1,2,3,6-Tetra-O-benzyl-b-D-glucopyranoside

Base Information

• Chemical Name: 1,2,3,6-Tetra-O-benzyl-b-D-glucopyranoside
• CAS No.: 67831-42-9
• Molecular Formula: C34H36O6
• Molecular Weight: 540.656
• Mol file: 67831-42-9.mol

Synonyms:1,2,3,6-Tetra-O-benzyl-b-D-glucopyranoside;PhenylMethyl 2,3,6-Tris-O-(phenylMethyl)-β-D-glucopyranoside

Chemical Property of 1,2,3,6-Tetra-O-benzyl-b-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 60.4-64.4 °C
• Boiling Point: 676.061°C at 760 mmHg
• PKA: 12.92±0.70(Predicted)
• Flash Point: 362.669°C
• PSA: 66.38000
• Density: 1.222g/cm³
• LogP: 5.67660
• Storage Temp.: Refrigerator
• Solubility.: Dichloromethane, Ethyl Acetate

Purity/Quality:

98%Min ^*data from raw suppliers

1,2,3,6-Tetra-O-benzyl-b-D-glucopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,2,3,6-Tetra-O-benzyl-b-D-glucopyranoside

There total 21 articles about 1,2,3,6-Tetra-O-benzyl-b-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: 95.0%

benzyl 4,6-O-benzylidene-2,3-tri-O-benzyl-β-D-glucopyranoside (57783-66-1) → benzyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside (67831-42-9)

Guidance literature:

With triethylsilane; trifluoroacetic acid; In dichloromethane;

DOI:10.1246/bcsj.71.2893

Reference yield: 88.0%

benzyl 2,3-di-O-benzyl-6-O-tosyl-β-D-glucopyranoside (74352-49-1) + sodium phenyl-methanolate (20194-18-7) → benzyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside (67831-42-9)

Guidance literature:

In N,N-dimethyl-formamide; benzyl alcohol; at 90 ℃; for 2h;

DOI:10.1016/S0008-6215(00)85527-5

Reference yield: 85.0%

benzyl 4,6-O-benzylidene-2,3-tri-O-benzyl-β-D-glucopyranoside (57783-66-1) → benzyl 2,3,4-tri-O-benzyl-D-glucopyranoside (27851-29-2) + benzyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside (67831-42-9)

Guidance literature:

With hydrogenchloride; 3 A molecular sieve; sodium cyanoborohydride; In tetrahydrofuran; diethyl ether; at 0 ℃; for 1h;

DOI:10.1016/0008-6215(83)84014-2

upstream raw materials:

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

benzyl 2,3-di-O-benzyl-6-O-tosyl-β-D-glucopyranoside

sodium phenyl-methanolate

benzyl bromide

Downstream raw materials:

(1R,2R,3S,4S,5R)-3,4-Bis-allyloxy-2-benzyloxy-6,8-dioxa-bicyclo[3.2.1]octane

benzyl O-(2,3-di-O-allyl-4,6-di-O-benzyl-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

benzyl O-(2,3-di-O-allyl-4,6-di-O-benzyl-α-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-β-D-glucopyranoside

C₆₁H₆₄O₁₀

Refernces

• 1、 Matovi?, Jelena,J?rvinen, Juulia,Sokka, Iris K.,Imlimthan, Surachet,Raitanen, Jan-Erik,Montaser, Ahmed,Maaheimo, Hannu,Huttunen, Kristiina M.,Per?niemi, Sirpa,Airaksinen, Anu J.,Sarparanta, Mirkka,Johansson, Mikael P.,Rautio, Jarkko,Ekholm, Filip S.. "Exploring the Biochemical Foundations of a Successful GLUT1-Targeting Strategy to BNCT: Chemical Synthesis and in Vitro Evaluation of the Entire Positional Isomer Library of ortho-Carboranylmethyl-Bearing Glucoconjugates". . p. 285 - 304. Retrieved 2020/12/21.
• 2、 Hirooka, Motoko,Koto, Shinkiti. "Dehydrative glycosylation by diethylaminosulfur trifluoride (DAST) - tin(II) trifluoromethanesulfonate-tetrabutylammonium perchlorate - triethylamine system". . p. 2893 - 2902. Retrieved 2007/10/03.