2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate

Base Information

• Chemical Name: 2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate
• CAS No.: 154920-28-2
• Molecular Formula: C₂₈H₃₇Cl₃N₄O₅Si
• Molecular Weight: 644.07
• Mol file: 154920-28-2.mol

Synonyms:2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate

Chemical Property of 2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate

There total 20 articles about 2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate 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: 91.0%

trichloroacetonitrile (545-06-2) + 2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-β-D-glucopyranose → 2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate (154920-28-2)

Guidance literature:

With potassium carbonate; In dichloromethane; at 25 ℃; for 1.75h;

DOI:10.1002/(SICI)1099-0690(200004)2000:8<1547::AID-EJOC1547<3.0.CO;2-C

Reference yield:

tert-butyldimethylsilyl 2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-β-D-glucopyranoside (154920-34-0) → 2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate (154920-28-2)

Guidance literature:

Multi-step reaction with 2 steps

1: glacial AcOH; TBAF / tetrahydrofuran / 0.5 h

2: 87.5 mg / DBU / CH₂Cl₂ / 1 h / 0 °C

With tetrabutyl ammonium fluoride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; dichloromethane;

DOI:10.1002/chem.200390009

Reference yield:

tert-Butyldimethylsilyl-2-azido-2-desoxy-β-D-glucopyranosid (99049-67-9) → 2-azido-3,6-di-O-benzyl-4-O-tert-butyldimethylsilyl-2-deoxy-α/β-D-glucopyranosyl trichloroacetimidate (154920-28-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 29.0 g / p-TsOH*H₂O / acetonitrile / 20 °C

2: 95 percent / molecular sieves 4 Angstroem; Ag₂O / CH₂Cl₂ / 8 h

3: 85 percent / triethylsilane; TFA / CH₂Cl₂ / 5 h / 20 °C

4: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 20 °C

5: glacial AcOH; TBAF / tetrahydrofuran / 0.5 h

6: 87.5 mg / DBU / CH₂Cl₂ / 1 h / 0 °C

With 2,6-dimethylpyridine; triethylsilane; 4 A molecular sieve; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; trifluoroacetic acid; silver(l) oxide; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1002/chem.200390009

upstream raw materials:

trichloroacetonitrile

tert-Butyldimethylsilyl-2-azido-2-desoxy-β-D-glucopyranosid

tert-Butyldimethylsilyl-2-azido-3,6-di-O-benzyl-2-desoxy-β-D-glucopyranosid

tert-Butyldimethylsilyl-3,4,6-tri-O-acetyl-2-azido-2-desoxy-β-D-glucopyranosid