Trityl chloride → HCID 13633137, Verbindung

HRID 1703948Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1703948
[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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 13633137HCID 13633137, VerbindungAusbeute 29,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

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°.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-634413bee17542baa4e6a7c0f3a15ec9
Quelldatensatz
uspto-grants-1978_11
Patentnummer
US04125710

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