Methanol → HCID 67923335, compound

HRID 2050668Notes

Reaction equation

HRID 2050668 reaction equation
[CH2:1]([O:8][C@H:9]1[C@@H:15]([CH2:16][C:17]#[N:18])[O:14][CH:11]([O:12][CH3:13])[C@@H:10]1OS(C(F)(F)F)(=O)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.B.CSC.CO>C1CCCCC1>[CH2:1]([O:8][C@H:9]1[C@H:15]2[CH2:16][CH2:17][NH:18][C@@H:10]1[CH:11]([O:14]2)[O:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 12423031(Dimethyl sulfide)trihydroboronHCID 18645159HCID 18645159, compound

Product 1

HCID 67923335HCID 67923335, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A 1:2 mixture of the α and β anomers of methyl 3-O-benzyl-5-cyano-5-deoxy-2-O-trifluoromethanesulphonyl-D-xylofuranoside (21αβ) (2.51 g, 6.36 mmol) dissolved in cyclohexane (200 ml) at 40° C. was treated with borane-dimethyl sulphide complex (10M in THF, 955 μl, 9.55 mmol) then stirred at room temperature overnight. Methanol (1 ml) was added, and the solvents evaporated then replaced with a 1:1 mixture of methanol and pyridine (50 ml). This was stirred with potassium carbonate (5 g) at room temperature for 48 hours. The solvents were removed and the residue dissolved in dichloromethane (20 ml), filtered and concentrated by evaporation. Purification using flash chromatography produced methyl 3-O-benzyl-2,6-imino-2,5,6-trideoxy-D-lyxohexofuranoside (α:β 1:2) (1.52 g, 96%) as a partially separated mixture of colourless oils which rapidly turn brown on storage.

Workup

  1. customthe solvents evaporated
  2. additionthen replaced with a 1:1 mixture of methanol and pyridine (50 ml)
  3. stirringThis was stirred with potassium carbonate (5 g) at room temperature for 48 hours
  4. customThe solvents were removed
  5. dissolutionthe residue dissolved in dichloromethane (20 ml)
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. customPurification

Sources & evidence

ORD record
ord-26703bcf84f34065a9a3b83a4e71337e
Source dataset
uspto-grants-1991_05
Patent number
US05013842

Reaction notes

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