PENT-4-ENYL-2,3,4-TRI-O-BENZYL-D-GLUCO PYRANOSIDE

Base Information

• Chemical Name: PENT-4-ENYL-2,3,4-TRI-O-BENZYL-D-GLUCO PYRANOSIDE
• CAS No.: 155036-27-4
• Molecular Formula: C32H38 O6
• Molecular Weight: 518.65
• Mol file: 155036-27-4.mol

Synonyms:b-D-Glucopyranoside, 4-pentenyl2,3,4-tris-O-(phenylmethyl)- (9CI)

Chemical Property of PENT-4-ENYL-2,3,4-TRI-O-BENZYL-D-GLUCO PYRANOSIDE

Chemical Property:

• Vapor Pressure: 5.07E-17mmHg at 25°C
• Refractive Index: 1.585
• Boiling Point: 635.5°Cat760mmHg
• Flash Point: 338.1°C
• PSA: 66.38000
• Density: 1.16g/cm³
• LogP: 5.44260

Purity/Quality:

PENT-4-ENYL-2,3,4-TRI-OXY-BENZYL-D-GLUCO PYRANOSIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of PENT-4-ENYL-2,3,4-TRI-O-BENZYL-D-GLUCO PYRANOSIDE

There total 5 articles about PENT-4-ENYL-2,3,4-TRI-O-BENZYL-D-GLUCO PYRANOSIDE 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: 99.0%

n-pent-4-yl 2,3,4-O-tribenzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside (127570-60-9) → pent-4-enyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside (155036-27-4)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃;

DOI:10.1002/ejoc.201001278

Reference yield:

pent-4-enyl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-β-D-glucopyranoside (144368-75-2) → pent-4-enyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside (155036-27-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; water;

DOI:10.1021/jo071191s

Reference yield:

C27H38O6Si (127570-63-2) → pent-4-enyl 2,3,4-tri-O-benzyl-β-D-glucopyranoside (155036-27-4)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 20 °C

With tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201001278

upstream raw materials:

pent-4-enyl 2,3,4-tri-O-benzyl-6-O-triphenylmethyl-β-D-glucopyranoside

C₂₇H₃₈O₆Si

n-pent-4-yl 2,3,4-O-tribenzyl-6-O-(tert-butyldiphenylsilyl)-β-D-glucopyranoside

n-pent-4-enyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

Downstream raw materials:

4-pentenyl 6-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

C₅₃H₅₉NO₁₃

C₅₃H₅₉NO₁₃

C₃₃H₃₇ClO₈

Refernces

• 1、 Kamat, Medha N.,De Meo, Cristina,Demchenko, Alexei V.. "S-benzoxazolyl as a stable protecting moiety and a potent anomeric leaving group in oligosaccharide synthesis". . p. 6947 - 6955. Retrieved 2008/02/11.