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

HRID 1105878

Reaction equation

HRID 1105878 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-11d0510d869e4df58af621773eb555f4
Source dataset
uspto-grants-1982_01
Patent number
US04310505

Linked notes

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