3,7-anhydro-4,5,6-tri-O-benzyl-8-bromo-1,2,8-trideoxy-D-glycero-D-gulo-oct-1-enitol

Base Information

• Chemical Name: 3,7-anhydro-4,5,6-tri-O-benzyl-8-bromo-1,2,8-trideoxy-D-glycero-D-gulo-oct-1-enitol
• CAS No.: 854654-14-1
• Molecular Formula: C₂₉H₃₁BrO₄
• Molecular Weight: 523.467
• Mol file: 854654-14-1.mol

Synonyms:3,7-anhydro-4,5,6-tri-O-benzyl-8-bromo-1,2,8-trideoxy-D-glycero-D-gulo-oct-1-enitol

Chemical Property of 3,7-anhydro-4,5,6-tri-O-benzyl-8-bromo-1,2,8-trideoxy-D-glycero-D-gulo-oct-1-enitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,7-anhydro-4,5,6-tri-O-benzyl-8-bromo-1,2,8-trideoxy-D-glycero-D-gulo-oct-1-enitol

There total 5 articles about 3,7-anhydro-4,5,6-tri-O-benzyl-8-bromo-1,2,8-trideoxy-D-glycero-D-gulo-oct-1-enitol 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: 61.0%

benzyl bromide (100-39-0) + 3,7-anhydro-1,2-dideoxy-8-O-(4-toluenesulfonyl)-D-glycero-D-gulo-oct-1-enitol (202803-14-3) → 3,7-anhydro-4,5,6-tri-O-benzyl-8-bromo-1,2,8-trideoxy-D-glycero-D-gulo-oct-1-enitol (854654-14-1)

Guidance literature:

benzyl bromide; 3,7-anhydro-1,2-dideoxy-8-O-(4-toluenesulfonyl)-D-glycero-D-gulo-oct-1-enitol; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 2h;

With sodium bromide; In N,N-dimethyl-formamide; at 80 ℃;

DOI:10.1002/ejoc.200600455

Reference yield: 36.0%

3,7-anhydro-1,2-dideoxy-8-O-(4-toluenesulfonyl)-D-glycero-D-gulo-oct-1-enitol + benzyl bromide (100-39-0) → 3,7-anhydro-4,5,6-tri-O-benzyl-8-bromo-1,2,8-trideoxy-D-glycero-D-gulo-oct-1-enitol (854654-14-1)

Guidance literature:

3,7-anhydro-1,2-dideoxy-8-O-(4-toluenesulfonyl)-D-glycero-D-gulo-oct-1-enitol; benzyl bromide; With sodium hydride; In N,N-dimethyl-formamide; for 3h;

With sodium bromide; In N,N-dimethyl-formamide; at 80 ℃;

DOI:10.1016/j.tetasy.2005.02.027

Reference yield:

3,7-anhydro-1,2-dideoxy-D-glycero-D-gulo-oct-1-enitol (51450-27-2) → 3,7-anhydro-4,5,6-tri-O-benzyl-8-bromo-1,2,8-trideoxy-D-glycero-D-gulo-oct-1-enitol (854654-14-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 49 percent / pyridine / 48 h / 20 °C

2.1: sodium hydride / dimethylformamide / 2 h / 20 °C

2.2: 61 percent / sodium bromide / dimethylformamide / 80 °C

With pyridine; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200600455

upstream raw materials:

benzyl bromide

3,7-anhydro-1,2-dideoxy-8-O-(4-toluenesulfonyl)-D-glycero-D-gulo-oct-1-enitol

3,7-anhydro-1,2-dideoxy-D-glycero-D-gulo-oct-1-enitol

4,5,6,8-Tetra-O-acetyl-3,7-anhydro-1,2-didesoxy-β-D-gluco-oct-1-enitol

Downstream raw materials:

3,7-anhydro-4,5,6-tri-O-benzyl-1,2,8-trideoxy-D-gulo-oct-1,7-dienitol