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

Base Information

• Chemical Name: 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
• CAS No.: 138459-05-9
• Molecular Formula: C₅₃H₆₃BrO₉Si
• Molecular Weight: 952.067
• Mol file: 138459-05-9.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 10 articles about 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 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: 32.0%

(E)-6-O-(tert-Butyldiphenylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexo-pyranosid-4-yl)-D-gluco-hex-1-enose (138459-04-8,138514-63-3) → 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 (138459-05-9)

Guidance literature:

With N-Bromosuccinimide; bromine; In acetonitrile; at 25 ℃; for 0.25h;

DOI:10.1021/jo00029a024

Reference yield:

D-Arabinose (10323-20-3) → 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 (138459-05-9)

Guidance literature:

Multi-step reaction with 7 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

With 1H-imidazole; 2,6-dimethylpyridine; hydrogenchloride; N-Bromosuccinimide; bromine; toluene-4-sulfonic acid; In methanol; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00029a024

Reference yield:

4,5-Di-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-arabinose diethyl dithioacetal (138458-95-4) → 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 (138459-05-9)

Guidance literature:

Multi-step reaction with 4 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

With 1H-imidazole; 2,6-dimethylpyridine; N-Bromosuccinimide; bromine; In water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jo00029a024

upstream raw materials:

(E)-6-O-(tert-Butyldiphenylsilyl)-1,2-dideoxy-3,4-O-isopropylidene-1-(methyl 2,3,6-tri-O-benzyl-α-D-gluco-hexo-pyranosid-4-yl)-D-gluco-hex-1-enose

D-Arabinose

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

4,5-Di-O-(tert-butyldimethylsilyl)-2,3-O-isopropylidene-D-arabinose

Downstream raw materials:

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