Trityl chloride → HCID 13633137、化合物

HRID 1703948ノート

反応式

HRID 1703948 の反応式
[C:1]([O:4][C@@H:5]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[O:8][C@H:6]1[SH:7])(=[O:3])[CH3:2].[C:25]1([C:31](Cl)([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1>N1C=CC=CC=1>[C:1]([O:4][C@@H:5]1[C@@H:11]([O:12][C:13](=[O:15])[CH3:14])[C@H:10]([O:16][C:17](=[O:19])[CH3:18])[C@@H:9]([CH2:20][O:21][C:22](=[O:24])[CH3:23])[O:8][C@H:6]1[S:7][C:31]([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)([C:38]1[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)(=[O:3])[CH3:2]

参加物

4

反応物 2

HCID 6456Trityl chlorideHCID 88293beta-D-Glucopyranose, 1-thio-, 2,3,4,6-tetraacetate

生成物 1

HCID 13633137HCID 13633137、化合物収率 29.2%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

A pyridine solution (100 ml) of 35 g (0.096 mole) of 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranose [Methods in Carbohydrate Chemistry, Vol. 2, 436 (1963)] and 28 g (0.10 mole) of triphenylmethyl chloride was stirred at room temperature for 12 hours. The solution was filtered and the pyridine removed at reduced pressure. The residue was dissolved in chloroform (350 ml), washed with water (5 × 100 ml) and the chloroform solution dried in magnesium sulfate. The solvent was removed at reduced pressure and the residue dissolved in methanol and cooled to give 17 g (29%) of crystalline 2,3,4,6-tetra-O-acetyl-1-S-trityl-1-thio-β-D-glucopyranose, m.p. 177°-179°; [α]D25 (1% methanol) = -37.8°.

後処理

  1. filtrationThe solution was filtered
  2. customthe pyridine removed at reduced pressure
  3. dissolutionThe residue was dissolved in chloroform (350 ml)
  4. washwashed with water (5 × 100 ml)
  5. dry with materialthe chloroform solution dried in magnesium sulfate
  6. customThe solvent was removed at reduced pressure
  7. dissolutionthe residue dissolved in methanol
  8. temperaturecooled

出典と根拠

ORDレコード
ord-634413bee17542baa4e6a7c0f3a15ec9
出典データセット
uspto-grants-1978_11
特許番号
US04125710

反応ノート

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