1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (3,4,5,6-Tetrahydroxytetrahydropyran-2-ylmethyl)10,12-tricosadiynoate

HRID 865620

반응식

HRID 865620 반응식
CC1(C)[O:10][C@H:9]2[C@H:4]([C@@H:5]([CH2:16][OH:17])[O:6][C@@H:7]3[O:13]C(C)(C)[O:11][C@@H:8]32)[O:3]1.[C:19](O)(=[O:42])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]#[C:29][C:30]#[C:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41].C(N=C=NCCCN(C)C)C>C(Cl)Cl>[C:19]([O:17][CH2:16][CH:5]1[CH:4]([OH:3])[CH:9]([OH:10])[CH:8]([OH:11])[CH:7]([OH:13])[O:6]1)(=[O:42])[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][C:28]#[C:29][C:30]#[C:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]

참가 물질

5

반응물 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 53845710,12-Tricosadiynoic AcidHCID 27236291,2:3,4-Di-O-isopropylidene-alpha-D-galactopyranose

생성물 1

HCID 53883249(3,4,5,6-Tetrahydroxytetrahydropyran-2-ylmethyl)10,12-tricosadiynoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

1,2;3,4-di-O-isopropylidene-D-galactopyranose (2.6 g, 10 mmol) and 10,12-tricosadiynoic acid (3.5 g, 10 mmol) were dissolved in 25 ml methylene chloride. 1-Ethyl-3(3-dimethylaminopropyl)carbodiimide (2 g, >10 mmol) was added neat. The reaction mixture was stirred overnight at room temperature. The reaction mixture was diluted to 100 ml, extracted with water (2×25 ml), dried over MgSO4 and the solvent was removed in vacuo. The crude product was treated with trifluoroacetic acid (10 ml) at room temperature for 30 minutes, evaporated in vacuo, and purified by straight phase chromatography on a CHROMATOTRON, eluted with methanol/chloroform (5:95). The product was characterised by NMR.

후처리

  1. additionThe reaction mixture was diluted to 100 ml
  2. extractionextracted with water (2×25 ml)
  3. dry with materialdried over MgSO4
  4. customthe solvent was removed in vacuo
  5. additionThe crude product was treated with trifluoroacetic acid (10 ml) at room temperature for 30 minutes
  6. customevaporated in vacuo
  7. custompurified by straight phase chromatography on a CHROMATOTRON
  8. washeluted with methanol/chloroform (5:95)

출처 및 근거

ORD 기록
ord-99c35bd0113f409aadcc4e2cb047536f
출처 데이터셋
uspto-grants-1996_10
특허 번호
US05567413

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