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

HRID 851673

反応式

HRID 851673 の反応式
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]

参加物

9

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 180Acetone溶媒HCID 962Water溶媒HCID 6212Chloroform溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-f801664b6ce441f7bbdbcc7aa63ecf90
出典データセット
uspto-grants-1983_05
特許番号
US04386026

関連ノート

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