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

HRID 1871831

Reaktionsgleichung

Reaktionsgleichung von HRID 1871831
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 remove din 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 remove din 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-246a4881265c4d1ab7a1cae9220fb625
Quelldatensatz
uspto-grants-2000_08
Patentnummer
US06106806

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