Pyridine → HCID 12114363, compound

HRID 967338Notes

Reaction equation

HRID 967338 reaction equation
C([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Si:11]([C:43]1[CH:48]=CC=C[CH:44]=1)([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[O:12][CH2:13][C@H:14]1[O:21][C@@H:18]([S:19][CH3:20])[C@H:17]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)[C@@H:16]([O:32][CH2:33][CH:34]=[CH2:35])[C@H:15]1[OH:36])(C)(C)C.[C:49](OC(=O)C)(=[O:51])[CH3:50].N1C=CC=C[CH:57]=1>>[Si:11]([O:12][CH2:13][C@H:14]1[O:21][C@@H:18]([S:19][CH3:20])[C@H:17]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][C:27]([O:30][CH3:31])=[CH:28][CH:29]=2)[C@@H:16]([O:32][CH2:33][CH:34]=[CH2:35])[C@H:15]1[O:36][C:49](=[O:51])[CH3:50])([C:43]([CH3:44])([CH3:57])[CH3:48])([C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:6]1[CH:5]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 131725189HCID 131725189, compound

Product 1

HCID 12114363HCID 12114363, compoundYield 48%

Procedure

To a solution of methyl 6-O-(t-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-3-O-allyl-1-thio-β-D-galactopyranosidee (30) (1.4 g, 2.3 mmol) in pyridine (30 mL) was added acetic anhydride (20 g, 196 mmol) in one portion. The resulting solution was left to stir at room temperature for 72 h. The reaction contents were then evaporated to dryness and there residue was dissolved in dichloromethane (200 mL). The solution was washed with potassium hydrogen sulphate solution (1 M×2×50 mL) followed by saturated sodium chloride (150 mL), dried over MgSO4 and evaporated to dryness. The crude residue was purified by chromatography using dichloromethane as the mobile phase to give Methyl 6-O-(t-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-3-O-allyl-4-O-acetyl-1-thio-β-D-galactopyranoside (31)(750 mg, 48%) as a pale yellow oil.

Workup

  1. waitThe resulting solution was left
  2. customThe reaction contents
  3. customwere then evaporated to dryness and there residue
  4. dissolutionwas dissolved in dichloromethane (200 mL)
  5. washThe solution was washed with potassium hydrogen sulphate solution (1 M×2×50 mL)
  6. dry with materialdried over MgSO4
  7. customevaporated to dryness
  8. customThe crude residue was purified by chromatography

Sources & evidence

ORD record
ord-dc9b3cb88b054476b4da9c7bea64d24a
Source dataset
uspto-grants-2005_10
Patent number
US06953850B1

Reaction notes

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