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

Base Information

Chemical Name:benzoyl 5-(tert-butoxycarbonyl)amino-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside
CAS No.:328533-63-7
Molecular Formula:C₂₇H₄₃NO₈Si
Molecular Weight:537.726
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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

There total 7 articles about benzoyl 5-(tert-butoxycarbonyl)amino-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:

: 24424-99-5
di-tert-butyl dicarbonate

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

: 328533-63-7
benzoyl 5-(tert-butoxycarbonyl)amino-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside

Guidance literature:: With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 1h;
DOI:10.1021/jo0057452

Reference yield:

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

: 328533-63-7
benzoyl 5-(tert-butoxycarbonyl)amino-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside

Guidance literature:: Multi-step reaction with 6 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

6.1: 140 mg / H₂ / Pd/C / ethyl acetate / 1 h / 20 °C

With pyridine; 1H-imidazole; sodium azide; di-isopropyl azodicarboxylate; hydrogen; sodium hydrogencarbonate; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo0057452

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 328533-63-7
benzoyl 5-(tert-butoxycarbonyl)amino-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3-O-isopropylidene-α-D-mannofuranoside

Guidance literature:: Multi-step reaction with 6 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

6.1: 140 mg / H₂ / Pd/C / ethyl acetate / 1 h / 20 °C

With pyridine; 1H-imidazole; sodium azide; di-isopropyl azodicarboxylate; hydrogen; sodium hydrogencarbonate; triphenylphosphine; palladium on activated charcoal; In tetrahydrofuran; methanol; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo0057452