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

Base Information

Chemical Name: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
CAS No.:136839-35-5
Molecular Formula:C₂₆H₂₅NO₉
Molecular Weight:495.486
Hs Code.:

Synonyms: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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Chemical Property of 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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Technology Process of 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

There total 5 articles about 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 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: 65.0%

: 122-04-3
4-nitro-benzoyl chloride

: 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

: 136839-35-5
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

Guidance literature:: With pyridine; at 21 ℃; for 1.5h;
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

: 136839-35-5
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

Guidance literature:: Multi-step reaction with 5 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

5: 65 percent / pyridine / 1.5 h / 21 °C

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

Reference yield:

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

: 136839-35-5
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

Guidance literature:: Multi-step reaction with 4 steps

1: 77.4 percent / AlCl₃ / diethyl ether; CH₂Cl₂ / 0.5 h / 21 °C

2: 99 percent / di(isobutyl)aluminum hydride / CH₂Cl₂ / -40 °C

3: 42 percent / EtMgBr / tetrahydrofuran / -10 °C

4: 65 percent / pyridine / 1.5 h / 21 °C

With pyridine; aluminium trichloride; diisobutylaluminum hydride; ethylmagnesium bromide; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo00025a033