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

Base Information

• Chemical Name: 3,5-O-(S)-benzylidene-6-cyano-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose
• CAS No.: 136839-37-7
• Molecular Formula: C₁₇H₁₉NO₅
• Molecular Weight: 317.342

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

Chemical Property of 3,5-O-(S)-benzylidene-6-cyano-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose

Chemical Property:

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Technology Process of 3,5-O-(S)-benzylidene-6-cyano-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose

There total 2 articles about 3,5-O-(S)-benzylidene-6-cyano-6-deoxy-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: 77.4%

3,5-O-(R)-benzylidene-6-cyano-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose (136839-36-6) → 3,5-O-(S)-benzylidene-6-cyano-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose (136839-37-7)

Guidance literature:

With aluminium trichloride; In diethyl ether; dichloromethane; at 21 ℃; for 0.5h;

DOI:10.1021/jo00025a033

Reference yield:

3,5-O-(S)-benzylidene-6-deoxy-6-iodo-1,2-O-isopropylidene-α-D-glucofuranose (111056-67-8) → 3,5-O-(S)-benzylidene-6-cyano-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose (136839-37-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / dimethylformamide / 2 h / 8 °C

2: 77.4 percent / AlCl₃ / diethyl ether; CH₂Cl₂ / 0.5 h / 21 °C

With aluminium trichloride; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00025a033

Reference yield: 99.0%

3,5-O-(S)-benzylidene-6-cyano-6-deoxy-1,2-O-isopropylidene-α-D-glucofuranose (136839-37-7) → 3,5-O-(S)-benzylidene-6-deoxy-1,2-O-isopropylidene-α-D-gluco-1,7-dialdehydohepto-1,4-furanose (136839-51-5)

Guidance literature:

With diisobutylaluminum hydride; In dichloromethane; at -40 ℃;

DOI:10.1021/jo00025a033

upstream raw materials:

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

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

Downstream raw materials:

3,5-O-(S)-benzylidene-6-deoxy-1,2-O-isopropylidene-α-D-gluco-1,7-dialdehydohepto-1,4-furanose

3,5-O-(S)-benzylidene-6,8,9-trideoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-non-8-yno-1,4-furanose

3,5-O-(R)-benzylidene-6,8,9-trideoxy-1,2-O-isopropylidene-α-L-glycero-D-gluco-non-8-yno-1,4-furanose

3,5-O-(S)-benzylidene-6,8,9-trideoxy-1,2-O-isopropylidene-7-(4-nitrobenzoyl)-α-D-glycero-D-gluco-non-8-yno-1,4-furanose

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