1,5-ANHYDRO-4,6-O-BENZYLIDENE-2-O-P-TOLUOYL-D-GLUCITOL

Base Information

• Chemical Name: 1,5-ANHYDRO-4,6-O-BENZYLIDENE-2-O-P-TOLUOYL-D-GLUCITOL
• CAS No.: 156715-23-0
• Molecular Formula: C₂₁H₂₂O₆
• Molecular Weight: 370.402
• Mol file: 156715-23-0.mol

Synonyms:Pyrano[3,2-d]-1,3-dioxin,D-glucitol deriv.

Chemical Property of 1,5-ANHYDRO-4,6-O-BENZYLIDENE-2-O-P-TOLUOYL-D-GLUCITOL

Chemical Property:

• Boiling Point: 558.6±50.0 °C(Predicted)
• PKA: 12.63±0.60(Predicted)
• PSA: 74.22000
• Density: 1.31±0.1 g/cm3(Predicted)
• LogP: 2.39430

Purity/Quality:

99%min ^*data from raw suppliers

1,5-Anhydro-4,6-O-benzylidene-2-O-toluoyl-D-glucitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 1,5-ANHYDRO-4,6-O-BENZYLIDENE-2-O-P-TOLUOYL-D-GLUCITOL is an useful synthetic intermediate in the preparation of sugar nucleotides.

Technology Process of 1,5-ANHYDRO-4,6-O-BENZYLIDENE-2-O-P-TOLUOYL-D-GLUCITOL

There total 3 articles about 1,5-ANHYDRO-4,6-O-BENZYLIDENE-2-O-P-TOLUOYL-D-GLUCITOL 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:

1,5-anhydro-D-glucitol (154-58-5,53319-04-3) → 1,5-anhydro-4,6-O-benzylidene-2-O-(p-toluoyl)-D-glucitol (156715-23-0)

Guidance literature:

Multi-step reaction with 2 steps

1: ZnCl₂ / 48 h / Ambient temperature

2: 1.) dibutyltin oxide / 1.) benzene, reflux, 16 h, 2.) dioxane, RT, 5 h

With di(n-butyl)tin oxide; zinc(II) chloride;

DOI:10.1021/jm00066a013

Reference yield:

1-deoxy-D-glucose tetraacetate (13137-69-4) → 1,5-anhydro-4,6-O-benzylidene-2-O-(p-toluoyl)-D-glucitol (156715-23-0)

Guidance literature:

Multi-step reaction with 3 steps

1: NaOMe / 2 h / Ambient temperature

2: ZnCl₂ / 48 h / Ambient temperature

3: 1.) dibutyltin oxide / 1.) benzene, reflux, 16 h, 2.) dioxane, RT, 5 h

With sodium methylate; di(n-butyl)tin oxide; zinc(II) chloride;

DOI:10.1021/jm00066a013

Reference yield:

4-methyl-benzoyl chloride (874-60-2) + (4aR,7S,8R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol (65190-39-8) → 1,5-anhydro-4,6-O-benzylidene-2-O-(p-toluoyl)-D-glucitol (156715-23-0)

Guidance literature:

With di(n-butyl)tin oxide; Yield given. Multistep reaction; 1.) benzene, reflux, 16 h, 2.) dioxane, RT, 5 h;

DOI:10.1021/jm00066a013

upstream raw materials:

4-methyl-benzoyl chloride

(4aR,7S,8R,8aS)-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol

1,5-anhydro-D-glucitol

1-deoxy-D-glucose tetraacetate

Refernces