Sodium Iodide → allyl 2-acetamido-3,4-di-O-acetyl-2,6-dideoxy-6-iodo-alpha-D-mannopyranoside

HRID 2211068Notes

Reaction equation

HRID 2211068 reaction equation
[C:1]([NH:4][C@H:5]1[C@@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@H:13]([O:19][C:20](=[O:22])[CH3:21])[C@@H:12]([CH2:23]OS(C2C=CC=CC=2C)(=O)=O)[O:11][C@@H:6]1[O:7][CH2:8][CH:9]=[CH2:10])(=[O:3])[CH3:2].[Na+].[I-:36]>>[C:1]([NH:4][C@H:5]1[C@@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@H:13]([O:19][C:20](=[O:22])[CH3:21])[C@@H:12]([CH2:23][I:36])[O:11][C@@H:6]1[O:7][CH2:8][CH:9]=[CH2:10])(=[O:3])[CH3:2]

Participants

3

Reactant 2

HCID 5238Sodium IodideHCID 86749068allyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-tolylsulfonyl-alpha-D-mannopyranoside

Product 1

HCID 15663094allyl 2-acetamido-3,4-di-O-acetyl-2,6-dideoxy-6-iodo-alpha-D-mannopyranosideYield 88%

Procedure

A solution of allyl 2-acetamido-3,4-di-O-acetyl-2-deoxy-6-O-tolylsulfonyl-α-D-mannopyranoside, prepared as described above, (3.68 g, 7.37 mmol) and NaI (2.21 g, 14.7 mmol) was gently refluxed for 10 hours, and cooled. The mixture was concentrated, and the residue was chromatographed on silica gel, with toluene-EtOAc (1:2), to give allyl 2-acetamido-3,4-di-O-acetyl-2,6-dideoxy-6-iodo-α-D-mannopyranoside (2.96 g, 88 percent);

Workup

  1. temperaturecooled
  2. concentrationThe mixture was concentrated
  3. customthe residue was chromatographed on silica gel, with toluene-EtOAc (1:2)

Sources & evidence

ORD record
ord-0ca0ba47c6df49e3b2c8ccc8e01d3529
Source dataset
uspto-grants-1995_10
Patent number
US05461143

Reaction notes

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