methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-α-D-arabino-hex-2-ulopyranosyl isothiocyanate)onate | 874460-63-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-α-D-arabino-hex-2-ulopyranosyl isothiocyanate)onate
• 英文别名: methyl (3aR,6R,7S,7aR)-7-benzoyloxy-6-isothiocyanato-2,2-dimethyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-carboxylate
• CAS: 874460-63-6
• 化学式: C₁₈H₁₉NO₇S
• 分子量: 393.417
• InChiKey: XZQGVFQJKFCJDO-ZUMXRPEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-α-D-arabino-hex-2-ulopyranosyl isothiocyanate)onate 、 甲氧苯胺 以 四氢呋喃 为溶剂， 反应 2.0h， 以72%的产率得到(5R,8R,9R,10S)-10-benzoyloxy-8,9-dimethylmethylenedioxy-3-p-methoxyphenyl-4-oxo-2-thioxo-6-oxa-1,3-diazaspiro[4.5]decane
  参考文献：
  名称：

  Stereocontrolled synthesis of thiohydantoin spironucleosides from sugar spiroacetals

  摘要：

  5-Epithiohydantocidin, N-alkyl and N-glycosylthiohydantoin spironucleosides are prepared from glycosylaminoesters and from furanoid and pyranoid methyl isothiocyanatoulosonates. The aminoesters; and the isothiocyanates are obtained, in a stereocontrolled manner, from sugar spiroacetals through a high-yielding sequence involving ring opening with trimethyl azide, formation of an ester group, reduction of the azide, and, in the case of isothiocyanates, reaction with thiophosgene. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.128
• 作为产物：
  描述：

  methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-β-D-arabino-hex-2-ylopyranosyl azide)onate 在 palladium on activated charcoal 氢气 、 calcium carbonate 作用下， 以 甲醇 、 水 为溶剂， 反应 73.0h， 生成 methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-α-D-arabino-hex-2-ulopyranosyl isothiocyanate)onate
  参考文献：
  名称：

  Stereocontrolled synthesis of thiohydantoin spironucleosides from sugar spiroacetals

  摘要：

  5-Epithiohydantocidin, N-alkyl and N-glycosylthiohydantoin spironucleosides are prepared from glycosylaminoesters and from furanoid and pyranoid methyl isothiocyanatoulosonates. The aminoesters; and the isothiocyanates are obtained, in a stereocontrolled manner, from sugar spiroacetals through a high-yielding sequence involving ring opening with trimethyl azide, formation of an ester group, reduction of the azide, and, in the case of isothiocyanates, reaction with thiophosgene. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.128

文献信息

• Stereocontrolled synthesis of thiohydantoin spironucleosides from sugar spiroacetals
  作者：José Fuentes、Bader A.B. Salameh、M. Angeles Pradera、Francisco J. Fernández de Córdoba、Consolación Gasch

  DOI：10.1016/j.tet.2005.09.128

  日期：2006.1

  5-Epithiohydantocidin, N-alkyl and N-glycosylthiohydantoin spironucleosides are prepared from glycosylaminoesters and from furanoid and pyranoid methyl isothiocyanatoulosonates. The aminoesters; and the isothiocyanates are obtained, in a stereocontrolled manner, from sugar spiroacetals through a high-yielding sequence involving ring opening with trimethyl azide, formation of an ester group, reduction of the azide, and, in the case of isothiocyanates, reaction with thiophosgene. (c) 2005 Elsevier Ltd. All rights reserved.