allyl 3-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside

Base Information

• Chemical Name: allyl 3-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside
• CAS No.: 400090-99-5
• Molecular Formula: C₂₃H₂₆O₆
• Molecular Weight: 398.456
• Mol file: 400090-99-5.mol

Synonyms:allyl 3-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside

Chemical Property of allyl 3-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of allyl 3-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside

There total 4 articles about allyl 3-O-benzyl-4,6-O-(S)-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: 91.0%

benzyl bromide (100-39-0) + allyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside (119237-96-6) → allyl 3-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside (400090-99-5)

Guidance literature:

allyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside; With di(n-butyl)tin oxide; In toluene; for 16h; Heating;

benzyl bromide; In toluene; at 90 ℃; for 8h;

DOI:10.1002/1099-0690(200110)2001:20<3849::AID-EJOC3849>3.0.CO;2-Q

Reference yield:

allyl β-D-galactopyranoside (2595-07-5,821794-45-0) → allyl 3-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside (400090-99-5)

Guidance literature:

Multi-step reaction with 2 steps

1: camphor-10-sulfonic acid / acetonitrile / 20 °C

2: 18-crown-6 ether; potassium hydroxide / tetrahydrofuran / 0.33 h

With 18-crown-6 ether; camphor-10-sulfonic acid; potassium hydroxide; In tetrahydrofuran; acetonitrile;

DOI:10.1002/ejoc.201101539

Reference yield:

allyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside (10343-15-4,39698-55-0,78730-32-2,119111-31-8,119111-32-9,54400-76-9) → allyl 3-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside (400090-99-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium methylate / methanol / 0.5 h / 20 °C

1.2: Dowex 50 acidic resin / 20 °C

2.1: camphor-10-sulfonic acid / acetonitrile / 20 °C

3.1: 18-crown-6 ether; potassium hydroxide / tetrahydrofuran / 0.33 h

With 18-crown-6 ether; camphor-10-sulfonic acid; sodium methylate; potassium hydroxide; In tetrahydrofuran; methanol; acetonitrile;

DOI:10.1002/ejoc.201101539

upstream raw materials:

benzyl bromide

allyl 4,6-O-(S)-benzylidene-β-D-galactopyranoside

allyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside

allyl β-D-galactopyranoside

Downstream raw materials:

(2R)-2,3-dihydroxypropyl 3-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside

(2S)-2,3-dihydroxypropyl 3-O-benzyl-4,6-O-(S)-benzylidene-β-D-galactopyranoside

allyl 2-O-benzoyl-3,6-di-O-benzyl-β-D-galactopyranoside

allyl 2-O-benzoyl-3-O-benzyl-4,6-O-benzylidene-β-D-galactopyranoside