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 991155ノート

反応式

HRID 991155 の反応式
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]

参加物

5

反応物 3

HCID 24287Tin tetrachlorideHCID 78378AzidotrimethylsilaneHCID 2802067Lactose octaacetate

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-f2796038b5264caea933d86126f27f55
出典データセット
uspto-grants-2002_10
特許番号
US06462183B1

反応ノート

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