微流光反应技术制备树脂状维生素D3

doi:10.7517/j.issn.1674-0475.2017.04.027

影像科学与光化学 ›› 2017, Vol. 35 ›› Issue (5): 667-674.DOI: 10.7517/j.issn.1674-0475.2017.04.027

微流光反应技术制备树脂状维生素D₃

李超, 周前雄, 张宝文, 王雪松

中国科学院理化技术研究所光化学转换与功能材料重点实验室, 北京 100190

收稿日期:2017-05-27 修回日期:2017-06-15 出版日期:2017-09-15 发布日期:2017-09-15
通讯作者: 李超, 王雪松

Preparation of Resin-like Vitamin D₃ by Micro-flow Photoreaction

LI Chao, ZHOU Qianxiong, ZHANG Baowen, WANG Xuesong

Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China

Received:2017-05-27 Revised:2017-06-15 Online:2017-09-15 Published:2017-09-15

摘要/Abstract

摘要：

合成维生素D₃的关键步骤是7-去氢胆固醇光照开环合成预维生素D₃，目前合成是在釜式光反应器中进行，原料转化率低，产物提纯难度大，产品生产周期长。本文利用微流光反应技术开展预维生素D₃的制备研究，与传统釜式光反应器相比，原料转化率从低于30%提高到95%，光照产物无需纯化，可直接通过热异构化反应制备树脂状维生素D₃，生产周期大为缩短。

关键词: 维生素D₃, 7-去氢胆固醇, 预维生素D₃, 微流光化学反应器

Abstract:

The key process in the synthesis of vitamin D₃ is the photochemical conversion from 7-dehydrocholesterol to pre-vitamin D₃, which is currently carried out in batch photoreactors and suffers from low conversion efficiency, recycle of unreacted 7-dehydrocholesterol, and long production period. Using micro-flow photoreactor instead of batch photoreactor, the conversion yield of 7-dehydrocholesterol may be increased from less than 30% to over 95%,allowing the photoreaction product to be directly used to prepare resin-like vitamin D₃ through a thermal isomerization reaction and shortening the production period greatly.

Key words: vitamin D₃, 7-dehydrocholesterol, pre-vitamin D₃, micro-flowphotoreactor

李超, 周前雄, 张宝文, 王雪松. 微流光反应技术制备树脂状维生素D₃[J]. 影像科学与光化学, 2017, 35(5): 667-674.

LI Chao, ZHOU Qianxiong, ZHANG Baowen, WANG Xuesong. Preparation of Resin-like Vitamin D₃ by Micro-flow Photoreaction[J]. Imaging Science and Photochemistry, 2017, 35(5): 667-674.

参考文献

[1] Tian J, Liu Y, Williarns L A, de Zeeuw D. Potential role of active vitamin D inretarding the progression of chronic kidney is easing[J].Nephrology Dialysis Transplantation, 2007,22:321-328.
[2] Adams T H, Noman A W. Studies on the mechanism of action of calciferol[J]. Journal of Biological Chemistry, 1970, 245:4421-4431.
[3] Prüfer K, Racz A, Lin G C, Barsony J. Dimerization with retinoid X receptors promotes nuclear localization and subnuclear targeting of vitamin D receptors[J]. Journal of Biological Chemistry, 2000, 275:41114-41123.
[4] Wang T J, Pencina M J, Booth S L, Jacques P F, Ingelsson E, Lanier K, Benjamin E J, D'Agostino R B, Wolf M, Vasan R S. Vitamin D deficiency and risk of cardiovascular disease[J]. Circulation, 2008, 117:503-511.
[5] Mietinen M E, Reinert L, Kinnunen L, Harjutsalo V, Koskela P, Surcel H M, Lamberg-Allardt C, Tuomilehto J. Serum 25-hydroxyvitamin D level during early pregnancy and type Idiabetes risk in the offspring[J].Diabetologia, 2012, 55:1291-1294.
[6] 张宝文,程学新,刘颙颙,王雪松,曹怡.光化学合成VD₃的方法[P]. 中国专利,ZL02104444.9.2002-03-18. Zhang B W, Cheng X X, Liu R R, Wang X S, Cao Y. The synthesis method of VD₃ by photochemistry[P].Chinese patent, ZL02104444.9.2002-03-18.
[7] Sumino S, Uno M, Fukuyama T, Ryu I, Matsuura M, Yamamoto A, Kishikawa Y. Photoredox-catalyzed hydro-difluoroalkylation of alkenes using difluorohaloalkyl compounds and a hantzsch ester[J].Journal of Organic Chemi-stry,2017,82:5469-5474.
[8] Lu H, Schmidt M A, Jensen K F. Photochemical reactions and on-line UV detection in microfabricated reactors[J].Lab on a Chip, 2001, 1:22-28.
[9] Wojcik F, O'Brien A G, G tze S,Seeberger P H. Hartmann L, Synthesis of carbohydrate-functionalized sequence-defined Oligo(amidoanine)s by photochemical thiol-ene coupling in a continuous flow reactor[J].Chemistry-A European Journal, 2013, 19:3090-3098.
[10] Andrews R S, Becker J J, Gagné M R. A photoflow reactor for the continuous photoredox-mediated synthesis of C-glycoamino acids and C-glycolipids[J]. Angewandte Chemie International Edition, 2012, 51:4140-4143.
[11] Kopetzki D, Lévesque F, Seeberger P H. A continuous-flow process for the synthesis of artemisinin[J].Chemistry-A European Journal, 2013, 19:5450-5456.

微流光反应技术制备树脂状维生素D₃

Preparation of Resin-like Vitamin D₃ by Micro-flow Photoreaction

PDF (PC)

可视化

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 2

编辑推荐

Metrics

本文评价

[1]	张栋, 吴骊珠, 张丽萍, 佟振合. 以Nafion负载的三联吡啶铂络合物为敏化剂光敏氧化7-去氢胆固醇[J]. 影像科学与光化学, 2003, 21(6): 405-411.
[2]	高云燕, 游长江, 陈金平, 李嫕. 硅胶固载光敏剂的合成及其在反式维生素D₃光敏异构化为顺式维生素D₃中的应用[J]. 影像科学与光化学, 2003, 21(1): 20-24.