benzoyl 5-azido-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3,-O-isopropylidene-β-L-gulofuranoside

Base Information

• Chemical Name: benzoyl 5-azido-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3,-O-isopropylidene-β-L-gulofuranoside
• CAS No.: 328533-57-9
• Molecular Formula: C₂₂H₃₃N₃O₆Si
• Molecular Weight: 463.606

Synonyms:benzoyl 5-azido-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3,-O-isopropylidene-β-L-gulofuranoside

Chemical Property of benzoyl 5-azido-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3,-O-isopropylidene-β-L-gulofuranoside

Chemical Property:

Purity/Quality:

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Technology Process of benzoyl 5-azido-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3,-O-isopropylidene-β-L-gulofuranoside

There total 4 articles about benzoyl 5-azido-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3,-O-isopropylidene-β-L-gulofuranoside 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%

Benzoic acid (3aS,4R,6S,6aS)-6-[(R)-2-(tert-butyl-dimethyl-silanyloxy)-1-trifluoromethanesulfonyloxy-ethyl]-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester (328533-74-0) → benzoyl 5-azido-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3,-O-isopropylidene-β-L-gulofuranoside (328533-57-9)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

DOI:10.1021/jo0057452

Reference yield:

1-O-benzoyl-2,3-O-isopropylidene-α-D-mannofuranoside (57492-90-7) → benzoyl 5-azido-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3,-O-isopropylidene-β-L-gulofuranoside (328533-57-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / imidazole / dimethylformamide / 0.5 h / 20 °C

2: 90 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

3: 87 percent / NaN₃ / dimethylformamide / 2 h / 20 °C

With pyridine; 1H-imidazole; sodium azide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo0057452

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → benzoyl 5-azido-6-O-(tert-butyldimethylsilyl)-5-deoxy-2,3,-O-isopropylidene-β-L-gulofuranoside (328533-57-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 91 percent / imidazole / dimethylformamide / 0.5 h / 20 °C

2: 90 percent / pyridine / CH₂Cl₂ / 0.5 h / 0 °C

3: 87 percent / NaN₃ / dimethylformamide / 2 h / 20 °C

With pyridine; 1H-imidazole; sodium azide; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo0057452

upstream raw materials:

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

1-O-benzoyl-2,3-O-isopropylidene-α-D-mannofuranoside

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

1-O-benzoyl-5-[(N',N''-di-tert-butoxycarbonyl)guanidino]-6-O-tert-butyldimetylsilyl-5-deoxy-2,3-O-isopropylidene-β-L-gulofuranose

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