3-O-acetyl-2,6-diazido-4-O-benzyl-2,6-dideoxy-L-idopyranosyl chloride

Base Information

• Chemical Name: 3-O-acetyl-2,6-diazido-4-O-benzyl-2,6-dideoxy-L-idopyranosyl chloride
• CAS No.: 115225-34-8
• Molecular Formula: C₁₅H₁₇ClN₆O₄
• Molecular Weight: 380.791
• Mol file: 115225-34-8.mol

Synonyms:3-O-acetyl-2,6-diazido-4-O-benzyl-2,6-dideoxy-L-idopyranosyl chloride

Chemical Property of 3-O-acetyl-2,6-diazido-4-O-benzyl-2,6-dideoxy-L-idopyranosyl chloride

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-O-acetyl-2,6-diazido-4-O-benzyl-2,6-dideoxy-L-idopyranosyl chloride

There total 13 articles about 3-O-acetyl-2,6-diazido-4-O-benzyl-2,6-dideoxy-L-idopyranosyl chloride 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: 80.0%

1,3-di-O-acetyl-2,6-diazido-4-O-benzyl-2,6-dideoxy-L-idopyranose → 3-O-acetyl-2,6-diazido-4-O-benzyl-2,6-dideoxy-L-idopyranosyl chloride (115225-34-8)

Guidance literature:

With hydrogenchloride; In diethyl ether; Ambient temperature;

DOI:10.1016/0008-6215(84)85278-7

Reference yield:

6-O-Benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose (37776-15-1) → 3-O-acetyl-2,6-diazido-4-O-benzyl-2,6-dideoxy-L-idopyranosyl chloride (115225-34-8)

Guidance literature:

Multi-step reaction with 13 steps

1: pyridine / 1,2-dichloro-ethane / 1 h / 0 °C

2: sodium azide / dimethylformamide / 1 h / 70 °C

3: 93 percent / 1 M aqu. sulfuric acid / dioxane / 5 h / 80 °C

4: 81 percent / sodium borohydride / 1,2-dimethoxy-ethane / 1 h / 0 °C

5: 90 percent / pyridine / 1,2-dichloro-ethane / 17 h / 37 °C

6: 99 percent / pyridinium p-toluenesulfonate / 1,2-dichloro-ethane / 2 h / 60 °C

7: 87 percent / tetrabutylammonium fluoride / various solvent(s) / 1 h / 0 °C

8: pyridine / 1,2-dichloro-ethane / 0.25 h / 0 °C

9: sodium azide / dimethylformamide / 0.5 h / Ambient temperature

10: 95 percent / 2 M sodium methoxide / methanol / 2 h / Ambient temperature

11: 1.) pyridine, pyridine trifluoroacetate, dicyclohexylcarbodiimide, 2.) 80 mM sulfuric acid / 1.) dimethyl sulfoxide/benzene, 1 h, room temperature, 2.) water/1,4-dioxane, 70 deg C, 1.5 h

12: 95 percent / pyridine / 2.5 h / Ambient temperature

13: 80 percent / hydrogen chloride / diethyl ether / Ambient temperature

With pyridine; hydrogenchloride; sodium tetrahydroborate; sodium azide; sulfuric acid; tetrabutyl ammonium fluoride; sodium methylate; pyridinium trifluroacetate; pyridinium p-toluenesulfonate; dicyclohexyl-carbodiimide; In 1,4-dioxane; methanol; 1,2-dimethoxyethane; diethyl ether; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(84)85278-7

Reference yield:

5-azido-6-O-benzoyl-3-O-benzyl-5-deoxy-L-iditol (92840-96-5) → 3-O-acetyl-2,6-diazido-4-O-benzyl-2,6-dideoxy-L-idopyranosyl chloride (115225-34-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 90 percent / pyridine / 1,2-dichloro-ethane / 17 h / 37 °C

2: 99 percent / pyridinium p-toluenesulfonate / 1,2-dichloro-ethane / 2 h / 60 °C

3: 87 percent / tetrabutylammonium fluoride / various solvent(s) / 1 h / 0 °C

4: pyridine / 1,2-dichloro-ethane / 0.25 h / 0 °C

5: sodium azide / dimethylformamide / 0.5 h / Ambient temperature

6: 95 percent / 2 M sodium methoxide / methanol / 2 h / Ambient temperature

7: 1.) pyridine, pyridine trifluoroacetate, dicyclohexylcarbodiimide, 2.) 80 mM sulfuric acid / 1.) dimethyl sulfoxide/benzene, 1 h, room temperature, 2.) water/1,4-dioxane, 70 deg C, 1.5 h

8: 95 percent / pyridine / 2.5 h / Ambient temperature

9: 80 percent / hydrogen chloride / diethyl ether / Ambient temperature

With pyridine; hydrogenchloride; sodium azide; sulfuric acid; tetrabutyl ammonium fluoride; sodium methylate; pyridinium trifluroacetate; pyridinium p-toluenesulfonate; dicyclohexyl-carbodiimide; In methanol; diethyl ether; 1,2-dichloro-ethane; N,N-dimethyl-formamide;

DOI:10.1016/0008-6215(84)85278-7

upstream raw materials:

6-O-Benzoyl-3-O-benzyl-1,2-O-isopropylidene-α-D-glucofuranose

1,5-diazido-3-O-benzyl-1,5-dideoxy-2,4-O-isopropylidene-L-iditol

5-azido-6-O-benzoyl-3-O-benzyl-5-deoxy-L-iditol

5-azido-6-O-benzoyl-3-O-benzyl-5-deoxy-2,4-O-isopropylidene-L-iditol

Downstream raw materials:

3-O-(3-O-acetyl-2,6-diazido-4-O-benzyl-2,6-dideoxy-β-L-idopyranosyl)-5-O-benzoyl-1,2-O-isopropylidene-β-D-ribofuranose