2-Bromo-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-C-<(tert-butyldiphenylsiloxy)methyl>-β-D-gluco-hexapyranose

Base Information

Chemical Name:2-Bromo-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-C-<(tert-butyldiphenylsiloxy)methyl>-β-D-gluco-hexapyranose
CAS No.:138458-99-8
Molecular Formula:C₄₂H₅₃BrO₅Si₂
Molecular Weight:773.955
Hs Code.:

Synonyms:2-Bromo-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-C-<(tert-butyldiphenylsiloxy)methyl>-β-D-gluco-hexapyranose

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Chemical Property of 2-Bromo-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-C-<(tert-butyldiphenylsiloxy)methyl>-β-D-gluco-hexapyranose

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Technology Process of 2-Bromo-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-C-<(tert-butyldiphenylsiloxy)methyl>-β-D-gluco-hexapyranose

There total 8 articles about 2-Bromo-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-C-<(tert-butyldiphenylsiloxy)methyl>-β-D-gluco-hexapyranose 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: 52.0%

: 138458-98-7
(E)-6-O-(tert-Butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-<(tert-butyldiphenylsiloxy)methyl>-D-gluco-hex-1-enose

: 138458-99-8
2-Bromo-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-C-<(tert-butyldiphenylsiloxy)methyl>-β-D-gluco-hexapyranose

Guidance literature:: With N-Bromosuccinimide; bromine; In acetonitrile; for 0.0833333h;
DOI:10.1021/jo00029a024

Reference yield:

: 10323-20-3
D-Arabinose

: 138458-99-8
2-Bromo-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-C-<(tert-butyldiphenylsiloxy)methyl>-β-D-gluco-hexapyranose

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: 1) imidazole, 2) pyridine / 1) DMF, 25 deg C, 4 h, 2) 60 deg C, 2 d

4: 95 percent / NBS, 2,6-lutidine / acetonitrile; H₂O / 0.17 h / 25 °C

5: 12 percent / tetrahydrofuran / 12 h / 25 °C

6: 99 percent / DIBAL-H / tetrahydrofuran; toluene / 0.42 h / -78 °C

7: 100 percent / imidazole / dimethylformamide / 2 h / 25 °C

8: 52 percent / Br₂, NBS / acetonitrile / 0.08 h

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

Reference yield:

: 138459-10-6
(E)-6-O-(tert-Butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-(hydroxymethyl)-D-gluco-hex-1-enose

: 138458-99-8
2-Bromo-6-O-(tert-butyldiphenylsilyl)-3,4-O-isopropylidene-1,2-dideoxy-1-C-<(tert-butyldiphenylsiloxy)methyl>-β-D-gluco-hexapyranose

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / imidazole / dimethylformamide / 2 h / 25 °C

2: 52 percent / Br₂, NBS / acetonitrile / 0.08 h

With 1H-imidazole; N-Bromosuccinimide; bromine; In N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo00029a024