Hydrochloric Acid → 2-Carboxyethyl 2,3,4,6-tetra-O-acetyl-1-thio-alpha-D-mannopyranoside

HRID 851673

Reaktionsgleichung

Reaktionsgleichung von HRID 851673
Br.[C:2]([O:5][C@H:6]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:7]1[S:25][C:26](=N)N)(=[O:4])[CH3:3].IC[CH2:31][C:32]([OH:34])=[O:33].C(=O)([O-])[O-].[K+].[K+].S(S([O-])=O)([O-])(=O)=O.[K+].[K+].Cl>CC(C)=O.O.C(Cl)(Cl)Cl>[C:2]([O:5][C@H:6]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:7]1[S:25][CH2:26][CH2:31][C:32]([OH:34])=[O:33])(=[O:4])[CH3:3]

Komponenten

9

Edukt 5

HCID 313Hydrochloric AcidHCID 8856Propanoic acid, 3-iodo-HCID 11430Potassium CarbonateHCID 28019Potassium MetabisulfiteHCID 228232872-S-(2,3,4,6-tetra-O-acetyl-alpha-D-mannopyranosyl)-2-thiopseudourea hydrobromide

Produkt 1

HCID 235244682-Carboxyethyl 2,3,4,6-tetra-O-acetyl-1-thio-alpha-D-mannopyranosideAusbeute 99,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 180AcetoneLösungsmittelHCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A mixture of 2-S-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-2-thiopseudourea hydrobromide (1) (90 g, 0.185 mol), freshly crystallized 3-iodopropionic acid (37 g, 0.199 mol), potassium carbonate (29.6 g, 0.215 mol), and potassium metabisulfite (37 g, 0.167 mol) in acetone (150 ml) and water (150 ml) is stirred for 45 minutes at room temperature. Hydrochloric acid (5%, 700 ml) and chloroform (700 ml) are added to the mixture. The organic layer is separated and washed with water, dried, and evaporated in vacuo to an oil (80 g, quantitative yield) that is used, without further purification, for the preparation of 3.

Aufarbeitung

  1. customThe organic layer is separated
  2. washwashed with water
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f801664b6ce441f7bbdbcc7aa63ecf90
Quelldatensatz
uspto-grants-1983_05
Patentnummer
US04386026

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