Couphng of the CD fragment, ketone 6 (obtamed by pamal synthesis from vitanun D2). either directly (Homer-Wmlg route) or via the denved enol mflate (dlenyne route) with the appropnate A-ring fragment, phosphme oxide amon 7 or enyne 10, 1s the key step m the syntheses of 24-oxavmunm D3 (ld) and la-hy
Synthesis of tritiated 1α,25-dihydroxy-22-oxavitamin D3
✍ Scribed by Hiroyoshi Watanabe; Masashi Akiyama; Takehiko Kawanishi; Noboru Kubodera
- Publisher
- John Wiley and Sons
- Year
- 1995
- Tongue
- French
- Weight
- 563 KB
- Volume
- 36
- Category
- Article
- ISSN
- 0022-2135
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✦ Synopsis
Abstract
Synthesis of two tritiated 1α,25‐dihydroxy‐22‐oxavitamin D~3~ (OCT), [26‐^3^H~3~]OCT (3) and [2β‐^3^H]OCT (4), is described. [26‐^3^H~3~]OCT (3) was prepared by tritiation at the side chain with tritiated methylmagnesium iodide and [2β‐^3^H]OCT (4) was labeled at the A‐ring by tritiation with sodium borotritiide.
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We describe a convergent synthesis of 1ct,25-dihydr(.xy-19-norprevitamin I)3 (3), an analogue of the hormone lct,25-dihydroxyvitamin D3 (lc) that is locked into the previtamin form.
An efficient synthesis of the title compound is reported based on C-l functionalization of the triazoline Diels-Alder adduct of 25-OH previtamin D3 (2). lu,25-Dihydroxy vitamin D3 (la) is considered as the most important and active natural metabolite of vitamin D 1 3 -Recently we have described a no