6-O-(3'',4''-diazido-2'',6''-di-O-benzyl-3'',4''-dideoxy-α-D-glucopyranosyl)-1,3,2',6'-tetraazidoneamine

Base Information

• Chemical Name: 6-O-(3'',4''-diazido-2'',6''-di-O-benzyl-3'',4''-dideoxy-α-D-glucopyranosyl)-1,3,2',6'-tetraazidoneamine
• CAS No.: 688744-79-8
• Molecular Formula: C₃₂H₃₈N₁₈O₉
• Molecular Weight: 818.769
• Mol file: 688744-79-8.mol

Synonyms:

Chemical Property of 6-O-(3'',4''-diazido-2'',6''-di-O-benzyl-3'',4''-dideoxy-α-D-glucopyranosyl)-1,3,2',6'-tetraazidoneamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-O-(3'',4''-diazido-2'',6''-di-O-benzyl-3'',4''-dideoxy-α-D-glucopyranosyl)-1,3,2',6'-tetraazidoneamine

There total 5 articles about 6-O-(3'',4''-diazido-2'',6''-di-O-benzyl-3'',4''-dideoxy-α-D-glucopyranosyl)-1,3,2',6'-tetraazidoneamine 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:

neamine tetrahydrochloride (15446-43-2) → 6-O-(3'',4''-diazido-2'',6''-di-O-benzyl-3'',4''-dideoxy-α-D-glucopyranosyl)-1,3,2',6'-tetraazidoneamine (688744-79-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 74 percent / TfN₃; CuSO₄ / H₂O; CH₂Cl₂

2: 41 percent / p-toluenesulfonic acid monohydrate / acetonitrile / 20 °C

3: DMAP; Et₃N / CH₂Cl₂ / 20 °C

4: 44 g / acetic acid / dioxane; H₂O / 60 - 65 °C

5: N-iodosuccinimide; trifluoromethanesulfonic acid / diethyl ether; CH₂Cl₂ / 4 h

6: NaOMe / methanol; tetrahydrofuran / 2 h / 20 °C

With dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; triflic azide; sodium methylate; toluene-4-sulfonic acid; copper(II) sulfate; acetic acid; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; acetonitrile;

DOI:10.1021/ol0497685

Reference yield:

1,3,2′,6′-tetraazidoneamine (671809-10-2) → 6-O-(3'',4''-diazido-2'',6''-di-O-benzyl-3'',4''-dideoxy-α-D-glucopyranosyl)-1,3,2',6'-tetraazidoneamine (688744-79-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 41 percent / p-toluenesulfonic acid monohydrate / acetonitrile / 20 °C

2: DMAP; Et₃N / CH₂Cl₂ / 20 °C

3: 44 g / acetic acid / dioxane; H₂O / 60 - 65 °C

4: N-iodosuccinimide; trifluoromethanesulfonic acid / diethyl ether; CH₂Cl₂ / 4 h

5: NaOMe / methanol; tetrahydrofuran / 2 h / 20 °C

With dmap; N-iodo-succinimide; trifluorormethanesulfonic acid; sodium methylate; toluene-4-sulfonic acid; acetic acid; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; water; acetonitrile;

DOI:10.1021/ol0497685

Reference yield:

1,3,2',6'-tetraazido-3',4'-di-O-acetylneamine (688744-66-3) → 6-O-(3'',4''-diazido-2'',6''-di-O-benzyl-3'',4''-dideoxy-α-D-glucopyranosyl)-1,3,2',6'-tetraazidoneamine (688744-79-8)

Guidance literature:

Multi-step reaction with 2 steps

1: N-iodosuccinimide; trifluoromethanesulfonic acid / diethyl ether; CH₂Cl₂ / 4 h

2: NaOMe / methanol; tetrahydrofuran / 2 h / 20 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; sodium methylate; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/ol0497685

upstream raw materials:

neamine tetrahydrochloride

1,3,2′,6′-tetraazidoneamine

1,3,2',6'-tetraazido-3',4'-di-O-acetylneamine

1,3,2’,6’-tetrazido-5,6-O-cyclohexylidene neamine