(2R,3R,4R,5S,6S)-1,3,4,5-tetra-O-benzyl-oct-7-ene-1,2,3,4,5,6-hexaol

Base Information

• Chemical Name: (2R,3R,4R,5S,6S)-1,3,4,5-tetra-O-benzyl-oct-7-ene-1,2,3,4,5,6-hexaol
• CAS No.: 866336-41-6
• Molecular Formula: C₃₆H₄₀O₆
• Molecular Weight: 568.71
• Mol file: 866336-41-6.mol

Synonyms:(2R,3R,4R,5S,6S)-1,3,4,5-tetra-O-benzyl-oct-7-ene-1,2,3,4,5,6-hexaol

Chemical Property of (2R,3R,4R,5S,6S)-1,3,4,5-tetra-O-benzyl-oct-7-ene-1,2,3,4,5,6-hexaol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5S,6S)-1,3,4,5-tetra-O-benzyl-oct-7-ene-1,2,3,4,5,6-hexaol

There total 3 articles about (2R,3R,4R,5S,6S)-1,3,4,5-tetra-O-benzyl-oct-7-ene-1,2,3,4,5,6-hexaol 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: 65.0%

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) + vinyl magnesium bromide (1826-67-1) → (2R,3R,4R,5S,6R)-1,3,4,5-tetra-O-benzyl-oct-7-ene-1,2,3,4,5,6-hexaol (866336-42-7) + (2R,3R,4R,5S,6S)-1,3,4,5-tetra-O-benzyl-oct-7-ene-1,2,3,4,5,6-hexaol (866336-41-6)

Guidance literature:

In tetrahydrofuran; at 0 - 20 ℃;

DOI:10.1039/b718060h

Reference yield: 48.0%

2,3,4,6-tetra-O-benzyl-D-galactopyranose (6386-24-9) + vinyl magnesium bromide (1826-67-1) → (2R,3R,4R,5S,6S)-1,3,4,5-tetra-O-benzyl-oct-7-ene-1,2,3,4,5,6-hexaol (866336-41-6) + (2R,3S,4R,5S,6R)-1,3,4,5-tetra-O-benzyl-oct-7-ene-1,2,3,4,5,6-hexaol (1020653-97-7)

Guidance literature:

vinyl magnesium bromide; With dimethyl zinc(II); In tetrahydrofuran; at 0 ℃; Inert atmosphere;

2,3,4,6-tetra-O-benzyl-D-galactopyranose; In tetrahydrofuran; at 0 - 20 ℃; for 21h; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; optical yield given as %de; Inert atmosphere;

DOI:10.1016/j.tet.2009.01.014

Reference yield:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose (4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9) + vinyl magnesium bromide (1826-67-1) + diethylzinc (557-20-0) → (2R,3R,4R,5S,6R)-1,3,4,5-tetra-O-benzyl-oct-7-ene-1,2,3,4,5,6-hexaol (866336-42-7) + (2R,3R,4R,5S,6S)-1,3,4,5-tetra-O-benzyl-oct-7-ene-1,2,3,4,5,6-hexaol (866336-41-6) + C36H42O6

Guidance literature:

vinyl magnesium bromide; diethylzinc; In tetrahydrofuran; at 0 ℃; Inert atmosphere;

2,3,4,6-Tetra-O-benzyl-D-glucopyranose; In tetrahydrofuran; at 0 - 20 ℃; for 21h; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; Inert atmosphere;

DOI:10.1016/j.tet.2009.01.014

upstream raw materials:

2,3,4,6-Tetra-O-benzyl-D-glucopyranose

vinyl magnesium bromide

diethylzinc

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

Downstream raw materials:

(2,3,6-tri-O-benzyl-α-D-glucofuranosyl)ethene

(2,3,5,6-tetra-O-benzyl-α-D-glucofuranosyl)ethene

C₄₀H₄₄O₈

C₅₀H₅₀Br₂O₆