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

HRID 2086379Notes

Reaction equation

HRID 2086379 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. customdried over MgSo4
  2. customevaporated
  3. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-285d501f80df47c3a444df0d3fdfe53f
Source dataset
uspto-grants-2004_04
Patent number
US06723843B2

Reaction notes

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