HCID 23396150, compound → HCID 91159024, compound

HRID 967345Notes

Reaction equation

HRID 967345 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][C:23]([C:25]2[C:26]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:24])[C@@H:9]([CH2:37][O:38][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>[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][C:23]([C:25]2[C:26]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)=[CH:27][CH:28]=[CH:29][CH:30]=2)=[O:24])[C@@H:9]([CH2:37][OH:38])[O:8][C@H:5]1[S:6][CH3:7])=[N+:2]=[N-:3]

Participants

4

Reactant 2

HCID 23396150HCID 23396150, compoundHCID 178435178HCID 178435178, compound

Product 1

HCID 91159024HCID 91159024, compoundYield 94.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of methyl 2-azido-4-O-biphenylcarbonyl-6-O-tert-butyldiphenylsilyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (11) (150 mg, 0.19 mmol) and anhydrous AcOH (2.8 mL) in dry THF (17 mL) hydrogenfluoride-pyridine complex (2 mL) was added in a polypropylene container. The reaction mixture was kept at room temperature overnight, then diluted with EtOAC (100 mL). The resulting solution was washed with saturated sodiumhydrogen carbonate (4×100 mL), saturated brine solution (100 mL), dried over MgSO4 and evaporated to dryness. The residue was purified by chromatography using EtOAC—hexane 2:5 as the mobile phase to give methyl 2-azido-4-O-biphenylcarbonyl-2-deoxy-3-O-(4-methoxybenzyl)-1-thio-β-D-glucopyranoside (40) (96 mg, 93%).

Workup

  1. additiondiluted with EtOAC (100 mL)
  2. washThe resulting solution was washed with saturated sodiumhydrogen carbonate (4×100 mL), saturated brine solution (100 mL)
  3. dry with materialdried over MgSO4
  4. customevaporated to dryness
  5. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-a77b2c05b725494d961c7c4d857bd748
Source dataset
uspto-grants-2005_10
Patent number
US06953850B1

Reaction notes

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