200636-54-0Relevant articles and documents
Synthesis of 2α-and 2β-substituted-14-epi-previtamin D 3 and their genomic activity
Sawada, Daisuke,Katayama, Tomoyuki,Tsukuda, Yuya,Saito, Nozomi,Saito, Hiroshi,Takagi, Ken-Ichiro,Ochiai, Eiji,Ishizuka, Seiichi,Takenouchi, Kazuya,Kittaka, Atsushi
scheme or table, p. 5407 - 5423 (2010/08/19)
2α-and 2α-Substituted analogs of 14-epi-previtamin D3 were synthesized and isolated after thermal isomerization of 14-epi-vitamin D3 triene at 80 °C.The VDR binding affinity and transactivation activity of osteocalcin promoter in HOS cells were tested, and the 2a-methyl-substituted analog was found to have greater genomic activity than 14-epi-previtamin D 3.We found that modification at the C2 position of the seco-steroidal skeleton afforded interesting effects for biological genomic activity for the pre-vitamin D form as well as the natural vitamin D form.
Parallel synthesis of a vitamin D3 library in the solid-phase
Hijikuro,Doi,Takahashi
, p. 3716 - 3722 (2007/10/03)
A highly efficient synthesis of the vitamin D3 system on solid support is described. Two synthetic strategies for the solid-phase synthesis of vitamin D3 were developed. One is for 11-hydroxy analogues, and the other is for most other synthetic analogues. In the latter strategy, the sulfonate-linked CD-ring 58 was initially immobilized on PS-DES resin to give solid-supported CD-ring 63 (Scheme 10). Similarly, solid-supported CD-ring 63 was prepared by attachment of the CD-ring 10 to the chlorosulfonate resin 64. The vitamin D3 system was synthesized by Horner-Wadsworth-Emmons reaction of the A-ring phosphine oxide to a solid-supported CD-ring, followed by simultaneous introduction of the side chain and cleavage from resin with a Cu1-catalyzed Grignard reagent. Parallel synthesis of the vitamin D3 analogues was accomplished by a split and pool methodology utilizing radio frequency encoded combinatorial chemistry, and a manual parallel synthesizer for side chain diversification and deprotection. Additionally, we demonstrated the synthesis of various A-rings in a similar protocol for efficient preparation of building blocks.
