3,5-O-benzylidene-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose

Base Information

• Chemical Name: 3,5-O-benzylidene-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose
• CAS No.: 110920-93-9
• Molecular Formula: C₃₂H₃₈O₆Si
• Molecular Weight: 546.736
• Mol file: 110920-93-9.mol

Synonyms:3,5-O-benzylidene-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose

Chemical Property of 3,5-O-benzylidene-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,5-O-benzylidene-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose

There total 11 articles about 3,5-O-benzylidene-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose 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: 94.4%

benzaldehyde (100-52-7) + (3aR,5R,6S,6aR)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2,2-dimethyltetrahydrofuro(3,2-d)(1,3)dioxol-6-ol (110920-92-8) → 3,5-O-benzylidene-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose (110920-93-9)

Guidance literature:

With zinc(II) chloride; for 22h; Ambient temperature;

DOI:10.1016/0008-6215(92)80042-Y

Reference yield: 91.0%

Benzaldehyde dipent-4-enyl acetal (2031-48-3) + (3aR,5R,6S,6aR)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2,2-dimethyltetrahydrofuro(3,2-d)(1,3)dioxol-6-ol (110920-92-8) → 3,5-O-benzylidene-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose (110920-93-9)

Guidance literature:

With N-Bromosuccinimide; triethylsilyl trifluoromethyl sulfonate; In acetonitrile; for 0.0833333h; Ambient temperature;

DOI:10.1039/c39940000749

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) + (3aR,5R,6S,6aR)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2,2-dimethyltetrahydrofuro(3,2-d)(1,3)dioxol-6-ol (110920-92-8) → 3,5-O-(R)-benzylidene-6-O-(tert-butyldiphenylsilyl)-1,2-O-isopropylidene-α-D-glucofuranose (110920-93-9)

Guidance literature:

With pyridinium p-toluenesulfonate; In dichloromethane; at 40 ℃; for 2h; Yield given;

DOI:10.1016/0008-6215(86)84012-5

upstream raw materials:

Benzaldehyde dipent-4-enyl acetal

(3aR,5R,6S,6aR)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2,2-dimethyltetrahydrofuro(3,2-d)(1,3)dioxol-6-ol

benzaldehyde

tert-butylchlorodiphenylsilane

Downstream raw materials:

3,5-O-(R)-benzylidene-6-deoxy-6-iodo-1,2-O-isopropylidene-α-D-glucofuranose

3,5-O-(S)-benzylidene-6-deoxy-6-iodo-1,2-O-isopropylidene-α-D-glucofuranose

3,5-O-(S)-benzylidene-1,2-O-isopropylidene-α-D-glucofuranose

3,5-O-(R)-benzylidene-1,2-O-isopropylidene-α-D-glucofuranose