(2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Base Information

• Chemical Name: (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol
• CAS No.: 2595-07-5
• Molecular Formula: C9H16O6
• Molecular Weight: 220.222
• Hs Code.: 2932999099
• ChEMBL ID: CHEMBL4213920
• Nikkaji Number: J36.667F
• Mol file: 2595-07-5.mol

Synonyms:allyl galactopyranoside

Chemical Property of (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

Chemical Property:

• Vapor Pressure: 1.27E-08mmHg at 25°C
• Refractive Index: 1.549
• Boiling Point: 415 °C at 760 mmHg
• Flash Point: 204.8 °C
• PSA: 99.38000
• Density: 1.37g/cm³
• LogP: -2.01110
• Storage Temp.: 2-8°C
• 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:

98% ^*data from raw suppliers

Allyl b-D-galactopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C=CCOC1C(C(C(C(O1)CO)O)O)O
• Isomeric SMILES: C=CCO[C@H]1[C@@H]([C@H]([C@H]([C@H](O1)CO)O)O)O

Technology Process of (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol

There total 49 articles about (2R,3R,4S,5R,6R)-2-(Allyloxy)-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol 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 (R)-4,6-O-benzylidene-β-D-gluco-pyranoside

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

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

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