phenyl 2-O-acetyl-6-O-allyldimethylsilyl-3,4-bis-O-tert-butyldimethylsilyl-1-seleno-β-D-glucopyranoside

Base Information

• Chemical Name: phenyl 2-O-acetyl-6-O-allyldimethylsilyl-3,4-bis-O-tert-butyldimethylsilyl-1-seleno-β-D-glucopyranoside
• CAS No.: 866417-27-8
• Molecular Formula: C₃₁H₅₆O₆SeSi₃
• Molecular Weight: 687.999
• Mol file: 866417-27-8.mol

Synonyms:phenyl 2-O-acetyl-6-O-allyldimethylsilyl-3,4-bis-O-tert-butyldimethylsilyl-1-seleno-β-D-glucopyranoside

Chemical Property of phenyl 2-O-acetyl-6-O-allyldimethylsilyl-3,4-bis-O-tert-butyldimethylsilyl-1-seleno-β-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2-O-acetyl-6-O-allyldimethylsilyl-3,4-bis-O-tert-butyldimethylsilyl-1-seleno-β-D-glucopyranoside

There total 2 articles about phenyl 2-O-acetyl-6-O-allyldimethylsilyl-3,4-bis-O-tert-butyldimethylsilyl-1-seleno-β-D-glucopyranoside 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: 90.0%

phenyl 2-O-acetyl-3,4-bis-O-tert-butyldimethylsilyl-1-seleno-β-D-glucopyranoside (866417-31-4) + Allylchlorodimethylsilane (4028-23-3) → phenyl 2-O-acetyl-6-O-allyldimethylsilyl-3,4-bis-O-tert-butyldimethylsilyl-1-seleno-β-D-glucopyranoside (866417-27-8)

Guidance literature:

With dmap; triethylamine; In toluene; at 20 ℃;

DOI:10.1016/j.tetlet.2005.07.087

Reference yield:

phenyl 3,4-bis-O-tert-butyldimethylsilyl-6-O-trityl-1-seleno-β-D-glucose (288584-99-6) → phenyl 2-O-acetyl-6-O-allyldimethylsilyl-3,4-bis-O-tert-butyldimethylsilyl-1-seleno-β-D-glucopyranoside (866417-27-8)

Guidance literature:

Multi-step reaction with 3 steps

1: DMAP / acetonitrile / 12 h / 20 °C

2: 1.0 g / aq. TFA / CHCl₃ / 1 h / 20 °C

3: 90 percent / Et₃N; DMAP / toluene / 0.5 h / 20 °C

With dmap; triethylamine; trifluoroacetic acid; In chloroform; toluene; acetonitrile;

DOI:10.1021/jm051039n

Reference yield:

phenyl 2-O-acetyl-6-O-allyldimethylsilyl-3,4-bis-O-tert-butyldimethylsilyl-1-seleno-β-D-glucopyranoside (866417-27-8) → 5-O-acetyl-4,8-anhydro-9-O-benzoyl-2,3-dideoxy-D-glycero-D-gulo-nonitol (882528-65-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 72 percent / AIBN; Bu₃SnH / benzene / 4 h / Heating

2: 61 percent / KBr; HBr; AcOOH / AcOH / dimethylformamide / 12 h / 20 °C

3: 64 percent / imidazole / dimethylformamide / 0.75 h / -40 °C

4: 99 percent / pyridine / 0.5 h / 20 °C

5: 99 percent / TBAF; AcOH / tetrahydrofuran / 48 h / 20 °C

With pyridine; 1H-imidazole; peracetic acid; 2,2'-azobis(isobutyronitrile); tetrabutyl ammonium fluoride; hydrogen bromide; tri-n-butyl-tin hydride; acetic acid; potassium bromide; acetic acid; In tetrahydrofuran; N,N-dimethyl-formamide; benzene;

DOI:10.1021/jm051039n

upstream raw materials:

phenyl 2-O-acetyl-3,4-bis-O-tert-butyldimethylsilyl-1-seleno-β-D-glucopyranoside

Allylchlorodimethylsilane

phenyl 3,4-bis-O-tert-butyldimethylsilyl-6-O-trityl-1-seleno-β-D-glucose

Downstream raw materials:

5-O-acetyl-4,8-anhydro-9-O-benzoyl-2,3-dideoxy-D-glycero-D-gulo-nonitol

5-O-acetyl-4,8-anhydro-6,7-bis-O-tert-butyldimethylsilyl-1-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-glycero-D-gulo-nonitol

5-O-acetyl-4,8-anhydro-9-O-benzoyl-6,7-bis-O-tert-butyldimethylsilyl-1-O-tert-butyldiphenylsilyl-2,3-dideoxy-D-glycero-D-gulo-nonitol

5-O-acetyl-4,8-anhydro-9-O-benzoyl-2,3-dideoxy-D-glycero-D-gulo-nonitol 1,6,7-trisphosphate