Benzyl 4,6-O-benzylidene-alpha-D-galactopyranoside

Base Information

• Chemical Name: Benzyl 4,6-O-benzylidene-alpha-D-galactopyranoside
• CAS No.: 57783-86-5
• Molecular Formula: C₂₀H₂₂O₆
• Molecular Weight: 358.391
• Mol file: 57783-86-5.mol

Synonyms:BENZYL 4,6-O-BENZYLIDENE-ALPHA-D-GALACTOPYRANOSIDE;Benzyl4,6-O-benzylidene-a-D-galactopyranoside

Chemical Property of Benzyl 4,6-O-benzylidene-alpha-D-galactopyranoside

Chemical Property:

• Boiling Point: 557.0±50.0 °C(Predicted)
• PKA: 12.80±0.70(Predicted)
• PSA: 77.38000
• Density: 1.34±0.1 g/cm3(Predicted)
• LogP: 1.76410

Purity/Quality:

99% ^*data from raw suppliers

Benzyl 4,6-O-benzylidene-a-D-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Benzyl 4,6-O-Benzylidene-alpha-d-galactopyranoside is a useful intermediate for organic synthesis.

Technology Process of Benzyl 4,6-O-benzylidene-alpha-D-galactopyranoside

There total 24 articles about Benzyl 4,6-O-benzylidene-alpha-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: 86.0%

benzaldehyde dimethyl acetal (1125-88-8) + (2R,3R,4S,5S,6R)-2-(benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol (4304-12-5) → benzyl 4,6-O-benzylidene-β-D-glucopyranoside (30607-98-8,35905-28-3,40983-94-6,56341-65-2,57783-86-5,58006-32-9,72869-10-4,73366-72-0,79549-73-8,110850-30-1,113973-86-7,117895-05-3)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 80 ℃; for 2.5h; Inert atmosphere;

DOI:10.1039/c2ob25065a

Reference yield: 85.0%

benzyl D-glucopyranoside (34246-23-6) + benzaldehyde dimethyl acetal (1125-88-8) → benzyl 4,6-O-(phenylmethylene)-α-D-glucopyranoside (79549-73-8) + benzyl 4,6-O-benzylidene-β-D-glucopyranoside (30607-98-8,35905-28-3,40983-94-6,56341-65-2,57783-86-5,58006-32-9,72869-10-4,73366-72-0,79549-73-8,110850-30-1,113973-86-7,117895-05-3)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.9b04279

Reference yield: 64.0%

benzyl 2-O-acetyl-4,6-O-benzylidene-3-O-tosyl-β-D-glucopyranoside (83050-00-4) → benzyl 4,6-O-benzylidene-β-D-glucopyranoside (30607-98-8,35905-28-3,40983-94-6,56341-65-2,57783-86-5,58006-32-9,72869-10-4,73366-72-0,79549-73-8,110850-30-1,113973-86-7,117895-05-3) + benzyl 4,6-O-benzylidene-3-deoxy-β-D-ribo-hexopyranoside (234083-58-0)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; water; ethyl acetate; for 7h; Heating;

DOI:10.1016/S0008-6215(00)82220-X

upstream raw materials:

(2R,3R,4S,5S,6R)-2-(benzyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

benzyl D-glucopyranoside

benzaldehyde dimethyl acetal

benzyl 2-O-acetyl-4,6-O-benzylidene-3-O-tosyl-β-D-glucopyranoside

Downstream raw materials:

benzyl 2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

benzyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

benzyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside

benzyl 2-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside