4,6-O-BENZYLIDENE-D-GLUCOPYRANOSE

Base Information

• Chemical Name: 4,6-O-BENZYLIDENE-D-GLUCOPYRANOSE
• CAS No.: 30688-66-5
• Molecular Formula: C13H16O6
• Molecular Weight: 268.2625
• Hs Code.: 2912499000
• Mol file: 30688-66-5.mol

Synonyms:D-Glucose,4,6-O-benzylidene- (7CI,8CI);4,6-O-Benzylidene-D-glucose;(2R,3R)-2,3-dihydroxy-3-[(4R,5R)-5-hydroxy-2-phenyl-1,;4,6-Benzylidene-D-glucose;D-Glucose, 4,6-O-(phenylmethylene)-;

Chemical Property of 4,6-O-BENZYLIDENE-D-GLUCOPYRANOSE

Chemical Property:

• Vapor Pressure: 1.05E-11mmHg at 25°C
• Melting Point: 183-186 °C
• Refractive Index: 1.58
• Boiling Point: 521.6 °C at 760 mmHg
• PKA: 12.44±0.20(Predicted)
• Flash Point: 201.7 °C
• PSA: 88.38000
• Density: 1.379 g/cm³
• LogP: -0.46040
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C

Purity/Quality:

98% ^*data from raw suppliers

4,6-O-Benzylidene-D-glucopyranose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Description: 4,6-O-Benzylidene-D-glucose is a useful intermediate for the synthesis of carbohydrates.

Technology Process of 4,6-O-BENZYLIDENE-D-GLUCOPYRANOSE

There total 5 articles about 4,6-O-BENZYLIDENE-D-GLUCOPYRANOSE 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: 83.0%

D-Glucose (2280-44-6) + benzaldehyde dimethyl acetal (1125-88-8) → 4,6-O-benzylidene-D-glucopyranose (30688-66-5,3006-41-5,20771-09-9,25152-90-3,97232-16-1,104022-77-7,113566-67-9,113566-68-0)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2011.09.130

Reference yield: 48.0%

D-Glucose (2280-44-6) + benzaldehyde (100-52-7) → 4,6-O-benzylidene-D-glucopyranose (30688-66-5,3006-41-5,20771-09-9,25152-90-3,97232-16-1,104022-77-7,113566-67-9,113566-68-0)

Guidance literature:

With zinc(II) chloride; for 4h; Ambient temperature;

DOI:10.1021/jo00113a038

Reference yield:

D-glucose (50-99-7) + benzaldehyde dimethyl acetal (1125-88-8) → 4,6-O-benzylidene-D-glucopyranose (30688-66-5,3006-41-5,20771-09-9,25152-90-3,97232-16-1,104022-77-7,113566-67-9,113566-68-0)

Guidance literature:

With toluene-4-sulfonic acid; In N,N-dimethyl-formamide; at 70 ℃;

DOI:10.1016/S0008-6215(97)00148-1

upstream raw materials:

D-Glucose

benzaldehyde

alpha-D-glucopyranose

benzaldehyde dimethyl acetal

Refernces

• 1、 Gut, Bartosz,Mlynarski, Jacek. "Tertiary Amine Promoted Asymmetric Aldol Reaction of Aldehydes". supporting information. p. 5075 - 5078. Retrieved 2015/08/18.
• 2、 Sanhueza, Carlos A.,Dorta, Rosa L.,Vazquez, Jesus T.. "Involvement of the S-aglycon in the conformational preferences of thioglucosides". . p. 258 - 264. Retrieved 2008/09/19.