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

Base Information

Chemical Name:3,5-O-(S)-benzylidene-6,8,9-trideoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-non-8-yno-1,4-furanose
CAS No.:136839-30-0
Molecular Formula:C₁₉H₂₂O₆
Molecular Weight:346.38
Hs Code.:

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

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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

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

There total 5 articles about 3,5-O-(S)-benzylidene-6,8,9-trideoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-non-8-yno-1,4-furanose 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: 42.0%

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

: 74-86-2,25067-58-7
acetylene

: 136839-30-0
3,5-O-(S)-benzylidene-6,8,9-trideoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-non-8-yno-1,4-furanose

: 136846-43-0
3,5-O-(R)-benzylidene-6,8,9-trideoxy-1,2-O-isopropylidene-α-L-glycero-D-gluco-non-8-yno-1,4-furanose

Guidance literature:: With ethylmagnesium bromide; In tetrahydrofuran; at -10 ℃;
DOI:10.1021/jo00025a033

Reference yield: 32.0%

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

: 74-86-2,25067-58-7
acetylene

: 136839-30-0
3,5-O-(S)-benzylidene-6,8,9-trideoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-non-8-yno-1,4-furanose

: 136846-43-0
3,5-O-(R)-benzylidene-6,8,9-trideoxy-1,2-O-isopropylidene-α-L-glycero-D-gluco-non-8-yno-1,4-furanose

Guidance literature:: With ethylmagnesium bromide; In tetrahydrofuran; at -10 ℃;
DOI:10.1021/jo00025a033

Reference yield:

: 111056-67-8
3,5-O-(S)-benzylidene-6-deoxy-6-iodo-1,2-O-isopropylidene-α-D-glucofuranose

: 136839-30-0
3,5-O-(S)-benzylidene-6,8,9-trideoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-non-8-yno-1,4-furanose

Guidance literature:: Multi-step reaction with 4 steps

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

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

3: 99 percent / di(isobutyl)aluminum hydride / CH₂Cl₂ / -40 °C

4: 42 percent / EtMgBr / tetrahydrofuran / -10 °C

With aluminium trichloride; diisobutylaluminum hydride; ethylmagnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00025a033