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

HRID 564899Notes

Reaction equation

HRID 564899 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-4a8322ccb9b647ca93d2ed5d43d96ba6
Source dataset
uspto-grants-2001_01
Patent number
US06168934A

Reaction notes

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