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

HRID 851673

반응식

HRID 851673 반응식
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]

참가 물질

9

반응물 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

생성물 1

HCID 235244682-Carboxyethyl 2,3,4,6-tetra-O-acetyl-1-thio-alpha-D-mannopyranoside수율 99.1%

시약·촉매·용매 3

HCID 180Acetone용매HCID 962Water용매HCID 6212Chloroform용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-f801664b6ce441f7bbdbcc7aa63ecf90
출처 데이터셋
uspto-grants-1983_05
특허 번호
US04386026

연결된 노트

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