Methanol → Methyl D-arabinofuranoside

HRID 858166Notes

Reaction equation

HRID 858166 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 66308D-Arabinose

Product 1

HCID 18637782Methyl D-arabinofuranosideYield 95%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

D-Arabinose (1, 25 g, 167 mmol) was stirred for 5 hours in 0.5% hydrogen chloride in methanol (675 mL) at room temperature and then neutralized with Amberlite IRA-400 OH anion exchange resin. The filtrate and washings were combined and evaporated to dryness and the crude product was purified by silica gel chromatography (CHCl3/MeOH, 92:8) to afford 26.2 g of methyl D-arabinofuranoside (2, 95% yield) as an and (1:1) mixture. MS 164 (M)+.

Workup

  1. customevaporated to dryness
  2. customthe crude product was purified by silica gel chromatography (CHCl3/MeOH, 92:8)

Sources & evidence

ORD record
ord-7e666b16ceb8413fb376c4980a514b8d
Source dataset
uspto-grants-2006_12
Patent number
US07148223B2

Reaction notes

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