1-((2R,3R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-1-vinyl-pent-4-enyloxymethyl)-4-methoxy-benzene

Base Information

• Chemical Name: 1-((2R,3R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-1-vinyl-pent-4-enyloxymethyl)-4-methoxy-benzene
• CAS No.: 312757-17-8
• Molecular Formula: C₃₇H₄₀O₅
• Molecular Weight: 564.722
• Mol file: 312757-17-8.mol

Synonyms:1-((2R,3R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-1-vinyl-pent-4-enyloxymethyl)-4-methoxy-benzene

Chemical Property of 1-((2R,3R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-1-vinyl-pent-4-enyloxymethyl)-4-methoxy-benzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-((2R,3R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-1-vinyl-pent-4-enyloxymethyl)-4-methoxy-benzene

There total 4 articles about 1-((2R,3R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-1-vinyl-pent-4-enyloxymethyl)-4-methoxy-benzene 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: 89.0%

Methyltriphenylphosphonium bromide (1779-49-3) + (3S,4R)-1,3,4-Tris-benzyloxy-5-(4-methoxy-benzyloxy)-hept-6-en-2-one (312757-15-6) → 1-((2R,3R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-1-vinyl-pent-4-enyloxymethyl)-4-methoxy-benzene (312757-17-8)

Guidance literature:

With n-butyllithium;

DOI:10.1016/S0040-4039(00)01355-1

Reference yield:

2,3,5-tri-O-benzyl-D-arabinofuranose (160549-10-0) → 1-((2R,3R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-1-vinyl-pent-4-enyloxymethyl)-4-methoxy-benzene (312757-17-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / tetrahydrofuran

2: 83 percent / NaH / dimethylformamide / 0 °C

3: 77 percent / (COCl)2; DMSO; Et₃N

4: 89 percent / n-BuLi

With n-butyllithium; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; 1: Grignard reaction / 2: Alkylation / 3: Oxidation / 4: Wittig olefination;

DOI:10.1016/S0040-4039(00)01355-1

Reference yield:

(2R,3R,4R)-1,3,4-Tris-benzyloxy-hept-6-ene-2,5-diol (312757-11-2) → 1-((2R,3R)-2,3-Bis-benzyloxy-4-benzyloxymethyl-1-vinyl-pent-4-enyloxymethyl)-4-methoxy-benzene (312757-17-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / NaH / dimethylformamide / 0 °C

2: 77 percent / (COCl)2; DMSO; Et₃N

3: 89 percent / n-BuLi

With n-butyllithium; oxalyl dichloride; sodium hydride; dimethyl sulfoxide; triethylamine; In N,N-dimethyl-formamide; 1: Alkylation / 2: Oxidation / 3: Wittig olefination;

DOI:10.1016/S0040-4039(00)01355-1

upstream raw materials:

Methyltriphenylphosphonium bromide

(3S,4R)-1,3,4-Tris-benzyloxy-5-(4-methoxy-benzyloxy)-hept-6-en-2-one

2,3,5-tri-O-benzyl-D-arabinofuranose

(2R,3R,4R)-1,3,4-Tris-benzyloxy-hept-6-ene-2,5-diol

Downstream raw materials:

1-((1S,4R,5R)-4,5-Bis-benzyloxy-3-benzyloxymethyl-cyclopent-2-enyloxymethyl)-4-methoxy-benzene