PHENYL 2,3,4,5-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE

Base Information

• Chemical Name: PHENYL 2,3,4,5-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE
• CAS No.: 3427-45-0
• Molecular Formula: C20H24 O10
• Molecular Weight: 424.405
• Hs Code.: 29400090
• Mol file: 3427-45-0.mol

Synonyms:Glucopyranoside,phenyl, tetraacetate, a-D- (8CI); Phenyl 2,3,4,6-tetra-O-acetyl-a-D-glucopyranoside; Phenyl tetra-O-acetyl-a-D-glucopyranoside; Phenyl a-D-glucopyranoside tetraacetate

Chemical Property of PHENYL 2,3,4,5-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE

Chemical Property:

• Melting Point: 115 °C
• Boiling Point: 491.4±45.0 °C(Predicted)
• PSA: 123.66000
• Density: 1.29±0.1 g/cm3(Predicted)
• LogP: 1.14850
• Storage Temp.: −20°C

Purity/Quality:

98%min ^*data from raw suppliers

Phenyl 2,3,4,6-tetra-O-acetyl-a-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of PHENYL 2,3,4,5-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE

There total 32 articles about PHENYL 2,3,4,5-TETRA-O-ACETYL-ALPHA-D-GLUCOPYRANOSIDE 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: 76.0%

2,3,4,6-tetra-O-acetyl-1-O-trifluoroacetyl-β-D-glucopyranose (78942-85-5) + phenol (108-95-2,27073-41-2) → phenyl 2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside (3427-45-0)

Guidance literature:

With boron trifluoride diethyl etherate; In benzene; for 1.5h; Heating;

DOI:10.1023/A:1019532924135

Reference yield: 75.0%

triphenylborane (1095-03-0) + per-O-acetyl-α-D-mannopyranose (4163-65-9) → phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (2872-72-2,3427-45-0,4468-72-8,18463-30-4,30657-71-7,37797-55-0,37797-56-1,39031-66-8,39031-67-9,94798-88-6)

Guidance literature:

ytterbium(III) triflate; at 20 ℃; for 48h;

DOI:10.1016/S0040-4039(01)00644-X

Reference yield: 58.1%

phenol (108-95-2,27073-41-2) + β-D-mannopyranose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → phenyl α-2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (2872-72-2,3427-45-0,4468-72-8,18463-30-4,30657-71-7,37797-55-0,37797-56-1,39031-66-8,39031-67-9,94798-88-6)

Guidance literature:

With tin(IV) chloride; In benzene; for 1h; Mechanism; Heating;

upstream raw materials:

phenol

methyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside

β-D-mannopyranose pentaacetate

per-O-acetyl-α-D-mannopyranose

Downstream raw materials:

phenyl α-D-mannoopyranoside

phenyl-α-D-talopyranoside

Phenyl-(tetra-O-methyl-α-D-glucopyranosid)

1-O-(4′-bromophenyl)-2,3,4,6-tetra-O-acetyl-α-D-glucopyranoside

Refernces

• 1、 Dimakos, Victoria,Liu, Jacklyn J. W.,Ge, Zhenlu,Taylor, Mark S.. "Copper-mediated anomeric: O -arylation with organoboron reagents". supporting information. p. 5671 - 5674. Retrieved 2019/06/18.
• 2、 Bergeron-Brlek, Milan,Giguere, Denis,Shiao, Tze Chieh,Saucier, Catherine,Roy, Rene. "Palladium-catalyzed ullmann-type reductive homocoupling of iodoaryl glycosides". scheme or table. p. 2971 - 2977. Retrieved 2012/05/04.