Acetic Acid → HCID 91272540, compound

HRID 967341Notes

Reaction equation

HRID 967341 reaction equation
[N:1]([C@@H:4]1[C@@H:11]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C@H:10]([O:22][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C@@H:9]([CH2:30][O:31][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[O:8][C@H:5]1[S:6][CH3:7])=[N+:2]=[N-:3].CC(O)=O>CCOC(C)=O>[N:1]([C@@H:4]1[C@@H:11]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=2)[C@H:10]([O:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C@@H:9]([CH2:30][OH:31])[O:8][C@H:5]1[S:6][CH3:7])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 23396148HCID 23396148, compoundHCID 178435178HCID 178435178, compound

Product 1

HCID 91272540HCID 91272540, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of methyl 2-azido-4-O-benzyl-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (32) (1.5 g, 2.2 mmol) and anhydrous AcOH (28.8 mL) in dry THF (169 mL) hydrogen fluoride-pyridine complex (20.3 mL) was added in a polypropylene container. The reaction mixture was kept at room temperature overnight, then diluted with EtOAc (1 L). The resulting solution was washed with saturated sodium hydrogen carbonate (4×1 L), saturated brine solution (1 L), dried over MgSO4 and evaporated to dryness. The residue was crystallized from MeOH. The mother liquor was evaporated, the residue was treated with hexane to get more solid. The solid products were combined affording methyl 2-azido-4-O-benzyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (33) (735 mg, 75%).

Workup

  1. washThe resulting solution was washed with saturated sodium hydrogen carbonate (4×1 L), saturated brine solution (1 L)
  2. dry with materialdried over MgSO4
  3. customevaporated to dryness
  4. customThe residue was crystallized from MeOH
  5. customThe mother liquor was evaporated
  6. additionthe residue was treated with hexane
  7. customto get more solid

Sources & evidence

ORD record
ord-7ec0fb8768d14427aefa7ae19e35afc0
Source dataset
uspto-grants-2005_10
Patent number
US06953850B1

Reaction notes

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