1alpha,25-Dihydroxyvitamin D2 → Previtamin D3

HRID 1534195Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1534195
[CH3:1][C:2](O)([C@H:4](/[CH:6]=[CH:7]/[C@H:8]([C@@H:10]1[C@:27]2([CH3:28])[C@H:13]([C:14]3[C@H:24]([CH2:25][CH2:26]2)[C@:22]2([CH3:23])[C:17]([CH2:18][C@@H:19]([OH:30])[CH2:20][C@@H:21]2O)=[CH:16][CH:15]=3)[CH2:12][CH2:11]1)[CH3:9])C)[CH3:3].C[C@@H]([C@@H]1[C@@]2(C)CCC/C(=C\C=C3\C[C@@H](O)C[C@H](O)C\3=C)/[C@@H]2CC1)/C=C/[C@@H](C(O)(C)C)C>O1CCCC1.CCOCC>[CH3:23][C:22]1[CH2:21][CH2:20][C@H:19]([OH:30])[CH2:18][C:17]=1/[CH:16]=[CH:15]\[C:14]1[C@@H:13]2[CH2:12][CH2:11][C@H:10]([C@@H:8]([CH2:7][CH2:6][CH2:4][CH:2]([CH3:3])[CH3:1])[CH3:9])[C@@:27]2([CH3:28])[CH2:26][CH2:25][CH:24]=1

Komponenten

4

Edukt 2

HCID 95472431alpha,25-Dihydroxyvitamin D2HCID 67831887(22E)-5,7,22-Ergostatriene-1alpha,3beta,25-triol2×

Produkt 1

HCID 5281058Previtamin D3

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21868444Ether tetrahydrofuranLösungsmittel

Versuchsvorschrift

(22E)-5,7,22-Ergostatriene-1α,3β,25-triol and its 24-epimer of formula (I) can be converted into 1α,25-dihydroxyvitamin D2 and its 24-epimer of formula (II) by a general procedure for the synthesis of vitamin D from the 5,7-diene. More particularly, (22E)-5,7,22-ergostatriene-1α,3β,25-triol and its 24-epimer of formula (I) in tetrahydrofuran/ether were respectively irradiated to afford a previtamin D. The previtamin D was isomerized by heating in a suitable solvent, e.g. ethanol. Purification of the resulting products by chromatography and recrystallization affords 1α,25-dihydroxyvitamin D2 and the 24-epimer thereof.

Quellen und Nachweise

ORD-Eintrag
ord-4e1440997ddb4d73b18b9068c4334456
Quelldatensatz
uspto-grants-1992_02
Patentnummer
US05087709

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