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

Base Information

Chemical Name:tert-butyldimethylsilyl 4-O-benzoyl-3-O-<(benzyloxy)methyl>-6-bromo-2-phthalimido-β-D-galactopyranoside
CAS No.:158421-19-3
Molecular Formula:C₃₅H₄₀BrNO₈Si
Molecular Weight:710.694
Hs Code.:

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

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

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

There total 5 articles about tert-butyldimethylsilyl 4-O-benzoyl-3-O-<(benzyloxy)methyl>-6-bromo-2-phthalimido-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:

: 3587-60-8
Benzyloxymethyl chloride

: 158421-19-3
tert-butyldimethylsilyl 4-O-benzoyl-3-O-<(benzyloxy)methyl>-6-bromo-2-phthalimido-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 3 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

With Benzeneselenol; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1021/ja00090a018

Reference yield:

: 147254-13-5
(tert-butyldimethyl)silyl 2-azido-4,6-O-benzylidene-2-deoxy-β-D-galactopyranoside

: 158421-19-3
tert-butyldimethylsilyl 4-O-benzoyl-3-O-<(benzyloxy)methyl>-6-bromo-2-phthalimido-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 87 percent / bromotrichloromethane / 2.5 h / 0 °C / Irradiation

2: 89 percent / diisopropylethylamine / CH₂Cl₂ / 15 h / Heating

3: 98 percent / triethylamine, benzeneselenol / 2.5 h / 60 °C

4: 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

With Bromotrichloromethane; Benzeneselenol; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1021/ja00090a018

Reference yield:

: 147158-37-0
tert-butyldimethylsilyl 2-azido-4-O-benzoyl-6-bromo-β-D-galactopyranoside

: 158421-19-3
tert-butyldimethylsilyl 4-O-benzoyl-3-O-<(benzyloxy)methyl>-6-bromo-2-phthalimido-β-D-galactopyranoside

Guidance literature:: Multi-step reaction with 3 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

With Benzeneselenol; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane;
DOI:10.1021/ja00090a018