tert-butyldimethylsilyl 4-O-benzoyl-3-O-[(benzyloxy)methyl]-2,6-dideoxy-6-bromo-2-phthalimido-β-D-glucopyranoside

Base Information

Chemical Name:tert-butyldimethylsilyl 4-O-benzoyl-3-O-[(benzyloxy)methyl]-2,6-dideoxy-6-bromo-2-phthalimido-β-D-glucopyranoside
CAS No.:459170-38-8
Molecular Formula:C₃₅H₄₀BrNO₈Si
Molecular Weight:710.694
Hs Code.:

Synonyms:tert-butyldimethylsilyl 4-O-benzoyl-3-O-[(benzyloxy)methyl]-2,6-dideoxy-6-bromo-2-phthalimido-β-D-glucopyranoside

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Chemical Property of tert-butyldimethylsilyl 4-O-benzoyl-3-O-[(benzyloxy)methyl]-2,6-dideoxy-6-bromo-2-phthalimido-β-D-glucopyranoside

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Technology Process of tert-butyldimethylsilyl 4-O-benzoyl-3-O-[(benzyloxy)methyl]-2,6-dideoxy-6-bromo-2-phthalimido-β-D-glucopyranoside

There total 6 articles about tert-butyldimethylsilyl 4-O-benzoyl-3-O-[(benzyloxy)methyl]-2,6-dideoxy-6-bromo-2-phthalimido-β-D-glucopyranoside 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:

: 10022-13-6
1,3,4,6-tetra-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranose

: 459170-38-8
tert-butyldimethylsilyl 4-O-benzoyl-3-O-[(benzyloxy)methyl]-2,6-dideoxy-6-bromo-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: ethylenediamine; AcOH / tetrahydrofuran / 6 h

2: 82 percent / imidazole / dimethylformamide / 47 h / 0 - 20 °C

3: 2.96 percent / NaOMe; MeOH / 2.5 h / 20 °C

4: 3.03 g / TsOH*H₂O / acetonitrile / 13.5 h

5: NBS; BaCO₃ / CCl₄ / 1 h / Heating

6: 3.24 g / DIEA / tetrahydrofuran / 27.5 h / Heating

With 1H-imidazole; methanol; N-Bromosuccinimide; sodium methylate; toluene-4-sulfonic acid; acetic acid; ethylenediamine; N-ethyl-N,N-diisopropylamine; barium carbonate; In tetrahydrofuran; tetrachloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja0127234

Reference yield:

: 72858-55-0,90405-21-3,90405-42-8,124362-60-3,144221-86-3
3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-D-glucopyranose

: 459170-38-8
tert-butyldimethylsilyl 4-O-benzoyl-3-O-[(benzyloxy)methyl]-2,6-dideoxy-6-bromo-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 82 percent / imidazole / dimethylformamide / 47 h / 0 - 20 °C

2: 2.96 percent / NaOMe; MeOH / 2.5 h / 20 °C

3: 3.03 g / TsOH*H₂O / acetonitrile / 13.5 h

4: NBS; BaCO₃ / CCl₄ / 1 h / Heating

5: 3.24 g / DIEA / tetrahydrofuran / 27.5 h / Heating

With 1H-imidazole; methanol; N-Bromosuccinimide; sodium methylate; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; barium carbonate; In tetrahydrofuran; tetrachloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/ja0127234

Reference yield:

: 732246-93-4
(tert-butyl)dimethylsilyl 2-deoxy-2-phthalimido-β-D-glucopyranoside

: 459170-38-8
tert-butyldimethylsilyl 4-O-benzoyl-3-O-[(benzyloxy)methyl]-2,6-dideoxy-6-bromo-2-phthalimido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 3.03 g / TsOH*H₂O / acetonitrile / 13.5 h

2: NBS; BaCO₃ / CCl₄ / 1 h / Heating

3: 3.24 g / DIEA / tetrahydrofuran / 27.5 h / Heating

With N-Bromosuccinimide; toluene-4-sulfonic acid; N-ethyl-N,N-diisopropylamine; barium carbonate; In tetrahydrofuran; tetrachloromethane; acetonitrile;
DOI:10.1021/ja0127234