Short Synthesis of (+)-1-Deoxynojirimycin via a Diastereoselective Reductive Coupling of Alkyne and alpha-Chiral Aldehyde
文献类型：期刊论文
| 作者 | Zhou, Bing ; Tang, Huanyu; Feng, Huijin; Li, Yuanchao
|
| 刊名 | SYNLETT
 |
| 出版日期 | 2011-11 |
| 期号 | 18页码:2709-2712 |
| 关键词 | (+)-1-deoxynojirimycin diastereoselective coupling L-isoserine diastereoselective synthesis chelation-control transition state |
| ISSN号 | 0936-5214 |
| DOI | 10.1055/s-0031-1289546 |
| 文献子类 | Article |
| 英文摘要 | A short, highly diastereoselective synthesis of (+)-1-deoxynojirimycin from readily available L-isoserine with overall yield of 32.0% in eight steps is described. The key step includes a diastereoselective syn-coupling reaction of Cbz-protected (S)-isoserinal acetonide 6 and vinylzinc nucleophile, generated conveniently from a protected propargyl alcohol 7 by a hydrozirconation-transmetalation sequence. Significantly, not only does this simple flexible strategy provide a concise approach to (+)-1-deoxynojirimycin, but it also can readily be adopted for the synthesis of other stereoisomers of the 1-deoxynojirimycin family from L- or D-isoserine through different coupling conditions and stereoselective epoxidation of allylic alcohol 4 by the same procedures. |
| WOS关键词 | L-DEOXYMANNOJIRIMYCIN ; ASYMMETRIC INDUCTION ; INHIBITOR ; ACCESS ; 1-DEOXYNOJIRIMYCIN ; DEOXYNOJIRIMYCIN ; STEREOCHEMISTRY ; BIOSYNTHESIS ; NOJIRIMYCIN ; IMINOSUGARS |
| 资助项目 | 'Key New Drug Creation and Manufacturing Program', China[2009ZX09102-026] |
| WOS研究方向 | Chemistry |
| 语种 | 英语 |
| WOS记录号 | WOS:000296746800021 |
| 出版者 | GEORG THIEME VERLAG KG |
| 源URL | [http://119.78.100.183/handle/2S10ELR8/278356]  |
| 专题 | 药物化学研究室 |
| 通讯作者 | Li, Yuanchao |
| 作者单位 | Chinese Acad Sci, Shanghai Inst Mat Med, Shanghai 201203, Peoples R China |
| 推荐引用方式 GB/T 7714 | Zhou, Bing,Tang, Huanyu,Feng, Huijin,et al. Short Synthesis of (+)-1-Deoxynojirimycin via a Diastereoselective Reductive Coupling of Alkyne and alpha-Chiral Aldehyde[J]. SYNLETT,2011(18):2709-2712. |
| APA | Zhou, Bing,Tang, Huanyu,Feng, Huijin,&Li, Yuanchao.(2011).Short Synthesis of (+)-1-Deoxynojirimycin via a Diastereoselective Reductive Coupling of Alkyne and alpha-Chiral Aldehyde.SYNLETT(18),2709-2712. |
| MLA | Zhou, Bing,et al."Short Synthesis of (+)-1-Deoxynojirimycin via a Diastereoselective Reductive Coupling of Alkyne and alpha-Chiral Aldehyde".SYNLETT .18(2011):2709-2712. |
入库方式： OAI收割
来源：上海药物研究所
浏览0
下载0
收藏0
其他版本
除非特别说明，本系统中所有内容都受版权保护，并保留所有权利。