5-azido-6-O-benzoyl-3-O-benzyl-1-O-tert-butyldimethylsilyl-5-deoxy-L-iditol

Base Information

• Chemical Name: 5-azido-6-O-benzoyl-3-O-benzyl-1-O-tert-butyldimethylsilyl-5-deoxy-L-iditol
• CAS No.: 92812-61-8
• Molecular Formula: C₂₆H₃₇N₃O₆Si
• Molecular Weight: 515.682
• Mol file: 92812-61-8.mol

Synonyms:5-azido-6-O-benzoyl-3-O-benzyl-1-O-tert-butyldimethylsilyl-5-deoxy-L-iditol

Chemical Property of 5-azido-6-O-benzoyl-3-O-benzyl-1-O-tert-butyldimethylsilyl-5-deoxy-L-iditol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-azido-6-O-benzoyl-3-O-benzyl-1-O-tert-butyldimethylsilyl-5-deoxy-L-iditol

There total 5 articles about 5-azido-6-O-benzoyl-3-O-benzyl-1-O-tert-butyldimethylsilyl-5-deoxy-L-iditol 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: 90.0%

tert-butyldimethylsilyl chloride (18162-48-6) + 5-azido-6-O-benzoyl-3-O-benzyl-5-deoxy-L-iditol (92840-96-5) → 5-azido-6-O-benzoyl-3-O-benzyl-1-O-tert-butyldimethylsilyl-5-deoxy-L-iditol (92812-61-8)

Guidance literature:

With pyridine; In 1,2-dichloro-ethane; at 37 ℃; for 17h;

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) → 5-azido-6-O-benzoyl-3-O-benzyl-1-O-tert-butyldimethylsilyl-5-deoxy-L-iditol (92812-61-8)

Guidance literature:

Multi-step reaction with 5 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

With pyridine; sodium tetrahydroborate; sodium azide; sulfuric acid; In 1,4-dioxane; 1,2-dimethoxyethane; 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-1,2-O-isopropylidene-β-L-idofuranose (92812-59-4) → 5-azido-6-O-benzoyl-3-O-benzyl-1-O-tert-butyldimethylsilyl-5-deoxy-L-iditol (92812-61-8)

Guidance literature:

Multi-step reaction with 3 steps

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

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

3: 90 percent / pyridine / 1,2-dichloro-ethane / 17 h / 37 °C

With pyridine; sodium tetrahydroborate; sulfuric acid; In 1,4-dioxane; 1,2-dimethoxyethane; 1,2-dichloro-ethane;

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

upstream raw materials:

tert-butyldimethylsilyl chloride

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

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

5-azido-6-O-benzoyl-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose

Downstream raw materials:

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

methyl 2,6-diazido-4-O-benzyl-2,6-dideoxy-α-L-idopyranoside

methyl 2,6-diazido-4-O-benzyl-2,6-dideoxy-β-L-idopyranoside

Benzoic acid (S)-2-azido-2-((4R,5S,6S)-5-benzyloxy-2,2-dimethyl-6-trifluoromethanesulfonyloxymethyl-[1,3]dioxan-4-yl)-ethyl ester