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

Base Information

• Chemical Name: (3R,4S,5S,6S)-1,3,4,5-tetra-O-benzyl-2-methylene-oct-7-ene-1,3,4,5,6-pentaol
• CAS No.: 1045730-57-1
• Molecular Formula: C₃₇H₄₀O₅
• Molecular Weight: 564.722
• Mol file: 1045730-57-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about (3R,4S,5S,6S)-1,3,4,5-tetra-O-benzyl-2-methylene-oct-7-ene-1,3,4,5,6-pentaol 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: 75.0%

(3R,4S,5R,6S)-1,3,4,5-tetra-O-benzyl-6-O-(3,4-dimethoxybenzyl)-2-methylene-oct-7-ene-1,3,4,5,6-pentol (1045730-63-9) → (3R,4S,5S,6S)-1,3,4,5-tetra-O-benzyl-2-methylene-oct-7-ene-1,3,4,5,6-pentaol (1045730-57-1)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 ℃; for 1.33333h;

DOI:10.1016/j.carres.2008.04.010

Reference yield:

C35H36O5 (1045730-81-1) + (3R,4R,5S)-1,3,4,5-tetra-O-benzyl-2-methylene-hexane-1,3,4,5,6-pentaol (1045730-56-0) + vinyl magnesium bromide (1826-67-1) → (3R,4S,5S,6R)-1,3,4,5-tetra-O-benzyl-2-methylene-oct-7-ene-1,3,4,5,6-pentaol (1045730-55-9) + (3R,4S,5S,6S)-1,3,4,5-tetra-O-benzyl-2-methylene-oct-7-ene-1,3,4,5,6-pentaol (1045730-57-1)

Guidance literature:

(3R,4R,5S)-1,3,4,5-tetra-O-benzyl-2-methylene-hexane-1,3,4,5,6-pentaol; With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;

C₃₅H₃₆O₅; vinyl magnesium bromide; In tetrahydrofuran; dichloromethane; at 0 - 20 ℃; for 1h; Overall yield = 64 %; Overall yield = 5.78 g; Optical yield = 42.857 %de;

DOI:10.1016/j.tet.2013.09.098

Reference yield:

C35H36O5 (1045730-81-1) + vinyl magnesium bromide (1826-67-1) → (3R,4S,5S,6R)-1,3,4,5-tetra-O-benzyl-2-methylene-oct-7-ene-1,3,4,5,6-pentaol (1045730-55-9) + (3R,4S,5S,6S)-1,3,4,5-tetra-O-benzyl-2-methylene-oct-7-ene-1,3,4,5,6-pentaol (1045730-57-1)

Guidance literature:

In tetrahydrofuran; at 0 ℃; for 1.5h;

DOI:10.1016/j.carres.2008.04.010

upstream raw materials:

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

C₃₅H₃₆O₅

vinyl magnesium bromide

(3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)-6-(tert-butyldiphenylsilyloxy)hexan-2-ol

Downstream raw materials:

(1S,2S,3S,4R)-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-1,2,3,4-tetrol