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 991155노트

반응식

HRID 991155 반응식
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]

참가 물질

5

반응물 3

HCID 24287Tin tetrachlorideHCID 78378AzidotrimethylsilaneHCID 2802067Lactose octaacetate

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-f2796038b5264caea933d86126f27f55
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06462183B1

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