,36562-42-2) → 2,3,5-tri-O-benzyl-4-deoxy-4-azido-D-ribitol (1437658-02-0)

Guidance literature:

Multi-step reaction with 7 steps

1.1: acetyl chloride

1.2: 2 h / 20 °C

2.1: sulfuric acid / acetic acid / 1 h / 100 °C

3.1: sodium tetrahydroborate / ethanol / 5 h / 0 - 20 °C

4.1: triethylamine; dmap / dichloromethane / 144 h

5.1: pyridine / 0 - 4 °C

6.1: sodium azide; 15-crown-5; tetra(n-butyl)ammonium hydrogensulfate / N,N-dimethyl-formamide / 48 h / 100 °C

7.1: toluene-4-sulfonic acid / methanol; chloroform / 6 h

With pyridine; dmap; sodium tetrahydroborate; sodium azide; 15-crown-5; sulfuric acid; tetra(n-butyl)ammonium hydrogensulfate; toluene-4-sulfonic acid; triethylamine; acetyl chloride; In methanol; ethanol; dichloromethane; chloroform; acetic acid; N,N-dimethyl-formamide;

DOI:10.1021/ol4012053

upstream raw materials:

benzyl bromide

L-arabinofuranose

2,3,5-tri-O-benzyl-1-O-methyl-L-lyxofuranose

2,3,5-tri-O-benzyl-L-lyxitol

Downstream raw materials:

2,3,5-tri-O-benzyl-4-deoxy-4-azido-D-ribose

C₂₆H₂₇NO₃

C₃₆H₄₄N₂O₅

C₃₈H₄₆N₂O₅