1,3,4,5-tetra-O-benzyl-8-bromo-7,8-dideoxy-D-glycero-L-galacto-oct-7-ynitol

Base Information

• Chemical Name: 1,3,4,5-tetra-O-benzyl-8-bromo-7,8-dideoxy-D-glycero-L-galacto-oct-7-ynitol
• CAS No.: 875140-32-2
• Molecular Formula: C₃₆H₃₇BrO₆
• Molecular Weight: 645.59
• Mol file: 875140-32-2.mol

Synonyms:1,3,4,5-tetra-O-benzyl-8-bromo-7,8-dideoxy-D-glycero-L-galacto-oct-7-ynitol

Chemical Property of 1,3,4,5-tetra-O-benzyl-8-bromo-7,8-dideoxy-D-glycero-L-galacto-oct-7-ynitol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,3,4,5-tetra-O-benzyl-8-bromo-7,8-dideoxy-D-glycero-L-galacto-oct-7-ynitol

There total 2 articles about 1,3,4,5-tetra-O-benzyl-8-bromo-7,8-dideoxy-D-glycero-L-galacto-oct-7-ynitol 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: 76.0%

1,3,4,5-tetra-O-benzyl-7,8-dideoxy-8-C-(trimethylsilyl)-D-glycero-L-galacto-oct-7-ynitol (875140-30-0) → 1,3,4,5-tetra-O-benzyl-8-bromo-7,8-dideoxy-D-glycero-L-galacto-oct-7-ynitol (875140-32-2)

Guidance literature:

With N-Bromosuccinimide; silver nitrate; In acetone; for 8h;

DOI:10.1002/hlca.200590235

Reference yield:

2,3,4,6-tetra-O-benzyl-D-galactopyranose (6386-24-9) → 1,3,4,5-tetra-O-benzyl-8-bromo-7,8-dideoxy-D-glycero-L-galacto-oct-7-ynitol (875140-32-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: BuLi / hexane; tetrahydrofuran / 0.5 h / -78 °C

1.2: 39 percent / hexane; tetrahydrofuran / 24 h / 23 °C

2.1: 76 percent / N-bromosuccinimide; AgNO₃ / acetone / 8 h

With N-Bromosuccinimide; n-butyllithium; silver nitrate; In tetrahydrofuran; hexane; acetone;

DOI:10.1002/hlca.200590235

Reference yield:

1,3,4,5-tetra-O-benzyl-8-bromo-7,8-dideoxy-D-glycero-L-galacto-oct-7-ynitol (875140-32-2) → (3S,4S,5R,6S,7R)-4,5,6-Tris-benzyloxy-7-benzyloxymethyl-2-[1-bromo-meth-(Z)-ylidene]-oxepan-3-ol

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 23 ℃; for 1.5h;

DOI:10.1002/hlca.200590235

upstream raw materials:

1,3,4,5-tetra-O-benzyl-7,8-dideoxy-8-C-(trimethylsilyl)-D-glycero-L-galacto-oct-7-ynitol

2,3,4,6-tetra-O-benzyl-D-galactopyranose