Chloroform → 2,3,4-Tri-O-acetyl-6-deoxy-6-phthalimido-1-thio-beta-D-galactopyranose

HRID 1155299

Reaction equation

HRID 1155299 reaction equation
C(Cl)(Cl)Cl.[C:5]([O:8][C@@H:9]1[C@@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@@H:13]([O:19][C:20](=[O:22])[CH3:21])[C@@H:12]([CH2:23][N:24]2[C:28](=[O:29])[C:27]3=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]3[C:25]2=[O:34])[O:11][C@H:10]1[S:35]C(=N)N)(=[O:7])[CH3:6].S(S([O-])=O)([O-])(=O)=O.[K+].[K+]>O>[C:5]([O:8][C@@H:9]1[C@@H:14]([O:15][C:16](=[O:18])[CH3:17])[C@@H:13]([O:19][C:20](=[O:22])[CH3:21])[C@@H:12]([CH2:23][N:24]2[C:28](=[O:29])[C:27]3=[CH:30][CH:31]=[CH:32][CH:33]=[C:26]3[C:25]2=[O:34])[O:11][C@H:10]1[SH:35])(=[O:7])[CH3:6]

Participants

5

Reactant 3

HCID 6212ChloroformHCID 28019Potassium MetabisulfiteHCID 228184952-S-(2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-beta-D-galactopyranosyl)-2-thiopseudourea

Product 1

HCID 128055222,3,4-Tri-O-acetyl-6-deoxy-6-phthalimido-1-thio-beta-D-galactopyranoseYield 80.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Chloroform (9.0 ml.) is added to a solution of 2-S-(2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-β-D-galactopyranosyl)-2-thiopseudourea (3.4 g.) in water (10 ml.) containing potassium metabisulfite (1.38 g.). The mixture is heated with stirring under reflux for 15 minutes. The cooled solution is separated, and the organic layer is dried and evaporated in vacuo to give the title compound (2.5 g.). This material is used directly for the preparation of 6-(5-cholesten-3β-yloxy)hexyl 2,3,4-tri-O-acetyl-6-deoxy-6-phthalimido-1-thio-β-D-galactopyranoside.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 15 minutes
  3. customThe cooled solution is separated
  4. customthe organic layer is dried
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-abb92f3266ad4ce1aadfc5fd46956688
Source dataset
uspto-grants-1981_11
Patent number
US04301152

Linked notes

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