Methanol → methyl L-xylofuranoside

HRID 2253249Notes

Reaction equation

HRID 2253249 reaction equation
[O:1]=[CH:2][C@H:3]([C@@H:5]([C@H:7]([CH2:9][OH:10])[OH:8])[OH:6])[OH:4].[CH3:11]O>Cl>[O:1]([CH3:11])[CH:2]1[O:8][C@@H:7]([CH2:9][OH:10])[C@@H:5]([OH:6])[C@@H:3]1[OH:4]

Participants

4

Reactant 2

HCID 887MethanolHCID 95259L-Xylose

Product 1

HCID 12042993methyl L-xylofuranoside

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

This compound is prepared according to the procedure described in J. Med. Chem. 41: 3865 (1998). L-Xylose is stirred in 0.5N HCl in anhydrous MeOH for 5-10 h at room temperature. The reaction mixture is neutralized with Amberlite IRA-400 OH or Dowex—X200 anion exchange resin. The resin is removed by filtration. The combined filtrate and washings are concentrated to an oil which is subjected to column chromatography on silica gel using a mixture of CH2Cl2 and MeOH as the eluent to afford compound 1-1 as an α/β anomeric mixture.

Workup

  1. customThis compound is prepared
  2. customThe resin is removed by filtration
  3. concentrationThe combined filtrate and washings are concentrated to an oil which
  4. additiona mixture of CH2Cl2 and MeOH as the eluent

Sources & evidence

ORD record
ord-c9ed3a17d0ad461facd648fc1f007edd
Source dataset
uspto-grants-2008_01
Patent number
US07323449B2

Reaction notes

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