3-azido-4-O-(tert-butyldiMethylsilyl)-3,6-dideoxy-α-D-glucopyranose 1,2-diacetate

Base Information

• Chemical Name: 3-azido-4-O-(tert-butyldiMethylsilyl)-3,6-dideoxy-α-D-glucopyranose 1,2-diacetate
• CAS No.: 107599-49-5
• Molecular Formula: C16H29N3O6Si
• Molecular Weight: 387.50300
• Mol file: 107599-49-5.mol

Synonyms:3-azido-4-O-(tert-butyldiMethylsilyl)-3,6-dideoxy-α-D-glucopyranose 1,2-diacetate;

Chemical Property of 3-azido-4-O-(tert-butyldiMethylsilyl)-3,6-dideoxy-α-D-glucopyranose 1,2-diacetate

Chemical Property:

• PSA: 120.81000
• LogP: 2.74806

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-azido-4-O-(tert-butyldiMethylsilyl)-3,6-dideoxy-α-D-glucopyranose 1,2-diacetate

There total 16 articles about 3-azido-4-O-(tert-butyldiMethylsilyl)-3,6-dideoxy-α-D-glucopyranose 1,2-diacetate 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%

acetic anhydride (108-24-7) + methyl 3-azido-4-O-(tert-butyldimethylsilyl)-3,6-dideoxy-α-D-glucopyranoside 2-acetate (107599-48-4) → 3-azido-4-O-(tert-butyldimethylsilyl)-3,6-dideoxy-α-D-glucopyranose 1,2-diacetate (107599-49-5)

Guidance literature:

sulfuric acid; at 0 - 25 ℃; for 2h;

DOI:10.1021/ja00243a043

Reference yield: 90.0%

methyl 3-azido-4-O-(tert-butyldimethylsilyl)-3,6-dideoxy-α-D-glucopyranoside 2-acetate (107599-48-4) + 3-(acetylamino)-3,6-dideoxy-2,4-bis-O-<(1,1-dimethylethyl)dimethylsilyl>-α-D-mannopyranoside acetate → 3-azido-4-O-(tert-butyldimethylsilyl)-3,6-dideoxy-α-D-glucopyranose 1,2-diacetate (107599-49-5)

Guidance literature:

sulfuric acid; for 2h; Ambient temperature;

DOI:10.1021/ja00222a030

Reference yield:

methyl 4-O-(tert-butyldimethylsilyl)-6-deoxy-α-D-allopyranoside 2-acetate (107599-46-2) → 3-azido-4-O-(tert-butyldimethylsilyl)-3,6-dideoxy-α-D-glucopyranose 1,2-diacetate (107599-49-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / pyridine / CH₂Cl₂ / 2 h / 25 °C

2: 83 percent / NaN₃, 15-crown-5 / dimethylformamide / 0.5 h / 25 °C

3: 90 percent / H₂SO₄ / 2 h / 0 - 25 °C

With pyridine; sodium azide; 15-crown-5; sulfuric acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ja00243a043

upstream raw materials:

acetic anhydride

methyl 3-azido-4-O-(tert-butyldimethylsilyl)-3,6-dideoxy-α-D-glucopyranoside 2-acetate

methyl 2-O-acetyl-4,6-O-benzylidene-α,D-glucopyranoside

methyl (R)-4,6-O-benzylidene-α-D-ribo-hexopyranosid-3-ulose acetate