4-Toluenesulfonyl chloride → HCID 14010511, compound

HRID 1719623Notes

Reaction equation

HRID 1719623 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 vacuo to leave 19.1 g of crude product which was chromatographed on silica gel (1 kg) eluting 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 vacuo
  6. customto leave 19.1 g of crude product which
  7. customwas chromatographed on silica gel (1 kg)
  8. washeluting with methylene chloride until excess p-toluenesulfonyl chloride
  9. washhad been eluted
  10. washElution
  11. additionFractions containing the product
  12. customwere collected
  13. customevaporated to dryness

Sources & evidence

ORD record
ord-5b8db3a10cdc48cb957bf47851536194
Source dataset
uspto-grants-1985_09
Patent number
US04540796

Reaction notes

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