3,5-O-(R)-benzylidene-6,7,8,9-tetradeoxy-1,2-O-isopropylidene-α-D-gluco-dec-8-yno-1,4-furanose

Base Information

Chemical Name:3,5-O-(R)-benzylidene-6,7,8,9-tetradeoxy-1,2-O-isopropylidene-α-D-gluco-dec-8-yno-1,4-furanose
CAS No.:136839-48-0
Molecular Formula:C₂₀H₂₄O₆
Molecular Weight:360.407
Hs Code.:

Synonyms:3,5-O-(R)-benzylidene-6,7,8,9-tetradeoxy-1,2-O-isopropylidene-α-D-gluco-dec-8-yno-1,4-furanose

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Chemical Property of 3,5-O-(R)-benzylidene-6,7,8,9-tetradeoxy-1,2-O-isopropylidene-α-D-gluco-dec-8-yno-1,4-furanose

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Technology Process of 3,5-O-(R)-benzylidene-6,7,8,9-tetradeoxy-1,2-O-isopropylidene-α-D-gluco-dec-8-yno-1,4-furanose

There total 6 articles about 3,5-O-(R)-benzylidene-6,7,8,9-tetradeoxy-1,2-O-isopropylidene-α-D-gluco-dec-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: 77.0%

: 50-00-0,30525-89-4,61233-19-0
formaldehyd

: 136839-47-9
3,5-O-(R)-benzylidene-6,7,8,9-tetradeoxy-1,2-O-isopropylidene-α-D-gluco-non-8-yno-1,4-furanose

: 136839-48-0
3,5-O-(R)-benzylidene-6,7,8,9-tetradeoxy-1,2-O-isopropylidene-α-D-gluco-dec-8-yno-1,4-furanose

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.166667h;
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

: 136839-48-0
3,5-O-(R)-benzylidene-6,7,8,9-tetradeoxy-1,2-O-isopropylidene-α-D-gluco-dec-8-yno-1,4-furanose

Guidance literature:: Multi-step reaction with 6 steps

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

2: 99 percent / di(isobutylaluminum hydride / CH₂Cl₂ / 0.92 h / -40 °C

3: 98 percent / NaBH₄ / methanol / 0.33 h / 21 °C

4: 48 percent / pyridine / 6 h / 0 °C

5: 96 percent / dimethylsulfoxide / 0.5 h / 10 °C

6: 77 percent / n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C

With pyridine; sodium tetrahydroborate; n-butyllithium; diisobutylaluminium hydride; In tetrahydrofuran; methanol; hexane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo00025a033

Reference yield:

: 136839-41-3
3,5-O-(R)-benzylidene-6-deoxy-1,2-O-isopropylidene-α-D-gluco-hepto-1,4-furanose

: 136839-48-0
3,5-O-(R)-benzylidene-6,7,8,9-tetradeoxy-1,2-O-isopropylidene-α-D-gluco-dec-8-yno-1,4-furanose

Guidance literature:: Multi-step reaction with 3 steps

1: 48 percent / pyridine / 6 h / 0 °C

2: 96 percent / dimethylsulfoxide / 0.5 h / 10 °C

3: 77 percent / n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C

With pyridine; n-butyllithium; In tetrahydrofuran; hexane; dimethyl sulfoxide;
DOI:10.1021/jo00025a033