tetra-O-acetyl-6-deoxy-L-mannose diphenyldithioacetal | 30571-59-6

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: tetra-O-acetyl-6-deoxy-L-mannose diphenyldithioacetal
• 英文别名: (2R,3R,4S,5S)-1,1-bis(phenylthio)hexane-2,3,4,5-tetrayl tetraacetate；2,3,4,5-Tetra-O-acetyl-6-deoxy-L-mannose-diphenyldithioacetal；[(2S,3S,4R,5R)-3,4,5-triacetyloxy-6,6-bis(phenylsulfanyl)hexan-2-yl] acetate
• CAS: 30571-59-6
• 化学式: C₂₆H₃₀O₈S₂
• 分子量: 534.651
• InChiKey: BFAVQHHIIZBXJK-SPURNAMPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  36
• 可旋转键数：
  16
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  156
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  tetra-O-acetyl-6-deoxy-L-mannose diphenyldithioacetal 在 1,5,7-三氮杂双环[4.4.0]癸-5-烯 作用下， 以 氘代二甲亚砜 为溶剂， 反应 18.0h， 以74%的产率得到(2S,3R,4S)-6,6-bis(phenylthio)hex-5-ene-2,3,4-triyl triacetate
  参考文献：
  名称：

  温和条件下糖硫缩醛的区域选择性脱水

  摘要：

  糖类在废弃生物质中含量丰富，使它们成为有机合成的可持续手性构件。药物应用对手性饱和杂环的需求正在增加，因为它们提供了明确的三维框架，显示出更高的代谢抗性。一系列糖硫缩醛可以在温和的碱性条件下在 C-2 处选择性脱水，所得的烯酮硫缩醛可以通过进一步的选择性脱水反应用于生产有用的手性结构单元。

  DOI：

  10.1021/acs.orglett.1c00424
• 作为产物：
  描述：

  L-rhamnopyranose 以 三氟乙酸 为溶剂， 反应 3.0h， 生成 tetra-O-acetyl-6-deoxy-L-mannose diphenyldithioacetal
  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：——