pent-4'-enyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

Base Information

• Chemical Name: pent-4'-enyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside
• CAS No.: 131684-73-6
• Molecular Formula: C₅₉H₆₄O₁₁
• Molecular Weight: 949.151
• Mol file: 131684-73-6.mol

Synonyms:pent-4'-enyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

Chemical Property of pent-4'-enyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of pent-4'-enyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside

There total 4 articles about pent-4'-enyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside 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: 80.0%

phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside (38184-10-0) + pent-4'-enyl 2-O-benzyl-4,6-benzylidene-α-D-glucopyranoside (131684-79-2) → pent-4'-enyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside + pent-4'-enyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (131684-73-6)

Guidance literature:

With 4 A molecular sieve; methyl trifluoromethanesulfonate; In diethyl ether; at 20 ℃; for 17.5h;

DOI:10.1016/S0008-6215(03)00255-6

Reference yield:

D-Glucose (2280-44-6) → pent-4'-enyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (131684-73-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 63 percent / CSA / 48 h / 140 °C

2: 46 percent / CSA / dimethylformamide / 7 h / 65 °C / 195.02 - 210.02 Torr

3: NaOH; Bu₄NHSO₄ / CH₂Cl₂; H₂O / 46 h / 41 °C

4: 80 percent / 4 Angstroem molecular sieves; MeOTf / diethyl ether / 17.5 h / 20 °C

With sodium hydroxide; 4 A molecular sieve; camphor-10-sulfonic acid; tetra(n-butyl)ammonium hydrogensulfate; methyl trifluoromethanesulfonate; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(03)00255-6

Reference yield:

n-Pent-4-enyl alcohol (821-09-0) → pent-4'-enyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside (131684-73-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 63 percent / CSA / 48 h / 140 °C

2: 46 percent / CSA / dimethylformamide / 7 h / 65 °C / 195.02 - 210.02 Torr

3: NaOH; Bu₄NHSO₄ / CH₂Cl₂; H₂O / 46 h / 41 °C

4: 80 percent / 4 Angstroem molecular sieves; MeOTf / diethyl ether / 17.5 h / 20 °C

With sodium hydroxide; 4 A molecular sieve; camphor-10-sulfonic acid; tetra(n-butyl)ammonium hydrogensulfate; methyl trifluoromethanesulfonate; In diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(03)00255-6

upstream raw materials:

phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside

pent-4'-enyl 2-O-benzyl-4,6-benzylidene-α-D-glucopyranoside

D-Glucose

n-Pent-4-enyl alcohol

Downstream raw materials:

5'-hydroxypentyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->3)-2-O-benzyl-4,6-O-benzylidene-α-D-glucopyranoside