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

HRID 865620

Reaktionsgleichung

Reaktionsgleichung von HRID 865620
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]

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-99c35bd0113f409aadcc4e2cb047536f
Quelldatensatz
uspto-grants-1996_10
Patentnummer
US05567413

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