Two new vitamin D isomers. Formation of (3S,10R)-(Z,Z)-9,10-secocholesta-5,7,14-trien-3-ol and its 10S-epimer from cis-isotachysterol3 via facile [1,7]sigmatropic rearrangements

Onisko, Bruce; Schnoes, Heinrich K.; DeLuca, Hector F.

doi:10.1021/jo00412a002

Cited by 8 publications

(1 citation statement)

References 3 publications

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“…In einer vor kurzem erschienenen Mitteilung wird uber die thermisch erlaubte Wasserstoffwanderung von 5,6 (a-Isotachysterin zu einem neuen konjugierten Trien, dem (3S, 10R)-bzw. (3S, 10s)-(Z, Z)-9,10-Secocholesta-5,14,17trien-3P-01, berichtet [5]. Okumura et al [6] klarten die Konfiguration der durch chemische Reduktion gewonnenen Dihydrotachysterine anhand der Analyse der Kernresonanzspektren auf.…”

Section: Discussionunclassified

9, 10‐Secocholesta‐(5Z)‐5,8(14), 10(19)‐trien‐3β‐ol und 18‐Nor‐14β‐methyl‐9,10‐secocholesta‐(5E)‐5, 10(19), 13(17)‐trien‐3β‐ol, zwei neue Doppelbindungsisomere des Vitamins D₃. Strukturelle Abwandlungen am Vitamin D₃: 5. Mitteilung [1]

Reischl

Zbiral

1980

Helvetica Chimica Acta

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9,10‐Secocholesta‐(5Z)‐5,8(14),10(19)‐triene‐3β‐ol and 18‐Nor‐14β‐methyl‐9,10‐secocholesta‐(5E)‐5,10(19), 13(17)‐trien‐3β‐ol, two new double bond isomers of vitamin D3. Structural modifications of vitamin D3: 5. Communication [1] The present paper reports the synthesis and structure elucidation of the two title compounds. Treatment of the 4‐phenyl‐1,2,4‐triazolin‐3,5‐dione adducts of vitamin D3 with BF3O (C2H5)2 and KOH/butanol yields these two new vitamin D3 double bond isomers.

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Section: Discussionunclassified

9, 10‐Secocholesta‐(5Z)‐5,8(14), 10(19)‐trien‐3β‐ol und 18‐Nor‐14β‐methyl‐9,10‐secocholesta‐(5E)‐5, 10(19), 13(17)‐trien‐3β‐ol, zwei neue Doppelbindungsisomere des Vitamins D₃. Strukturelle Abwandlungen am Vitamin D₃: 5. Mitteilung [1]

Reischl

Zbiral

1980

Helvetica Chimica Acta

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Investigation of Degradation Products and Extractables in Developing Topical OTC (Over the Counter) and NCE (New Chemical Entity) Consumer Healthcare Medication Products

Zhang

2011

Characterization of Impurities and Degradants Using Mass Spectrometry

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ChemInform Abstract: TWO NEW VITAMIN D ISOMERS. FORMATION OF (3S,10R)‐(Z,Z)‐9,10‐SECOCHOLESTA‐5,7,14‐TRIEN‐3‐OL AND ITS 10S‐EPIMER FROM CIS‐ISOTACHYSTEROL3 VIA FACILE (1,7)SIGMATROPIC REARRANGEMENTS

ONISKI¹,

Schnoes²,

DeLuca³

1979

Chemischer Informationsdienst

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Two new vitamin D isomers. Formation of (3S,10R)-(Z,Z)-9,10-secocholesta-5,7,14-trien-3-ol and its 10S-epimer from cis-isotachysterol3 via facile [1,7]sigmatropic rearrangements

Cited by 8 publications

References 3 publications

9, 10‐Secocholesta‐(5Z)‐5,8(14), 10(19)‐trien‐3β‐ol und 18‐Nor‐14β‐methyl‐9,10‐secocholesta‐(5E)‐5, 10(19), 13(17)‐trien‐3β‐ol, zwei neue Doppelbindungsisomere des Vitamins D₃. Strukturelle Abwandlungen am Vitamin D₃: 5. Mitteilung [1]

9, 10‐Secocholesta‐(5Z)‐5,8(14), 10(19)‐trien‐3β‐ol und 18‐Nor‐14β‐methyl‐9,10‐secocholesta‐(5E)‐5, 10(19), 13(17)‐trien‐3β‐ol, zwei neue Doppelbindungsisomere des Vitamins D₃. Strukturelle Abwandlungen am Vitamin D₃: 5. Mitteilung [1]

Investigation of Degradation Products and Extractables in Developing Topical OTC (Over the Counter) and NCE (New Chemical Entity) Consumer Healthcare Medication Products

ChemInform Abstract: TWO NEW VITAMIN D ISOMERS. FORMATION OF (3S,10R)‐(Z,Z)‐9,10‐SECOCHOLESTA‐5,7,14‐TRIEN‐3‐OL AND ITS 10S‐EPIMER FROM CIS‐ISOTACHYSTEROL3 VIA FACILE (1,7)SIGMATROPIC REARRANGEMENTS

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Two new vitamin D isomers. Formation of (3S,10R)-(Z,Z)-9,10-secocholesta-5,7,14-trien-3-ol and its 10S-epimer from cis-isotachysterol3 via facile [1,7]sigmatropic rearrangements

Cited by 8 publications

References 3 publications

9, 10‐Secocholesta‐(5Z)‐5,8(14), 10(19)‐trien‐3β‐ol und 18‐Nor‐14β‐methyl‐9,10‐secocholesta‐(5E)‐5, 10(19), 13(17)‐trien‐3β‐ol, zwei neue Doppelbindungsisomere des Vitamins D3. Strukturelle Abwandlungen am Vitamin D3: 5. Mitteilung [1]

9, 10‐Secocholesta‐(5Z)‐5,8(14), 10(19)‐trien‐3β‐ol und 18‐Nor‐14β‐methyl‐9,10‐secocholesta‐(5E)‐5, 10(19), 13(17)‐trien‐3β‐ol, zwei neue Doppelbindungsisomere des Vitamins D3. Strukturelle Abwandlungen am Vitamin D3: 5. Mitteilung [1]

Investigation of Degradation Products and Extractables in Developing Topical OTC (Over the Counter) and NCE (New Chemical Entity) Consumer Healthcare Medication Products

ChemInform Abstract: TWO NEW VITAMIN D ISOMERS. FORMATION OF (3S,10R)‐(Z,Z)‐9,10‐SECOCHOLESTA‐5,7,14‐TRIEN‐3‐OL AND ITS 10S‐EPIMER FROM CIS‐ISOTACHYSTEROL3 VIA FACILE (1,7)SIGMATROPIC REARRANGEMENTS

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9, 10‐Secocholesta‐(5Z)‐5,8(14), 10(19)‐trien‐3β‐ol und 18‐Nor‐14β‐methyl‐9,10‐secocholesta‐(5E)‐5, 10(19), 13(17)‐trien‐3β‐ol, zwei neue Doppelbindungsisomere des Vitamins D₃. Strukturelle Abwandlungen am Vitamin D₃: 5. Mitteilung [1]

9, 10‐Secocholesta‐(5Z)‐5,8(14), 10(19)‐trien‐3β‐ol und 18‐Nor‐14β‐methyl‐9,10‐secocholesta‐(5E)‐5, 10(19), 13(17)‐trien‐3β‐ol, zwei neue Doppelbindungsisomere des Vitamins D₃. Strukturelle Abwandlungen am Vitamin D₃: 5. Mitteilung [1]