Methyl alpha-L-rhamnopyranoside

Base Information

• Chemical Name: Methyl alpha-L-rhamnopyranoside
• CAS No.: 14917-55-6
• Molecular Formula: C7H14 O5
• Molecular Weight: 178.185
• Hs Code.: 29400090
• European Community (EC) Number: 238-987-7
• DSSTox Substance ID: DTXSID901310495
• Nikkaji Number: J227.230J
• Wikidata: Q27464881
• Mol file: 14917-55-6.mol

Synonyms:methyl 6-deoxymannopyranoside;methyl rhamnopyranoside

Chemical Property of Methyl alpha-L-rhamnopyranoside

Chemical Property:

• Vapor Pressure: 4.59E-05mmHg at 25°C
• Melting Point: 108-109°C
• Boiling Point: 312.6°Cat760mmHg
• PKA: 13.05±0.70(Predicted)
• Flash Point: 142.9°C
• PSA: 79.15000
• Density: 1.32g/cm³
• LogP: -1.53970
• Storage Temp.: 2-8°C
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 1
• Exact Mass: 178.08412354
• Heavy Atom Count: 12
• Complexity: 151

Purity/Quality:

99%, ^*data from raw suppliers

Methyl a-L-rhamnopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(C(C(C(O1)OC)O)O)O
• Isomeric SMILES: C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC)O)O)O

Technology Process of Methyl alpha-L-rhamnopyranoside

There total 136 articles about Methyl alpha-L-rhamnopyranoside 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%

methanol (67-56-1) + L-rhamnose (73-34-7) → methyl 6-deoxy-α-L-mannopyranoside (14917-55-6)

Guidance literature:

With ion-exchange resin Dowex 50X₈-100; hydrogen cation; for 24h; Heating;

Reference yield: 90.0%

methyl 2-O-(fluoren-9-yl)-α-L-rhamnopyranoside (137017-00-6) → methyl 6-deoxy-α-L-mannopyranoside (14917-55-6)

Guidance literature:

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

DOI:10.1016/0008-6215(92)84177-T

Reference yield: 90.0%

methanol (67-56-1) + L-Rhamnose (3615-41-6,478518-52-4) → methyl 6-deoxy-α-L-mannopyranoside (14917-55-6)

Guidance literature:

With molecular sieve; Amberlite IR-120 (H⁺); for 16h; Heating;

upstream raw materials:

methanol

L-Fucose

6-deoxy-L-galactose

methyl-2,3-di-O-acetyl-4-O-benzoyl-6-desoxy-α-D-arabino-hex-5-enopyranoside

Downstream raw materials:

L-galacto-2,4,5-Trihydroxy-3-methoxy-hexanal

methyl 2,3,4-tri-O-benzoyl α-L-rhamnopyranoside

methyl 2,3-O-isopropylidene-α-L-rhamnoside

methyl-α-DL-rhamnopyranoside

Refernces

• 1、 Nakae, Koichi,Kurata, Ikuko,Kojima, Fukiko,Igarashi, Masayuki,Hatano, Masaki,Sawa, Ryuichi,Kubota, Yumiko,Adachi, Hayamitsu,Nomoto, Akio. "Sacchathridine A, a prostaglandin release inhibitor from Saccharothrix sp.". . p. 720 - 722. Retrieved 2013.
• 2、 Carder, Hayden M.,Suh, Carolyn E.,Wendlandt, Alison E.. "A Unified Strategy to Access 2- And 4-Deoxygenated Sugars Enabled by Manganese-Promoted 1,2-Radical Migration". supporting information. p. 13798 - 13805. Retrieved 2021/09/07.
• 3、 Khatri, Hem Raj,Bhattarai, Bijay,Kaplan, Will,Li, Zhongzheng,Curtis Long, Marcus John,Aye, Yimon,Nagorny, Pavel. "Modular Total Synthesis and Cell-Based Anticancer Activity Evaluation of Ouabagenin and Other Cardiotonic Steroids with Varying Degrees of Oxygenation". supporting information. p. 4849 - 4860. Retrieved 2019/03/26.