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ChemicalBook CAS DataBase List METHYL ALPHA-L-RHAMNOPYRANOSIDE
14917-55-6

METHYL ALPHA-L-RHAMNOPYRANOSIDE synthesis

13synthesis methods
-

Yield:-

Reaction Conditions:

in methanol

Steps:

Preparative synthesis of the acceptor reaction product (cf.
Figure 2C) Methyl α-L-rhamnopyranoside (ref. 78): To a solution of 5 g (27.4 mmol) of L-Rhamnose monohydrate in 50 mL of MeOH was added 5g of Dowex X8-200 ion exchange resin (H+). The reaction mixture was refluxed for 24h, cooled to room temperature, and filtered. The residue was purified by flash chromatography on silica gel (DCM/MeOH, 88/12) to give 4.4 g of known methyl α-L-rhamnopyranoside as a yellow syrup (90%) as the first eluding product, and 400 mg of methyl β-L-rhamnopyranoside (8%) as the second eluding one.

References:

Institut Pasteur EP2100966, 2009, A1

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