α-D-Mannopyranoside, 2-propen-1-yl 2-(acetylamino)-6-azido-2,6-dideoxy-, 3,4-diacetate → HCID 54209402, compound

HRID 962427Notes

Reaction equation

HRID 962427 reaction equation
[C:1]([NH:4][C@H:5]1[C@@H:14]([O:15]C(=O)C)[C@H:13]([O:19]C(=O)C)[C@@H:12]([CH2:23][N:24]=[N+:25]=[N-:26])[O:11][C@@H:6]1[O:7][CH2:8][CH:9]=[CH2:10])(=[O:3])[CH3:2]>CO>[C:1]([NH:4][C@H:5]1[C@@H:14]([OH:15])[C@H:13]([OH:19])[C@@H:12]([CH2:23][N:24]=[N+:25]=[N-:26])[O:11][C@@H:6]1[O:7][CH2:8][CH:9]=[CH2:10])(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 54069077α-D-Mannopyranoside, 2-propen-1-yl 2-(acetylamino)-6-azido-2,6-dideoxy-, 3,4-diacetate

Product 1

HCID 54209402HCID 54209402, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Allyl 2-acetamido-3,4-di-O-acetyl-6-azido-2,6-dideoxy-α-D-mannopyranoside, prepared as described above, (0.5 mg) was dissolved in 10 mL methanol containing 0.2M MeONa. After five minutes, Dowex 50 cation exchange resin was added to the mixture to neutralize. The resin was filtered and the filtrate was concentrated to yield allyl 2-acetamido-6-azido-2,6-dideoxy-α-D-mannopyranoside (99 percent).

Workup

  1. additionDowex 50 cation exchange resin was added to the mixture
  2. filtrationThe resin was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-1e976db8bdf14a6ebf9d1bec3c0fdcac
Source dataset
uspto-grants-1998_06
Patent number
US05759823

Reaction notes

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