Two novel approaches toward stereoselective introduction of beta-hydroxymethyl group at the C-7 position of 5-androstene
文献类型：期刊论文
| 作者 | Gu, Q; Zheng, YH; Li, YC |
| 刊名 | SYNTHESIS-STUTTGART
 |
| 出版日期 | 2006-03-17 |
| 期号 | 6页码:975-978 |
| 关键词 | steroids stereoselective 7 beta-hydroxymethyl 5-androstene ionic hydrogenation |
| ISSN号 | 0039-7881 |
| DOI | 10.1055/s-2006-926356 |
| 文献子类 | Article |
| 英文摘要 | Two novel approaches to stereoselective introduction of 7 beta-hydroxymethyl group onto 5-androstene have been developed. In the first approach, coupling of benzyloxymethyl chloride with the 7-carbonyl group of 1 mediated by Sml(2) lives, after debenzylation, two isomers 4 and 5 respectively, which are stereoselectively deoxygenated by means of ail ionic hydrogenation to afford 6. The second approach involves the addition of (isopropoxydimethylsilyl)methyl Grignard reagent (Tamao's reagent) to the 7-carbonyl group of 1, followed by oxidative cleavage of the silicon-carbon bond by hydrogen peroxide giving compound 5. Stereoselective deoxygenation of 5 via an ionic hydrogenation also affords 6. The relative configuration of 6 is confirmed by ROESY studies. |
| WOS关键词 | DERIVATIVES |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000236253900010 |
| 出版者 | GEORG THIEME VERLAG KG |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/273643]  |
| 专题 | 药物化学研究室 |
| 通讯作者 | Li, YC |
| 作者单位 | Chinese Acad Sci, Shanghai Inst Biol Sci, Inst Mat Med, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Gu, Q,Zheng, YH,Li, YC. Two novel approaches toward stereoselective introduction of beta-hydroxymethyl group at the C-7 position of 5-androstene[J]. SYNTHESIS-STUTTGART,2006(6):975-978. |
| APA | Gu, Q,Zheng, YH,&Li, YC.(2006).Two novel approaches toward stereoselective introduction of beta-hydroxymethyl group at the C-7 position of 5-androstene.SYNTHESIS-STUTTGART(6),975-978. |
| MLA | Gu, Q,et al."Two novel approaches toward stereoselective introduction of beta-hydroxymethyl group at the C-7 position of 5-androstene".SYNTHESIS-STUTTGART .6(2006):975-978. |
入库方式： OAI收割
来源：上海药物研究所
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