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

HRID 1155299

반응식

HRID 1155299 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-abb92f3266ad4ce1aadfc5fd46956688
출처 데이터셋
uspto-grants-1981_11
특허 번호
US04301152

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