5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-talofuranose

Base Information

• Chemical Name: 5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-talofuranose
• CAS No.: 141242-28-6
• Molecular Formula: C₂₅H₃₃BrO₅Si
• Molecular Weight: 521.524
• Mol file: 141242-28-6.mol

Synonyms:5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-talofuranose

Chemical Property of 5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-talofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-talofuranose

There total 6 articles about 5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-talofuranose 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:

(3aR,5R,6S,6aR)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2,2-dimethyltetrahydrofuro(3,2-d)(1,3)dioxol-6-ol (110920-92-8) → 5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-talofuranose (141242-28-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 94.4 percent / fused zinc chloride / 22 h / Ambient temperature

2: 74.1 percent / N-bromosuccinimide, barium carbonate / CCl₄ / 4 h / Heating

3: 65.5 percent / methanolic 1M sodium methoxide / 4 h / Ambient temperature

4: 1) phosphorus pentaoxide, 2) sodium borohydride / 1) DMF, methyl sulphoxide, 65-70 deg C, 3.5 h, 2) MeOH, 10 min at 0 deg C and 45 min at r.t.

With phosphorus pentaoxide; sodium tetrahydroborate; N-Bromosuccinimide; sodium methylate; barium carbonate; zinc(II) chloride; In tetrachloromethane;

DOI:10.1016/0008-6215(92)80042-Y

Reference yield:

3,5-O-benzylidene-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose (110920-93-9) → 5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-talofuranose (141242-28-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 74.1 percent / N-bromosuccinimide, barium carbonate / CCl₄ / 4 h / Heating

2: 65.5 percent / methanolic 1M sodium methoxide / 4 h / Ambient temperature

3: 1) phosphorus pentaoxide, 2) sodium borohydride / 1) DMF, methyl sulphoxide, 65-70 deg C, 3.5 h, 2) MeOH, 10 min at 0 deg C and 45 min at r.t.

With phosphorus pentaoxide; sodium tetrahydroborate; N-Bromosuccinimide; sodium methylate; barium carbonate; In tetrachloromethane;

DOI:10.1016/0008-6215(92)80042-Y

Reference yield:

tert-butylchlorodiphenylsilane (58479-61-1) → 5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-talofuranose (141242-28-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 99.7 percent / 4-dimethylaminopyridine / pyridine / 20 h / Ambient temperature

2: 94.4 percent / fused zinc chloride / 22 h / Ambient temperature

3: 74.1 percent / N-bromosuccinimide, barium carbonate / CCl₄ / 4 h / Heating

4: 65.5 percent / methanolic 1M sodium methoxide / 4 h / Ambient temperature

5: 1) phosphorus pentaoxide, 2) sodium borohydride / 1) DMF, methyl sulphoxide, 65-70 deg C, 3.5 h, 2) MeOH, 10 min at 0 deg C and 45 min at r.t.

With dmap; phosphorus pentaoxide; sodium tetrahydroborate; N-Bromosuccinimide; sodium methylate; barium carbonate; zinc(II) chloride; In pyridine; tetrachloromethane;

DOI:10.1016/0008-6215(92)80042-Y

upstream raw materials:

5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose

(3aR,5R,6S,6aR)-5-((R)-2-(tert-butyldiphenylsilyloxy)-1-hydroxyethyl)-2,2-dimethyltetrahydrofuro(3,2-d)(1,3)dioxol-6-ol

3,5-O-benzylidene-6-O-tert-butyldiphenylsilyl-1,2-O-isopropylidene-α-D-glucofuranose

3-O-benzoyl-5-bromo-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-β-L-idofuranose

Downstream raw materials:

5-azido-6-O-tert-butyldiphenylsilyl-5-deoxy-1,2-O-isopropylidene-α-D-allofuranose

5-Azido-6-O-benzoyl-1,3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-glucofuranose

5-azido-6-O-tert-butyldiphenylsilyl-3,5-dideoxy-3-fluoro-1,2-O-isopropylidene-α-D-glucofuranose

5-Azido-3-O-benzoyl-5-deoxy-1,2-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-allofuranose