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

HRID 233554Notes

Reaction equation

HRID 233554 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-793803cf6d6b4240bf97ec23fbe9732d
Source dataset
uspto-grants-1997_01
Patent number
US05593887

Reaction notes

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