2-Propenyl glucopyranoside

Base Information

• Chemical Name: 2-Propenyl glucopyranoside
• CAS No.: 48149-74-2
• Molecular Formula: C₉H₁₆O₆
• Molecular Weight: 220.222
• DSSTox Substance ID: DTXSID201303530
• Mol file: 48149-74-2.mol

Synonyms:2-propenyl glucopyranoside;SCHEMBL169375;2-Propen-1-yl D-glucopyranoside;DTXSID201303530;48149-74-2

Chemical Property of 2-Propenyl glucopyranoside

Chemical Property:

• Boiling Point: 415.0±45.0 °C(Predicted)
• Density: 1.37±0.1 g/cm3(Predicted)
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 4
• Exact Mass: 220.09468823
• Heavy Atom Count: 15
• Complexity: 209

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C=CCOC1C(C(C(C(O1)CO)O)O)O
• Isomeric SMILES: C=CCOC1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O

Technology Process of 2-Propenyl glucopyranoside

There total 33 articles about 2-Propenyl 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: 99.0%

Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester (10343-15-4,39698-55-0,54400-76-9,78730-32-2,119111-31-8,119111-32-9) → allyl β-D-glucopyranoside (2595-07-5,7464-56-4,34384-79-7,41308-76-3,48149-72-0,48149-74-2,85249-43-0,119479-69-5,821794-45-0)

Guidance literature:

With ammonium hydroxide; In methanol; for 19h; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.201701238

Reference yield: 95.0%

allyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside → allyl β-D-glucopyranoside (2595-07-5,7464-56-4,34384-79-7,41308-76-3,48149-72-0,48149-74-2,85249-43-0,119479-69-5,821794-45-0)

Guidance literature:

With sodium methylate; In methanol; Inert atmosphere;

DOI:10.1021/acs.joc.0c01404

Reference yield: 85.0%

D-Galactose (10257-28-0) + allyl alcohol (107-18-6) → allyl D-galactopyranoside (2595-07-5,7464-56-4,34384-79-7,41308-76-3,48149-72-0,48149-74-2,85249-43-0,119479-69-5,821794-45-0)

Guidance literature:

allyl alcohol; With acetyl chloride; at 0 ℃; for 0.5h; Inert atmosphere;

D-Galactose; at 25 - 80 ℃; Inert atmosphere;

DOI:10.1039/d0ob02176h

upstream raw materials:

D-Glucose

allyl alcohol

Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester

D-glucose pentaacetate

Downstream raw materials:

allyl 4,6-O-benzylidene-β-D-glucopyranoside

allyl 4,6-O-(4-methoxybenzylidene)-β-D-glucopyranoside

Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester

Refernces

• 1、 Dey, Kalyan,Jayaraman, Narayanaswamy. "Anomeric alkylations and acylations of unprotected mono- and disaccharides mediated by pyridoneimine in aqueous solutions". supporting information. p. 2224 - 2227. Retrieved 2022/02/17.
• 2、 Ardá, Ana,Blériot, Yves,Bordes, Alexandra,Désiré, Jér?me,Franconetti, Antonio,Guillard, Jer?me,Jiménez-Barbero, Jesús,Ménand, Micka?l,Perrin, Flavie,Poveda, Ana,Sollogoub, Matthieu,Tripier, Rapha?l,Troadec, Thibault. "Synthesis, Conformational Analysis, and Complexation Study of an Iminosugar-Aza-Crown, a Sweet Chiral Cyclam Analog". supporting information. . Retrieved 2020/03/26.