Hydrochloric Acid → 2-Carboxyethyl 2,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranoside

HRID 851677

反応式

HRID 851677 の反応式
[C:1]([O:4][C@H:5]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]([CH3:20])[O:8][C@@H:6]1[SH:7])(=[O:3])[CH3:2].I[CH2:22][CH2:23][C:24]([OH:26])=[O:25].C(N(CC)CC)C.Cl>ClCCl>[C:1]([O:4][C@H:5]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]([CH3:20])[O:8][C@@H:6]1[S:7][CH2:22][CH2:23][C:24]([OH:26])=[O:25])(=[O:3])[CH3:2]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 8856Propanoic acid, 3-iodo-HCID 232389082,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranose

生成物 1

HCID 228232862-Carboxyethyl 2,3,4-tri-O-acetyl-1-thio-beta-L-fucopyranoside収率 87%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of 2,3,4-tri-O-acetyl-1-thio-β-L-fucopyranose (1.49 g, 4.87 mmol) and freshly crystallized 3-iodopropionic acid (0.97 g, 4.86 mmol) in dichloromethane (20 ml) containing triethylamine (1.35 ml) is kept for 16 hours at room temperature. Hydrochloric acid (2.5 N, 20 ml) and dichloromethane (10 ml) are added and the solution is washed with water, dried, and evaporated in vacuo to a residue that is put on a column of silica gel and eluted with chloroform-methanol-water, 92.5:7.5:0.75 (v/v/v). Compound 23 is isolated in 87% yield (1.6 g), and used, without further purification, for the preparation of 24.

後処理

  1. washthe solution is washed with water
  2. customdried
  3. customevaporated in vacuo to a residue that
  4. washeluted with chloroform-methanol-water, 92.5:7.5:0.75 (v/v/v)

出典と根拠

ORDレコード
ord-112c947c294a458e9cd332d092afcaeb
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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