Methyl 4-deoxy-2,3,6-tri-O-benzyl-4-C-(2-bromo-1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside

Base Information

Chemical Name:Methyl 4-deoxy-2,3,6-tri-O-benzyl-4-C-(2-bromo-1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside
CAS No.:138459-06-0
Molecular Formula:C₃₇H₄₅BrO₉
Molecular Weight:713.663
Hs Code.:

Synonyms:Methyl 4-deoxy-2,3,6-tri-O-benzyl-4-C-(2-bromo-1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside

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Chemical Property of Methyl 4-deoxy-2,3,6-tri-O-benzyl-4-C-(2-bromo-1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside

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Technology Process of Methyl 4-deoxy-2,3,6-tri-O-benzyl-4-C-(2-bromo-1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside

There total 11 articles about Methyl 4-deoxy-2,3,6-tri-O-benzyl-4-C-(2-bromo-1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside 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: 91.0%

: 138459-05-9
Methyl 4-deoxy-2,3,6-tri-O-benzyl-4-C-(2-bromo-6-O-(tert-butyldiphenylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside

: 138459-06-0
Methyl 4-deoxy-2,3,6-tri-O-benzyl-4-C-(2-bromo-1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 25 ℃; for 3h;
DOI:10.1021/jo00029a024

Reference yield:

: 10323-20-3
D-Arabinose

: 138459-06-0
Methyl 4-deoxy-2,3,6-tri-O-benzyl-4-C-(2-bromo-1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside

Guidance literature:: Multi-step reaction with 8 steps

1: 1) conc. HCl / 1) 30 min, 2) 2 h

2: 86 percent / p-TsOH / methanol; H₂O / 36 h / -10 °C

3: 89 percent / imidazole / dimethylformamide / 18 h / 25 °C

4: 97 percent / NBS, 2,6-lutidine / acetonitrile; H₂O / 0.17 h / 25 °C

6: 81 percent / imidazole / dimethylformamide / 8 h

7: 32 percent / NBS, Br₂ / acetonitrile / 0.25 h / 25 °C

8: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; N-Bromosuccinimide; tetrabutyl ammonium fluoride; bromine; toluene-4-sulfonic acid; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00029a024

Reference yield:

: 138458-95-4
4,5-Di-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-arabinose diethyl dithioacetal

: 138459-06-0
Methyl 4-deoxy-2,3,6-tri-O-benzyl-4-C-(2-bromo-1,2-dideoxy-3,4-O-isopropylidene-β-D-gluco-hexopyranos-1-yl)-α-D-gluco-hexopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 97 percent / NBS, 2,6-lutidine / acetonitrile; H₂O / 0.17 h / 25 °C

3: 81 percent / imidazole / dimethylformamide / 8 h

4: 32 percent / NBS, Br₂ / acetonitrile / 0.25 h / 25 °C

5: 91 percent / tetrabutylammonium fluoride / tetrahydrofuran / 3 h / 25 °C

With 1H-imidazole; 2,6-dimethylpyridine; N-Bromosuccinimide; tetrabutyl ammonium fluoride; bromine; In tetrahydrofuran; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00029a024