Triethylamine → 6-(5-Cholesten-3beta-yloxy)hexyl 2,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranoside

HRID 1105878ノート

反応式

HRID 1105878 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]([CH3:20])[O:8][C@@H:6]1[SH:7])(=[O:3])[CH3:2].[CH3:21][CH:22]([CH2:24][CH2:25][CH2:26][C@H:27]([C@@H:29]1[C@:46]2([CH3:47])[C@H:32]([C@H:33]3[C@H:43]([CH2:44][CH2:45]2)[C@:41]2([CH3:42])[C:36]([CH2:37][C@@H:38]([O:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54]I)[CH2:39][CH2:40]2)=[CH:35][CH2:34]3)[CH2:31][CH2:30]1)[CH3:28])[CH3:23].C(N(CC)CC)C>ClCCl>[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]([CH3:20])[O:8][C@@H:6]1[S:7][CH2:54][CH2:53][CH2:52][CH2:51][CH2:50][CH2:49][O:48][C@H:38]1[CH2:39][CH2:40][C@@:41]2([CH3:42])[C:36](=[CH:35][CH2:34][C@@H:33]3[C@@H:43]2[CH2:44][CH2:45][C@@:46]2([CH3:47])[C@H:32]3[CH2:31][CH2:30][C@@H:29]2[C@H:27]([CH3:28])[CH2:26][CH2:25][CH2:24][CH:22]([CH3:23])[CH3:21])[CH2:37]1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 128055256-(5-Cholesten-3beta-yloxy)hexyl iodideHCID 232389082,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranose

生成物 1

HCID 1317126436-(5-Cholesten-3beta-yloxy)hexyl 2,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranoside収率 61%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2,3,4-Tri-O-acetyl-1-thio-β-L-fucopyranose (10 mmol) is treated with 6-(5-cholesten-3β-yloxy)hexyl iodide (10 mmol) in dichloromethane (30 ml) containing triethylamine (10 mmol). The reaction takes place in 1 day at room temperature under nitrogen. The resulting solution is washed with distilled water (20 ml) and dried with anhydrous sodium sulfate. The filtered solution is concentrated to form a syrup which is put on a silica gel column and eluted with chloroform followed by 1.0% ethanol in chloroform. The fractions containing the title compound, as determined by thin layer chromatography, are pooled and evaporated to give the title compound in 61% yield [α]D -4° (c 1.5, chloroform).

後処理

  1. customin 1 day
  2. customat room temperature
  3. washThe resulting solution is washed with distilled water (20 ml)
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationThe filtered solution is concentrated
  6. customto form a syrup which
  7. washeluted with chloroform
  8. additionThe fractions containing the title compound
  9. customevaporated

出典と根拠

ORDレコード
ord-11d0510d869e4df58af621773eb555f4
出典データセット
uspto-grants-1982_01
特許番号
US04310505

反応ノート

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