Pent-4-enyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside

Base Information

• Chemical Name: Pent-4-enyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside
• CAS No.: 344550-94-3
• Molecular Formula: C₃₂H₃₆O₆
• Molecular Weight: 516.634
• Mol file: 344550-94-3.mol

Synonyms:Pent-4-enyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside

Chemical Property of Pent-4-enyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Pent-4-enyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside

There total 5 articles about Pent-4-enyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside 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: 90.0%

benzyl bromide (100-39-0) + 4,6-O-benzylidene-(pent-4-enyl)-β-D-galactopyranoside (143416-42-6) → Pent-4-enyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside (344550-94-3)

Guidance literature:

4,6-O-benzylidene-(pent-4-enyl)-β-D-galactopyranoside; With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 0.5h;

benzyl bromide; With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; at 20 ℃; Further stages.;

DOI:10.1039/b006981g

Reference yield:

n-Pent-4-enyl alcohol (821-09-0) → Pent-4-enyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside (344550-94-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: BF₃*Et₂O / CH₂Cl₂ / 10 h / 20 °C

2.1: 12.5 g / NaOMe; MeOH / 2 h

3.1: 99 percent / CSA / CHCl₃ / 1.5 h / Heating

4.1: NaH / dimethylformamide / 0.5 h / 20 °C

4.2: 90 percent / Bu₄NI / dimethylformamide / 20 °C

With methanol; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; In dichloromethane; chloroform; N,N-dimethyl-formamide;

DOI:10.1039/b006981g

Reference yield:

(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran-3,4,5-triol (132871-96-6) → Pent-4-enyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside (344550-94-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 99 percent / CSA / CHCl₃ / 1.5 h / Heating

2.1: NaH / dimethylformamide / 0.5 h / 20 °C

2.2: 90 percent / Bu₄NI / dimethylformamide / 20 °C

With camphor-10-sulfonic acid; sodium hydride; In chloroform; N,N-dimethyl-formamide;

DOI:10.1039/b006981g

upstream raw materials:

benzyl bromide

4,6-O-benzylidene-(pent-4-enyl)-β-D-galactopyranoside

n-Pent-4-enyl alcohol

(2R,3R,4S,5R,6R)-2-(hydroxymethyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran-3,4,5-triol

Downstream raw materials:

Benzyl O-[2,3-di-O-benzyl-4-O-chloroacetyl-6-O-(4-methoxyphenyl)-α-D-galactopyranosyl]-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-β-D-galactopyranoside

Benzyl O-[2,3-di-O-benzyl-4-O-chloroacetyl-6-O-(4-methoxyphenyl)-α-D-galactopyranosyl]-(1->4)-6-O-acetyl-2,3-di-O-benzyl-β-D-galactopyranoside

Benzyl O-[2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-α-D-galactopyranosyl]-(1->4)-2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-β-D-galactopyranoside

Benzyl O-(6-O-acetyl-2,3-di-O-benzyl-4-O-chloroacetyl-α-D-galactopyranosyl)-(1->4)-O-2,3-di-O-benzyl-6-O-(4-methoxyphenyl)-β-D-galactopyranoside