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

HRID 233555Notes

Reaction equation

HRID 233555 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 rag) 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-f9e92ba05efe49878e6a35c26bccdfd6
Source dataset
uspto-grants-1997_01
Patent number
US05593887

Reaction notes

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