tert-butyldimethylsilyl 2-azido-4-O-benzoyl-6-bromo-β-D-galactopyranoside

Base Information

• Chemical Name: tert-butyldimethylsilyl 2-azido-4-O-benzoyl-6-bromo-β-D-galactopyranoside
• CAS No.: 147158-37-0
• Molecular Formula: C₁₉H₂₈BrN₃O₅Si
• Molecular Weight: 486.438
• Mol file: 147158-37-0.mol

Synonyms:tert-butyldimethylsilyl 2-azido-4-O-benzoyl-6-bromo-β-D-galactopyranoside

Chemical Property of tert-butyldimethylsilyl 2-azido-4-O-benzoyl-6-bromo-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyldimethylsilyl 2-azido-4-O-benzoyl-6-bromo-β-D-galactopyranoside

There total 1 articles about tert-butyldimethylsilyl 2-azido-4-O-benzoyl-6-bromo-β-D-galactopyranoside 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: 87.0%

(tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside (147254-13-5) → tert-butyldimethylsilyl 2-azido-4-O-benzoyl-6-bromo-β-D-galactopyranoside (147158-37-0)

Guidance literature:

With Bromotrichloromethane; at 0 ℃; for 2.5h; Irradiation;

DOI:10.1021/ja00058a060 DOI:10.1021/ja00090a018

Reference yield: 100.0%

Benzyloxymethyl chloride (3587-60-8) + tert-butyldimethylsilyl 2-azido-4-O-benzoyl-6-bromo-β-D-galactopyranoside (147158-37-0) → tert-butyldimethylsilyl 2-azido-4-O-benzoyl-3-O-<(benzyloxy)methyl>-6-bromo-β-D-galactopyranoside (147158-38-1)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 15h; Heating;

DOI:10.1021/ja00058a060

Reference yield:

tert-butyldimethylsilyl 2-azido-4-O-benzoyl-6-bromo-β-D-galactopyranoside (147158-37-0) → C50H58N4O12SeSi (147158-39-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / diisopropylethylamine / CH₂Cl₂ / 15 h / Heating

2: 98 percent / triethylamine, benzeneselenol / 2.5 h / 60 °C

3: 1.) triethylamine, 2.) 1,8-diazabicyclo<5.4.0>undec-7-ene / 1.) dichloromethane, 0 deg C, 10 min, 2.) toluene, 100 deg C, 1.5 h

4: 95 percent / triethylamine / 1,2-dimethoxy-ethane / 10 h / 90 °C

5: triethylamine trihydrofluoride / acetonitrile / 6 h / 23 °C

6: 1.) 4-A molecular sieves, 2.) trifluoromethanesulfonic acid / 1.) toluene, 23 deg C, 2 h, 2.) toluene, -20 deg C

With trifluorormethanesulfonic acid; 4 A molecular sieve; triethylamine trihydrofluoride; Benzeneselenol; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; In 1,2-dimethoxyethane; dichloromethane; acetonitrile;

DOI:10.1021/ja00090a018

upstream raw materials:

(tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

Downstream raw materials:

tert-butyldimethylsilyl 2-azido-4-O-benzoyl-3-O-<(benzyloxy)methyl>-6-bromo-β-D-galactopyranoside

tunicamycin V

tert-butyldimethylsilyl 2-amino-4-O-benzoyl-3-O-<(benzyloxy)methyl>-6-bromo-β-D-galactopyranoside

tert-butyldimethylsilyl 4-O-benzoyl-3-O-<(benzyloxy)methyl>-6-bromo-2-phthalimido-β-D-galactopyranoside