卡培他滨中间体 | 38838-07-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 卡培他滨中间体
• 英文名称: methyl 5-chloro-5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside
• 英文别名: methyl 5-chloro-5-deoxy-2,3-O-isopropylidene-β-D-riboside；1-O-methyl-2,3-O-isopropylidene-5-chloro-5-deoxy-β-D-ribofuranoside；Methyl 5-chloro-5-deoxy-2,3-O-(1-methylethylidene)-I(2)-D-ribofuranoside；(3aR,4R,6S,6aS)-6-(chloromethyl)-4-methoxy-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole
• CAS: 38838-07-2
• 化学式: C₉H₁₅ClO₄
• 分子量: 222.669
• InChiKey: IKMCNTFVIGEWGJ-WCTZXXKLSA-N

物化性质

• 沸点：
  278.4±40.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  卡培他滨中间体 在 双(三甲基硅烷基)氨基钾 、 (S)-叔丁基 2-(叔丁氧基羰基氨基)-4-疏基丁酸酯 作用下， 以 四氢呋喃 为溶剂， 反应 8.0h， 生成 methyl 5-deoxy-2,3-O-isopropylidene-β-D-erythro-pent-4-enofuranoside
  参考文献：
  名称：

  Revisiting synthetic preparation of the quorum sensing substrate S-d-ribosyl-l-homocysteine (SRH)

  摘要：

  Cleavage of the thioether bond of S-D-ribosyl-L-homocysteine (SRH) by the enzyme S-ribosylhomocysteinase (LuxS) serves as the final biosynthetic step in the generation of the quorum sensing autoinducer AI-2 by bacteria. Herein, a revised chemical synthesis of SRH is presented at convenient scale and purity for in vitro studies of LuxS. Potassium bis(trimethylsilyl) amide (KHMDS) is identified as a judicious base for the formation of the thioether of the target compound from readily-accessible precursors: a thiol nucleophile derived from L-homocystine and a sulfonate-activated D-ribosyl electrophile. The exclusive use of acid-labile protecting groups allows for facile deprotection to the final product, producing the TFA salt of SRH in five synthetic steps and 26% overall yield. The chemically-synthesized material is isolated at high purity and demonstrated to serve as the LuxS substrate by an in vitro assay. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.05.009
• 作为产物：
  描述：

  卡培他滨杂质25 在 吡啶 、 硫酸 、 lithium chloride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 51.5h， 生成 卡培他滨中间体
  参考文献：
  名称：

  核糖基离子液体的结构性质关系

  摘要：

  这项工作的作者成功地合成了多种新的基于核糖的离子液体，在碳水化合物的不同位置使用不同的保护基（甲基，乙基，烯丙基和苄基），以及不同的季铵化N-杂环和不同阴离子。碳水化合物基离子液体（CHIL）的这些一致的变化使得能够进行广泛的热性质结构-性质关系研究，从而使作者能够证明现有的趋势并发现分解温度与CHILs结构之间的相关性。

  DOI：

  10.1016/j.molliq.2020.115167

文献信息

• 5'-SUBSTITUTED-RIBOFURANOSYL BENZIMIDAZOLES AS ANTIVIRAL AGENTS
  申请人：——

  公开号：US20010011075A1

  公开（公告）日：2001-08-02

  The present invention relates to polysubstituted benzimidazoles, having the following formula: 1 wherein Q is a substituted benzimidazole group attached at the benzimidazole 1-position; R is a halogen of atomic number 9 to 53, inclusive (i.e., —F, —Cl, —Br, or —I); azido (i.e., —N 3 ); or —X—R 1 , wherein X is a chalcogen of atomic number 8 to 16, inclusive (i.e., —O— or —S—), and R 1 may be straight or branched chain alkyl of 1 to 8 carbon atoms; and R 2 and R 3 may be the same or different and are separately —O—C(═O)CH 3 (i.e., —OAc) or hydroxy (i.e., —OH); and pharmaceutically acceptable salts and operative combinations thereof. Also provided by this invention are compositions comprising a polysubstituted benzimidazole as defined above and methods of use thereof.

  本发明涉及具有下式的多取代苯并咪唑： 1 其中 Q 是连接在苯并咪唑 1 位上的取代苯并咪唑基团；R 是原子序数为 9 至 53（含）的卤素（即 -F、-Cl、-Br 或 -I）；叠氮（即 -N 3 ）；或 -X-R 1 其中 X 是原子序数为 8 至 16（包括 8 和 16）的缩醛（即 -O- 或 -S-），而 R 1 可以是 1 至 8 个碳原子的直链或支链烷基；以及 R 2 和 R 3 可以相同或不同，并分别为-O-C(═O)CH 3 (即-OAc)或羟基(即-OH)；以及药学上可接受的盐及其作用组合。本发明还提供了包含如上定义的多取代苯并咪唑的组合物及其使用方法。
• Design and Reactivity of Organic Functional Groups — 2-Pyridylsulfonates as Nucleofugal Esters: Remarkably Mild Transformations into HAlides and Olefins
  作者：Stephen Hanessian、Masahiro Kagotani、Kossi Komaglou

  DOI：10.3987/com-88-s134

  日期：——
• Synthesis and Antiviral Activity of Certain 5‘-Modified Analogs of 2,5,6-Trichloro-1-(β-<scp>d</scp>-ribofuranosyl)benzimidazole
  作者：Kristjan S. Gudmundsson、John C. Drach、Linda L. Wotring、Leroy B. Townsend

  DOI：10.1021/jm9604888

  日期：1997.2.1

  A series of 5'-modified 2,5,6-trichlorobenzimidazole ribonucleosides has been synthesized and tested for activity against two human herpesviruses and for cytotoxicity. The 5'-methoxy, 5'-ethoxy, and 5'-butoxy analogs of 2,5,6-trichloro-1-(beta-D-ribofuranosyl)benzimidazole (TCRB) were prepared by coupling the appropriate 5-O-alkyl-1,2,3-tri-O-acetyl-beta-D-ribose derivatives with 2,5,6-trichlorobenzimidazole followed by removal of the protecting groups. The 5'-deoxy-5'-fluoro, -5'-chloro, -5'-bromo, -5'-iodo, -5'-azido, and -5'-thiomethyl derivatives were synthesized in a similar fashion. All of these 5'-modified derivatives had significant activity against HCMV in plaque and yield reduction assays (IC50's = 0.5-14.2 mu M) but had little activity (IC50's > 100 mu M) against HSV-1. This pattern is similar to the antiviral activity profile observed for TCRB. The 5'-halogenated derivatives were more active than the other 5'-modified derivatives with antiviral activity well separated from cytotoxicity. In general, cytotoxicity of all the 5'-modified derivatives was greater in human foreskin fibroblasts (HFF cells) than in L1210 or K-B tumor cells. These results indicate that the viral target tolerates significant modifications of TCRB at the 5'-position without adversely affecting activity against HCMV, whereas the 5'-modifications increased cytotoxicity in human diploid cells.
• ——
  作者：Robert V. Stick、Keith A. Stubbs、D. Matthew G. Tilbrook

  DOI：10.1071/ch01036

  日期：——

  An efficient synthesis of (R)-2,3-dihydroxypropyl 5-deoxy-5-dimethylarsinyl-beta -D-riboside, a common marine arsenical, from D-ribose, (S)-2,3-dibenzyloxypropanol and iododimethylarsine is described.
• US5874413A
  申请人：——

  公开号：US5874413A

  公开（公告）日：1999-02-23