Dimethyl Sulfoxide → HCID 70436310, compound

HRID 325539Notes

Reaction equation

HRID 325539 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@H:16](OS(C2C=CC(C)=CC=2)(=O)=O)[C@@H:15]([CH2:28][OH:29])[O:14][C@H:11]([O:12][CH3:13])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(C)=O.[BH4-].[Na+]>CCOCC>[CH2:1]([O:8][C@@H:9]1[CH2:16][C@@H:15]([CH2:28][OH:29])[O:14][C@H:11]([O:12][CH3:13])[CH2:10]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 4311764Sodium borohydrideHCID 13317003HCID 13317003, compound

Product 1

HCID 70436310HCID 70436310, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
80 °C

Procedure

Methyl 3-O-benzyl-4-O-tosyl-2-deoxy-α-D-ribo-hexopyranoside (6.55 g, 15.50 mmoldry DMSO (50 ml). Sodium borohydride (2.35 g; 62.01 mmoles) is added and the reaction is stirred under nitrogen in a bath maintained at 80° C. for four days. The reaction is cooled to room temperature and diluted with ether and extracted with water. The aqueous extract is then extracted four times with ether. The combined ether extracts are dried (MgSO4), filtered, and the solvent evaporated in vacuo to give crude product. This crude product is purified by flash chromatography on a 60 mm×150 mm column eluting with 15% (by volume) acetone in methylene chloride. A small portion (0.9 g) containing an impurity is rechromatographed on a 30 mm×130 mm column with the same eluant to give a combined total of 3.18 g of methyl 3-O-benzyl-2,4-dideoxy-α-D-erythro-hexopyranoside as a gum, [α]D25 +58.56 (c, 0.7, CHCl3)

Workup

  1. temperatureThe reaction is cooled to room temperature
  2. extractionextracted with water
  3. extractionThe aqueous extract
  4. extractionis then extracted four times with ether
  5. dry with materialThe combined ether extracts are dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. customto give crude product
  9. customThis crude product is purified by flash chromatography on a 60 mm×150 mm column
  10. washeluting with 15% (by volume) acetone in methylene chloride
  11. additionA small portion (0.9 g) containing an impurity
  12. customis rechromatographed on a 30 mm×130 mm column with the same eluant

Sources & evidence

ORD record
ord-a5c2564a5e4d4e6bbb57fd763651c748
Source dataset
uspto-grants-1984_04
Patent number
US04440927

Reaction notes

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