Ethanethiol → HCID 131723781, compound

HRID 1859413Notes

Reaction equation

HRID 1859413 reaction equation
C(O[C@@H:5]1[O:20][C@@H:19]([CH2:21][O:22][C:23](=[O:25])[CH3:24])[C@@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@H:11]([O:12][CH3:13])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=O)C.C([SH:28])C.B(F)(F)F.CCO[CH2:36][CH3:37].C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[CH2:36]([C@:5]1([O:20][C@@H:19]([CH2:21][O:22][C:23](=[O:25])[CH3:24])[C@@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@H:11]([O:12][CH3:13])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])[SH:28])[CH3:37]

Participants

7

Reactant 4

HCID 6343EthanethiolHCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 57261560HCID 57261560, compound

Product 1

HCID 131723781HCID 131723781, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

1,2,4,6-Tetra-O-acetyl-3-O-methyl-α-L-idopyranose (prepared as described for its per-benzoyl analogue by replacing benzoyl chloride with acetic anhydride; Jaurand et al. Bio. Med. Chem. Lett, 1992, 2, 897-900) (48.4 g) is dissolved in toluene (175 ml). Ethanethiol (20 ml) and boron trifluoride etherate (1M in toluene, 134 ml) are added under a nitrogen atmosphere. After stirring for 1 hour, aqueous sodium hydrogen carbonate (400 ml) and the mixture is added and the mixture is stirred for 1 hour. The mixture is then poured into ethyl acetate. The organic phase is washed twice with water and concentrated. Purification by chromatography on a column of silica gel gives 29.6 g of compound 52.

Workup

  1. stirringthe mixture is stirred for 1 hour
  2. washThe organic phase is washed twice with water
  3. concentrationconcentrated
  4. customPurification by chromatography on a column of silica gel

Sources & evidence

ORD record
ord-779162658f9e4a348e58be2b57e74644
Source dataset
uspto-grants-2003_03
Patent number
US06528497B1

Reaction notes

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