4-Toluenesulfonyl chloride → HCID 14010511, compound

HRID 325536Notes

Reaction equation

HRID 325536 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@H:16]([OH:17])[C@@H:15]([CH2:18][O:19][C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[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.[C:39]1([CH3:49])[CH:44]=[CH:43][C:42]([S:45](Cl)(=[O:47])=[O:46])=[CH:41][CH:40]=1>N1C=CC=CC=1>[CH2:1]([O:8][C@@H:9]1[C@H:16]([O:17][S:45]([C:42]2[CH:43]=[CH:44][C:39]([CH3:49])=[CH:40][CH:41]=2)(=[O:47])=[O:46])[C@@H:15]([CH2:18][O:19][C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[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

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 14010509HCID 14010509, compound

Product 1

HCID 14010511HCID 14010511, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Methyl 3-O-benzyl-6-O-trityl-2-deoxy-α-D-ribo-hexopyranoside (13.3 g; 26.05 mmoles) was dissolved in dry pyridine (41 ml) and cooled in an ice bath under nitrogen. p-Toluenesulfonyl chloride (9.93 g, 52.09 mmoles) was added all at once and the reaction was stirred at room temperature under nitrogen overnight. The reaction was partitioned between ether and water. The ether layer was extracted four times with water, dried (K2CO3, anhyd), and the solvent evaporated in veluting with methylene chloride until excess p-toluenesulfonyl chloride had been eluted. Elution was continued with 2% (by volume) acetone in methylene chloride. Fractions containing the product were collected and evaporated to dryness to leave 15.5 g of methyl 3-O-benzyl-4-O-tosyl-6-O-trityl-2-deoxy-α-D-ribo-hexopyranoside as a glassy gum, [α]D25 =66.24 (C, 1.0, CHCL3)

Workup

  1. temperaturecooled in an ice bath under nitrogen
  2. customThe reaction was partitioned between ether and water
  3. extractionThe ether layer was extracted four times with water
  4. dry with materialdried (K2CO3, anhyd)
  5. customthe solvent evaporated in veluting with methylene chloride until excess p-toluenesulfonyl chloride
  6. washhad been eluted
  7. washElution
  8. additionFractions containing the product
  9. customwere collected
  10. customevaporated to dryness

Sources & evidence

ORD record
ord-a2fffbad106543c5a4db59bbded23cde
Source dataset
uspto-grants-1984_04
Patent number
US04440927

Reaction notes

Loading…