Water → HCID 15699537, compound

HRID 1706841Notes

Reaction equation

HRID 1706841 reaction equation
[O:1]([CH3:11])[C@H:2]1[O:8][C@H:7]([CH2:9][OH:10])[C@@H:5]([OH:6])[CH2:4][CH2:3]1.[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1.[OH2:23]>N1C=CC=CC=1>[C:12]1([CH3:22])[CH:17]=[CH:16][C:15]([S:18]([O:6][C@@H:5]2[C@@H:7]([CH2:9][O:10][S:18]([C:15]3[CH:16]=[CH:17][C:12]([CH3:22])=[CH:13][CH:14]=3)(=[O:19])=[O:23])[O:8][C@H:2]([O:1][CH3:11])[CH2:3][CH2:4]2)(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 13379420HCID 13379420, compound

Product 1

HCID 15699537HCID 15699537, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl 2,3-dideoxy-α-D-erythro-hexopyranoside (6 g, 37 mmol) in dry pyridine (50 ml) was treated with toluene-p-sulphonyl chloride (15.2 g, 80 mmol) at 0° with stirring. The reaction mixture was stored at 22° for 12 h, and after the addition of water (1 ml) it was concentrated. The syrupy residue was poured into ice-water, the oil which separated was extracted with CHCl3, and the extracts were washed with water, dried and evaporated. The solid thus obtained (12 g, 70%) was recrystallized from methanol to give pure methyl 2,3-dideoxy-4,6-di-O-toluene-p-sulphonyl-α-D-erythro-hexopyranoside. M.p.: 110°-111.5°. [α]D22 +80.8° (c 1, chloroform).

Workup

  1. concentrationwas concentrated
  2. additionThe syrupy residue was poured into ice-water
  3. customthe oil which separated
  4. extractionwas extracted with CHCl3
  5. washthe extracts were washed with water
  6. customdried
  7. customevaporated
  8. customThe solid thus obtained (12 g, 70%)
  9. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-baa6b0984a76467387e45475f6548abb
Source dataset
uspto-grants-1980_06
Patent number
US04208531

Reaction notes

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