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

HRID 564900Notes

Reaction equation

HRID 564900 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 0.2 M 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. additionAfter five minutes Dowex 50 cation exchange resin was added to the mixture
  2. filtrationThe resin was filtered
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-b630bf53372844fa985f7595b4a00b30
Source dataset
uspto-grants-2001_01
Patent number
US06168934A

Reaction notes

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