Tin tetrachloride → beta-D-Galactopyranosyl azide, 2,3,4,6-tetraacetate

HRID 1368567Notes

Reaction equation

HRID 1368567 reaction equation
C(O[CH:5]1[O:22][C@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[C@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:6]1[O:7][C:8](=[O:10])[CH3:9])(=O)C.C[Si]([N:32]=[N+:33]=[N-:34])(C)C.Cl[Sn](Cl)(Cl)Cl>C(Cl)Cl>[C:8]([O:7][C@@H:6]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@@H:16]([O:17][C:18](=[O:20])[CH3:19])[C@@H:21]([CH2:23][O:24][C:25](=[O:27])[CH3:26])[O:22][C@H:5]1[N:32]=[N+:33]=[N-:34])(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 78378AzidotrimethylsilaneHCID 2729838((2R,3S,4S,5R)-3,4,5,6-tetrakis(acetyloxy)oxan-2-yl)methyl acetate

Product 1

HCID 2781041beta-D-Galactopyranosyl azide, 2,3,4,6-tetraacetateYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1,2,3,4,6-penta-O-acetyl-galactopyranose (1.17 g, 3 mmol) was dissolved in dry CH2Cl2 (15 ml), then trimethylsilyl azide (416 mg, 3.6 mmol) and SnCl4 (0.18 ml) were added under nitrogen. The mixture was stirred at room temperature for 24 hours. The reaction mixture was subsequently diluted with CH2Cl2 (40 ml), dried over MgSO4 and evaporated. The residue was purified by chromatography using hexane/EtOAc 8:7 v/v as the mobile phase to give 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl azide (1.05 g, 94%).

Workup

  1. dry with materialdried over MgSO4
  2. customevaporated
  3. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-066da538f0be443daa6ce52dc1be467c
Source dataset
uspto-grants-2003_06
Patent number
US06573337B1

Reaction notes

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