Methanesulfonyl chloride → HCID 22803855, Verbindung

HRID 839579Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 839579
[C:1]([S:20][C@@H:21]1[O:29][C@H:28]([CH2:30][OH:31])[C@@H:26]([OH:27])[C@H:24]([OH:25])[C@H:22]1[OH:23])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>N1C=CC=CC=1>[C:1]([S:20][C@@H:21]1[O:29][C@H:28]([CH2:30][O:31][S:33]([CH3:32])(=[O:35])=[O:34])[C@@H:26]([O:27][S:33]([CH3:32])(=[O:35])=[O:34])[C@H:24]([O:25][S:33]([CH3:32])(=[O:35])=[O:34])[C@H:22]1[O:23][S:33]([CH3:32])(=[O:35])=[O:34])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 31297Methanesulfonyl chlorideHCID 54344857HCID 54344857, Verbindung

Produkt 1

HCID 22803855HCID 22803855, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

S-Trityl-1-thio-β-D-glucopyranose (3.6 g.) was dissolved in 50 ml. dry pyridine, cooled to 0° while 5 ml. (7.5 g.) of methylsulfonyl chloride was added. The solution was placed in the refrigerator for 22 hours until thin layer chromatography showed only traces of starting material or partially reacted products remaining. The solvent was removed at reduced pressure. The oily residue was dissolved in chloroform (200 ml.) and was washed with dilute hydrochloric acid and brine. Evaporating the dried organic extract yielded a product which was chromatographed over a silica dry-column using 20% ethyl acetate-80% chloroform eluant. Pure S-trityl-2,3,4,6-tetra-O-methylsulfonyl-1-thio-β-D-glucopyranose was obtained from ether.

Aufarbeitung

  1. customThe solvent was removed at reduced pressure
  2. dissolutionThe oily residue was dissolved in chloroform (200 ml.)
  3. washwas washed with dilute hydrochloric acid and brine
  4. customEvaporating the dried
  5. extractionorganic extract
  6. customyielded a product which
  7. customwas chromatographed over a silica dry-column

Quellen und Nachweise

ORD-Eintrag
ord-ec2e9a4c661b4a40a9c8db8384cfebd9
Quelldatensatz
uspto-grants-1978_06
Patentnummer
US04096250

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