2-O-alpha-L-Rhamnopyranosyl-D-glucopyranose

Base Information

• Chemical Name: 2-O-alpha-L-Rhamnopyranosyl-D-glucopyranose
• CAS No.: 19949-48-5
• Molecular Formula: C₁₂H₂₂O₁₀
• Molecular Weight: 326.301
• DSSTox Substance ID: DTXSID20937829
• Nikkaji Number: J3.288.339G
• Wikipedia: Neohesperidose
• Wikidata: Q3347120
• Metabolomics Workbench ID: 68826
• Mol file: 19949-48-5.mol

Synonyms:Neohesperidose;2-O-alpha-L-Rhamnopyranosyl-D-glucopyranose;C08244;Neohesperidoside;alpha-L-rhamnopyranosyl-(1->2)-beta-D-glucopyranose;AC1L9B54;beta-Neohesperidose;SureCN6521257;Ambap17074-02-1;SCHEMBL6521257;CHEBI:73992;2-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranose;DTXSID20937829;MFCD00064919;alpha-L-Rhap-(1->2)-beta-D-Glcp;2-O-alpha-l-rhamnosyl-beta-d-glucose;2-O-(6-Deoxyhexopyranosyl)hexopyranose;2-O-(alpha-L-rhamnopyranosyl)-beta-D-glucopyranose;Q3347120;6-deoxy-alpha-L-mannopyranosyl-(1->2)-beta-D-glucopyranose;WURCS=2.0/2,2,1/[a2122h-1b_1-5][a2211m-1a_1-5]/1-2/a2-b1;(2R,3R,4S,5S,6R)-6-(hydroxymethyl)-3-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)tetrahydro-2H-pyran-2,4,5-triol;(2S,3R,4R,5R,6S)-2-methyl-6-[(2R,3R,4S,5S,6R)-2,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-3-yl]oxy-tetrahydropyran-3,4,5-triol

Chemical Property of 2-O-alpha-L-Rhamnopyranosyl-D-glucopyranose

Chemical Property:

• XLogP3: -3.7
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 3
• Exact Mass: 326.12129689
• Heavy Atom Count: 22
• Complexity: 368

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC2C(C(C(OC2O)CO)O)O)O)O)O
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H](O[C@H]2O)CO)O)O)O)O)O

Technology Process of 2-O-alpha-L-Rhamnopyranosyl-D-glucopyranose

There total 17 articles about 2-O-alpha-L-Rhamnopyranosyl-D-glucopyranose 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: 72.9%

benzyl 2-O-α-L-rhamnopyranosyl-β-D-galactopyranoside (80832-23-1) → 2-O-α-L-rhamnopyranosyl-D-galactopyranose (2781-65-9,16741-18-7,19949-48-5,36476-16-1,80876-56-8,137171-16-5,137171-17-6,137171-18-7,137171-19-8,146076-26-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; water; acetic acid; for 12h; Ambient temperature;

DOI:10.1016/S0008-6215(00)80970-2

Reference yield:

neohesperidin (13241-33-3,61303-28-4,61303-29-5,61303-30-8,61347-97-5,61348-24-1,88294-38-6,139686-38-7) → 2-O-α-L-rhamnopyranosyl-β-D-glucopyranose (19949-48-5) + hesperetin (520-33-2,41001-90-5,69097-99-0)

Guidance literature:

With sulfuric acid; In methanol; water; for 6h; Reflux;

DOI:10.1016/j.foodchem.2010.12.129

Reference yield:

naringin (10236-47-2) → 2-O-α-L-rhamnopyranosyl-β-D-glucopyranose (19949-48-5) + naringenin (480-41-1)

Guidance literature:

With sulfuric acid; In methanol; water; for 6h; Reflux;

DOI:10.1016/j.foodchem.2010.12.129

upstream raw materials:

neohesperidin

naringin

benzyl 2-O-α-L-rhamnopyranosyl-β-D-galactopyranoside

sophoraflavoside I

Downstream raw materials:

L-Rhamnose

D-Galactose

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