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

Base Information

• Chemical Name: benzoyl 6-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-5-O-methyl-α-D-mannofuranoside
• CAS No.: 328533-52-4
• Molecular Formula: C₂₃H₃₆O₇Si
• Molecular Weight: 452.62

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

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

Chemical Property:

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

There total 3 articles about benzoyl 6-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-5-O-methyl-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: 93.0%

benzoyl 6-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-α-D-mannofuranoside (328533-51-3) + methyl iodide (74-88-4) → benzoyl 6-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-5-O-methyl-α-D-mannofuranoside (328533-52-4)

Guidance literature:

With silver(l) oxide; In acetone; at 20 ℃; for 24h;

DOI:10.1021/jo0057452

Reference yield:

1-O-benzoyl-2,3-O-isopropylidene-α-D-mannofuranoside (57492-90-7) → benzoyl 6-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-5-O-methyl-α-D-mannofuranoside (328533-52-4)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 93 percent / Ag₂O / acetone / 24 h / 20 °C

With 1H-imidazole; silver(l) oxide; In N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo0057452

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → benzoyl 6-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-5-O-methyl-α-D-mannofuranoside (328533-52-4)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 93 percent / Ag₂O / acetone / 24 h / 20 °C

With 1H-imidazole; silver(l) oxide; In N,N-dimethyl-formamide; acetone;

DOI:10.1021/jo0057452

upstream raw materials:

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

methyl iodide

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

tert-butyldimethylsilyl chloride

Downstream raw materials:

benzoyl 2,3-O-isopropylidene-5-methyl-α-D-mannofuranoside

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

Benzoic acid (3aS,4R,6R,6aS)-6-((R)-2-methanesulfonyloxy-1-methoxy-ethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl ester

benzoyl 6-azido-6-deoxy-2,3-O-isopropylidene-5-O-methyl-α-D-mannofuranoside

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