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

HRID 2211069Notes

Reaction equation

HRID 2211069 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

Ailyl 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-c6bb80c59a264880ab7a55c164921b68
Source dataset
uspto-grants-1995_10
Patent number
US05461143

Reaction notes

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