2-O-methylrhamnose

Base Information

• Chemical Name: 2-O-methylrhamnose
• CAS No.: 17212-17-8
• Molecular Formula: C₇H₁₄O₅
• Molecular Weight: 178.185
• Mol file: 17212-17-8.mol

Synonyms:Mannose,6-deoxy-2-O-methyl-, D- (8CI); 2-O-Methyl-D-rhamnose

Chemical Property of 2-O-methylrhamnose

Chemical Property:

• Vapor Pressure: 1.4E-07mmHg at 25°C
• Boiling Point: 386.8°Cat760mmHg
• Flash Point: 159.7°C
• PSA: 86.99000
• Density: 1.256g/cm³
• LogP: -1.69710

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-O-methylrhamnose

There total 12 articles about 2-O-methylrhamnose 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: 43.0%

allyl 2-O-methyl-α-L-fucopyranoside (108182-36-1) → 2-O-methyl-L-fucose (921-90-4,4060-14-4,4060-15-5,17212-17-8,22350-97-6,29839-06-3,56192-98-4,88853-34-3,34299-00-8)

Guidance literature:

With methanol; palladium dichloride; In dichloromethane; at 20 ℃; for 24h; Inert atmosphere;

DOI:10.3762/bjoc.12.282

Reference yield:

O-polysaccharide of the lipopolysaccharide from Azospirillum brasilense Jm6B2 + methyl iodide (74-88-4) → 2,3-di-O-methylxylose (6778-35-4,7459-37-2,13403-20-8,39951-09-2,101468-34-2,4153-29-1) + 2-O-methyl-L-fucose (921-90-4,4060-14-4,4060-15-5,17212-17-8,22350-97-6,29839-06-3,56192-98-4,88853-34-3,34299-00-8) + 6-deoxy-3,4-di-O-methylhexose + 6-deoxy-3-O-methylhexose (149655-76-5,18546-13-9) + 2,3,4,6-tetra-O-methylhexose + 2,3-di-O-methylhexose + 2,3,4-tri-O-methylrhamnose (890026-66-1)

Guidance literature:

O-polysaccharide of the lipopolysaccharide from Azospirillum brasilense Jm₆B₂; methyl iodide; With sodium hydroxide; In dimethyl sulfoxide;

With water; trifluoroacetic acid; at 100 ℃; for 2h;

DOI:10.1016/j.carres.2012.04.006

Reference yield:

allyl 3,4-di-O-isopropylidene-α-L-fucopyranoside (108182-34-9) → 2-O-methyl-L-fucose (921-90-4,4060-14-4,4060-15-5,17212-17-8,22350-97-6,29839-06-3,56192-98-4,88853-34-3,34299-00-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 1 h / 0 °C

1.2: 0.5 h / 0 °C

2.1: acetic acid; water / 0.5 h / 90 °C

3.1: palladium dichloride; methanol / dichloromethane / 24 h / 20 °C / Inert atmosphere

With methanol; water; sodium hydride; acetic acid; palladium dichloride; In dichloromethane; N,N-dimethyl-formamide; mineral oil;

DOI:10.3762/bjoc.12.282

upstream raw materials:

methyl β-L-fucofuranoside

methyl iodide

methyl α-L-fucofuranoside

methyl 3,4-di-O-isopropylidene-α-L-fucopyranoside

Refernces

• 1、 Sommer, Roman,Hauck, Dirk,Varrot, Annabelle,Imberty, Anne,Künzler, Markus,Titz, Alexander. "O-Alkylated heavy atom carbohydrate probes for protein X-ray crystallography: Studies towards the synthesis of methyl 2-O-methyl-L-selenofucopyranoside". supporting information. p. 2828 - 2833. Retrieved 2017/01/09.