7-Dehydrocholesterol → Previtamin D3

HRID 1077380

Reaktionsgleichung

Reaktionsgleichung von HRID 1077380
[CH3:1][C@@H:2]([C@@H:9]1[C@@:13]2([CH3:28])[CH2:14][CH2:15][C@@H:16]3[C@@:21]4([CH3:27])[CH2:22][CH2:23][C@H:24]([OH:26])[CH2:25][C:20]4=[CH:19][CH:18]=[C:17]3[C@@H:12]2[CH2:11][CH2:10]1)[CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7]>CCCCCC>[CH3:27][C:21]1[CH2:22][CH2:23][C@H:24]([OH:26])[CH2:25][C:20]=1/[CH:19]=[CH:18]\[C:17]1[C@@H:12]2[CH2:11][CH2:10][C@H:9]([C@@H:2]([CH2:3][CH2:4][CH2:5][CH:6]([CH3:8])[CH3:7])[CH3:1])[C@@:13]2([CH3:28])[CH2:14][CH2:15][CH:16]=1

Komponenten

3

Edukt 1

HCID 4394237-Dehydrocholesterol

Produkt 1

HCID 5281058Previtamin D3

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058HexaneLösungsmittel

Versuchsvorschrift

From the hexane data, it was concluded that the material eluted at 12.2 min is tachysterol. The size and kind of microreactor is important to the ratio of products formed. Where the microreactor is several times the size of the 7-DHC, the undesirable side reactions are more favored. For example the silica with 60 Å pores (Ex. 10 and 11) give a ratio of previtamin D3 :tachysterol similar to that of the reaction in hexane (Ex. 9). In micelles (Ex. 16), however, which form a similarly sized microreactor, but with an environment similar to that of a hydrocarbon solvent, tachysterol is very heavily favored.

Aufarbeitung

  1. washeluted at 12.2 min
  2. customformed

Quellen und Nachweise

ORD-Eintrag
ord-f6bb1851d396499fbfe04619d81b2ea2
Quelldatensatz
uspto-grants-1996_08
Patentnummer
US05543016

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