benzoyl 5-azido-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside

Base Information

Chemical Name:benzoyl 5-azido-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside
CAS No.:328533-62-6
Molecular Formula:C₂₂H₃₃N₃O₆Si
Molecular Weight:463.606
Hs Code.:

Synonyms:benzoyl 5-azido-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside

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Chemical Property of benzoyl 5-azido-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside

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Technology Process of benzoyl 5-azido-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside

There total 6 articles about benzoyl 5-azido-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside 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: 86.0%

: 328533-75-1
Benzoic acid (3aS,4R,6S,6aS)-6-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-1-methanesulfonyloxy-ethyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester

: 328533-62-6
benzoyl 5-azido-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 80 ℃; for 11h;
DOI:10.1021/jo0057452

Reference yield:

: 57492-90-7
1-O-benzoyl-2,3-O-isopropylidene-α-D-mannofuranoside

: 328533-62-6
benzoyl 5-azido-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 91 percent / imidazole / dimethylformamide / 0.5 h / 20 °C

2.1: diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 3 h / 0 °C

2.2: 73 percent / tetrahydrofuran

3.1: 83 percent / NaHCO₃ / methanol; H₂O / 2 h / 20 °C

4.1: pyridine / 0.75 h / 0 °C

5.1: 86 percent / NaN₃ / dimethylformamide / 11 h / 80 °C

With pyridine; 1H-imidazole; sodium azide; di-isopropyl azodicarboxylate; sodium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;
DOI:10.1021/jo0057452

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 328533-62-6
benzoyl 5-azido-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 91 percent / imidazole / dimethylformamide / 0.5 h / 20 °C

2.1: diisopropyl azodicarboxylate; triphenylphosphine / tetrahydrofuran / 3 h / 0 °C

2.2: 73 percent / tetrahydrofuran

3.1: 83 percent / NaHCO₃ / methanol; H₂O / 2 h / 20 °C

4.1: pyridine / 0.75 h / 0 °C

5.1: 86 percent / NaN₃ / dimethylformamide / 11 h / 80 °C

With pyridine; 1H-imidazole; sodium azide; di-isopropyl azodicarboxylate; sodium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;
DOI:10.1021/jo0057452