Title:
PRODUCTION OF 1ALPHA,25-DIHYDROXYVITAMINS D4 AND D7
Document Type and Number:
Japanese Patent JP3483155
Kind Code:
B2
Abstract:
PURPOSE: To obtain the subject compounds having differentiation-inducing activity and osteogenetic activity by converting a 22C alcohol derivative obtained from stigmasterol into a 5,7-diene modification via several processes followed by subjecting the 5,7-diene modification to ultraviolet-light irradiation and thermal isomerization successively.
CONSTITUTION: A 22C alcohol derivative of formula I (Ph denotes phenyl) obtained from stigmasterol is tosylated and then treated with NaI to convert into a 22-iodine modification, which is then condensed with a sulfone derivative of formula II (R1 is methyl or H; R2 is H or methyl; Et denotes ethyl) to produce a 23-phenylsulfone derivative of formula III. This derivative is then subjected to reductive desulfurization followed by selectively α-epoxidize the double bond of the derivative of formula III, and the protecting group for the hydroxyl group of this compound is eliminated to convert into a diol compound followed by reducing the epoxy group of the diol compound to change into a triol compound, which is, in turn, subjected to ultraviolet-light irradiation and thermal isomerization successively, thus obtaining the objective 1α,25- dinydroxyvitamins D4 and D7 of formula IV.
Inventors:
Yoji Tachibana
Shinji Yokoyama
Takeshi Teshima
Shinji Yokoyama
Takeshi Teshima
Application Number:
JP25658593A
Publication Date:
January 06, 2004
Filing Date:
October 14, 1993
Export Citation:
Assignee:
Nisshin Flour Milling Group Inc.
International Classes:
C07C401/00; C07J9/00; C07J75/00; (IPC1-7): C07C401/00; C07J9/00
Domestic Patent References:
| JP4300865A | ||||
| JP5163238A | ||||
| JP3141293A |
Other References:
Ｂｕｌｌ．Ｃｈｅｍ．Ｓｏｃ．Ｊｐｎ．，１９９０，Ｖｏｌ．６３，Ｎｏ．８，Ｐ２２３３−３８
日本化学会誌，１９９２，Ｎｏ．１，Ｐ５３−６２
日本化学会誌，１９９２，Ｎｏ．１，Ｐ５３−６２
Attorney, Agent or Firm:
Chika Takagi (2 outside)