(5R,8R,9R,10S)-10-benzoyloxy-8,9-dimethylmethylenedioxy-4-oxo-3-(2',3',4',6'tetra-O-acetyl-β-D-glucopyranosyl)-2-thioxo-6-oxa-1,3-diazaspiro[4.5]decane | 874460-67-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (5R,8R,9R,10S)-10-benzoyloxy-8,9-dimethylmethylenedioxy-4-oxo-3-(2',3',4',6'tetra-O-acetyl-β-D-glucopyranosyl)-2-thioxo-6-oxa-1,3-diazaspiro[4.5]decane
• 英文别名: [(3aR,6R,7S,7aR)-2,2-dimethyl-5'-oxo-2'-sulfanylidene-1'-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]spiro[3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6,4'-imidazolidine]-7-yl] benzoate
• CAS: 874460-67-0
• 化学式: C₃₁H₃₆N₂O₁₅S
• 分子量: 708.697
• InChiKey: XKHHJCZBMNBPDT-YQGHWFGTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  49
• 可旋转键数：
  13
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  233
• 氢给体数：
  1
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  (5R,8R,9R,10S)-10-benzoyloxy-8,9-dimethylmethylenedioxy-4-oxo-3-(2',3',4',6'tetra-O-acetyl-β-D-glucopyranosyl)-2-thioxo-6-oxa-1,3-diazaspiro[4.5]decane 在 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 36.0h， 以83%的产率得到(5R,8R,9R,10S)-10-benzoyloxy-8,9-dihydroxy-4-oxo-3-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-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：

  2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl isothiocyanate 、 methyl (3-O-benzoyl-2-deoxy-4,5-O-isopropylidene-α,β-D-arabino-hex-2-ulopyranosyl amine)onate 以 四氢呋喃 为溶剂， 反应 96.0h， 以76%的产率得到(5R,8R,9R,10S)-10-benzoyloxy-8,9-dimethylmethylenedioxy-4-oxo-3-(2',3',4',6'tetra-O-acetyl-β-D-glucopyranosyl)-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