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

HRID 851677

반응식

HRID 851677 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-112c947c294a458e9cd332d092afcaeb
출처 데이터셋
uspto-grants-1983_05
특허 번호
US04386026

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