L-rhamnose-1,1-dimethylene-dithioacetal | 40733-09-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二硫杂环戊烷
• 英文名称: L-rhamnose-1,1-dimethylene-dithioacetal
• 英文别名: 6-deoxy-L-mannose ethylenedithioacetal；(1R,2R,3S,4S)-1-(1,3-dithiolan-2-yl)pentane-1,2,3,4-tetrol
• CAS: 40733-09-3
• 化学式: C₈H₁₆O₄S₂
• 分子量: 240.345
• InChiKey: FOQSWOQCFBCQCX-VWDOSNQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  132
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  L-rhamnose-1,1-dimethylene-dithioacetal 在 硫酸 、 sodium hydride 作用下， 反应 28.0h， 生成 2,5-di-O-benzyl-3,4-di-O-methyl-L-rhamnose-1,1-dimethylene dithioacetal
  参考文献：
  名称：

  Vishwanadham, G, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 9, p. 624 - 625

  摘要：

  DOI：
• 作为产物：
  描述：

  L-rhamnopyranose 、 1,2-乙二硫醇 在 三氟化硼乙醚 作用下， 以 溶剂黄146 为溶剂， 反应 1.0h， 以36%的产率得到L-rhamnose-1,1-dimethylene-dithioacetal
  参考文献：
  名称：

  Application of molecular mechanics in the total stereochemical elucidation of spicigerolide, a cytotoxic 6-tetraacetyloxyheptenyl-5,6-dihydro-α-pyrone from Hyptis spicigera

  摘要：

  Bioactivity-directed fractionation of the crude extract prepared from the medicinal Mexican plant Hyptis spicigera (Lamiaceae) tested on KB cells led to the isolation of spicigerolide (1). The structure for this novel cytotoxic compound was elucidated as 6R-[3S,4S,5S,6S-tetraacetyloxy-1Z-heptenyl]-5,6-dihydro-2H-pyran-2-one. The relative stereochemistry of this flexible molecule was determined by a combination of molecular mechanics calculations and H-1-H-1 coupling constant data, while the absolute configuration was established according to CD measurements. The MM/(3)J(H-H) calculations, as applied to 1, was validated with model Linear compounds prepared from L-rhamnose: 2,3,4,5-tetra-O-acetyl-6-deoxy-L-mannose (5) and tetra-O-acetyl-1,6-dideoxy-L-mannitol (8). Both compounds possess the same stereochemistry predicted to be present in the acyclic moiety of spicigerolide (1) but lacking the stereochemical influence of the chiral pyrone. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(00)00987-x

文献信息

• Fragoso-Serrano, Mabel; Guillen-Jaramillo, Georgina; Pereda-Miranda, Rogelio, Journal of Organic Chemistry, 2003, vol. 68, # 19, p. 7167 - 7175
  作者：Fragoso-Serrano, Mabel、Guillen-Jaramillo, Georgina、Pereda-Miranda, Rogelio、Cerda-Garcia-Rojas, Carlos M.

  DOI：——

  日期：——
• Application of molecular mechanics in the total stereochemical elucidation of spicigerolide, a cytotoxic 6-tetraacetyloxyheptenyl-5,6-dihydro-α-pyrone from Hyptis spicigera
  作者：Rogelio Pereda-Miranda、Mabel Fragoso-Serrano、Carlos M Cerda-Garcı́a-Rojas

  DOI：10.1016/s0040-4020(00)00987-x

  日期：2001.1

  Bioactivity-directed fractionation of the crude extract prepared from the medicinal Mexican plant Hyptis spicigera (Lamiaceae) tested on KB cells led to the isolation of spicigerolide (1). The structure for this novel cytotoxic compound was elucidated as 6R-[3S,4S,5S,6S-tetraacetyloxy-1Z-heptenyl]-5,6-dihydro-2H-pyran-2-one. The relative stereochemistry of this flexible molecule was determined by a combination of molecular mechanics calculations and H-1-H-1 coupling constant data, while the absolute configuration was established according to CD measurements. The MM/(3)J(H-H) calculations, as applied to 1, was validated with model Linear compounds prepared from L-rhamnose: 2,3,4,5-tetra-O-acetyl-6-deoxy-L-mannose (5) and tetra-O-acetyl-1,6-dideoxy-L-mannitol (8). Both compounds possess the same stereochemistry predicted to be present in the acyclic moiety of spicigerolide (1) but lacking the stereochemical influence of the chiral pyrone. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Vishwanadham, G, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1992, vol. 31, # 9, p. 624 - 625
  作者：Vishwanadham, G

  DOI：——

  日期：——