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

Base Information

• Chemical Name: benzoyl 6-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-α-D-mannofuranoside
• CAS No.: 328533-51-3
• Molecular Formula: C₂₂H₃₄O₇Si
• Molecular Weight: 438.593

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

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

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

There total 1 articles about benzoyl 6-O-(tert-butyldimethylsilyl)-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: 91.0%

1-O-benzoyl-2,3-O-isopropylidene-α-D-mannofuranoside (57492-90-7) + tert-butyldimethylsilyl chloride (18162-48-6) → benzoyl 6-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-α-D-mannofuranoside (328533-51-3)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

DOI:10.1021/jo0057452

Reference yield: 98.0%

methanesulfonyl chloride (124-63-0) + benzoyl 6-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-α-D-mannofuranoside (328533-51-3) → C23H36O9SSi (1201435-96-2)

Guidance literature:

With triethylamine; In dichloromethane; for 3h;

DOI:10.1016/j.tetlet.2009.09.139

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

upstream raw materials:

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

tert-butyldimethylsilyl chloride

Downstream 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

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

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

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

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