Tin tetrachloride → 4-O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)-2,3,6-tri-O-acetyl-beta-D-glucopyranosyl azide

HRID 991155Notes

Reaction equation

HRID 991155 reaction equation
C(O[C@@H:5]1[O:42][C@H:41]([CH2:43][O:44][C:45](=[O:47])[CH3:46])[C@@H:16]([O:17][C@@H:18]2[O:35][C@H:34]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[C@H:29]([O:30][C:31](=[O:33])[CH3:32])[C@H:24]([O:25][C:26](=[O:28])[CH3:27])[C@H:19]2[O:20][C:21](=[O:23])[CH3:22])[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:52]=[N+:53]=[N-:54])(C)C.Cl[Sn](Cl)(Cl)Cl>C(Cl)Cl>[C:21]([O:20][C@@H:19]1[C@@H:24]([O:25][C:26](=[O:28])[CH3:27])[C@@H:29]([O:30][C:31](=[O:33])[CH3:32])[C@@H:34]([CH2:36][O:37][C:38](=[O:40])[CH3:39])[O:35][C@@H:18]1[O:17][C@@H:16]1[C@@H:41]([CH2:43][O:44][C:45](=[O:47])[CH3:46])[O:42][C@@H:5]([N:52]=[N+:53]=[N-:54])[C@H:6]([O:7][C:8](=[O:10])[CH3:9])[C@H:11]1[O:12][C:13](=[O:15])[CH3:14])(=[O:23])[CH3:22]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 78378AzidotrimethylsilaneHCID 2802067Lactose octaacetate

Product 1

HCID 233928434-O-(2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranosyl)-2,3,6-tri-O-acetyl-beta-D-glucopyranosyl azideYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of β-lactose octaacetate (203 mg, 0.3 mmol), trimethylsilyl azide (41 mg, 0.35 mmol), and SnCl4 (40 mg, 0.15 mmol) in CH2Cl2 (1.5 ml) was stirred overnight at room temperature. The solution was diluted with CH2Cl2 (20 ml) and washed twice with 1 M potassium fluoride solution (5 ml), water (5 ml) and evaporated affording 4-O-(2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl)-2,3,6-tri-O-acetyl-β-D-glucopyranosyl azide (25) (178 mg 90%).

Workup

  1. washwashed twice with 1 M potassium fluoride solution (5 ml), water (5 ml)
  2. customevaporated

Sources & evidence

ORD record
ord-f2796038b5264caea933d86126f27f55
Source dataset
uspto-grants-2002_10
Patent number
US06462183B1

Reaction notes

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