PENT-4-ENYL-2,3,46-TETRA-O-BENZYL-D-GLUCOPYRANOSIDE

Base Information

• Chemical Name: PENT-4-ENYL-2,3,46-TETRA-O-BENZYL-D-GLUCOPYRANOSIDE
• CAS No.: 113533-73-6
• Molecular Formula: C39H44 O6
• Molecular Weight: 608.775
• Mol file: 113533-73-6.mol

Synonyms:b-D-Glucopyranoside, 4-pentenyl2,3,4,6-tetrakis-O-(phenylmethyl)- (9CI)

Chemical Property of PENT-4-ENYL-2,3,46-TETRA-O-BENZYL-D-GLUCOPYRANOSIDE

Chemical Property:

• Vapor Pressure: 1.81E-18mmHg at 25°C
• Melting Point: 70-71 °C(Solv: dichloromethane (75-09-2); hexane (110-54-3))
• Refractive Index: 1.592
• Boiling Point: 696.8°Cat760mmHg
• Flash Point: 256.2°C
• PSA: 55.38000
• Density: 1.15g/cm³
• LogP: 7.66710

Purity/Quality:

95% ^*data from raw suppliers

PENT-4-ENYL-2,3,4,6-TETRA-O-BENZYL-D-GLUCOPYRANOSIDE 98.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of PENT-4-ENYL-2,3,46-TETRA-O-BENZYL-D-GLUCOPYRANOSIDE

There total 16 articles about PENT-4-ENYL-2,3,46-TETRA-O-BENZYL-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%

(2R,3R,4S,5R,6S)-3,4,5-tris(benzyloxy)-2-(benzyloxymethyl)-6-(prop-2-ynyloxy)tetrahydro-2H-pyran (194088-19-2) + n-Pent-4-enyl alcohol (821-09-0) → (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran (113533-73-6)

Guidance literature:

With FeCl₃/C; In acetonitrile; at 60 ℃; for 8h; stereoselective reaction; Inert atmosphere; Green chemistry;

DOI:10.1055/s-0037-1611801

Reference yield: 90.0%

n-Pent-4-enyl alcohol (821-09-0) + 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (74808-09-6) → (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran (113533-73-6)

Guidance literature:

With gold(III) chloride; In dichloromethane; at -70 ℃; for 0.5h; diastereoselective reaction; Molecular sieve; Inert atmosphere; Schlenk technique; Darkness;

DOI:10.1021/jacs.5b07895

Reference yield: 89.0%

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide (4196-35-4) + n-Pent-4-enyl alcohol (821-09-0) → (2R,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-(pent-4-en-1-yloxy)tetrahydro-2H-pyran (113533-73-6)

Guidance literature:

With sodium hydride; In dichloromethane;

DOI:10.1016/j.tetlet.2007.12.105

upstream raw materials:

benzyl bromide

pent-4-enyl α,β-D-glucopyranoside

4-penten-1-yl-β-D-glucopyranoside

D-Glucose

Downstream raw materials:

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1→3)-1,2:5,6-di-O-isopropylidene-α-D-glucofuranoside

1,2:5,6-di-O-isopropylidene-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1-3)-α-D-glucofuranose

methyl 2,3,4,6-tetra-O-benzyl-D-glucopyranoside

3-formylpropyl 2,3,4,6-tetra-O-benzyl-β-D-glucopyranoside