(2R,3S,4R)-5,5-bis(ethylsulfanyl)-2,3,4-tris(phenylmethoxy)pentanal | 212691-31-1

• 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: (2R,3S,4R)-5,5-bis(ethylsulfanyl)-2,3,4-tris(phenylmethoxy)pentanal
• CAS: 212691-31-1
• 化学式: C₃₀H₃₆O₄S₂
• 分子量: 524.745
• InChiKey: FGUCNRBAOTVTOW-YTCPBCGMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  36
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  95.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R)-5,5-bis(ethylsulfanyl)-2,3,4-tris(phenylmethoxy)pentanal 在 正丁基锂 、 calcium carbonate 、 mercury dichloride 作用下， 以 水 、 乙腈 为溶剂， 生成 2,3,4-Tri-O-benzyl-5,6-dideoxy-L-arabino-hex-5-enose
  参考文献：
  名称：

  Selective 1,2-syn alkynylation of an open chain sugar: the prominent role of zinc chloride addition

  摘要：

  Depending on the metal, solvent and protective groups, functionalized aldehydes may react through either Felkin or chelated transition states leading to the Felkin Anh product or the 1,2-anti Felkin-Anh product. respectively. Zinc chloride addition proved to be a key aspect in order to favor 1,2-syn nucleophilic attack. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.03.061
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-D-galactose diethyldithioacetal 在 sodium periodate 作用下， 以 水 、 丙酮 为溶剂， 以56%的产率得到(2R,3S,4R)-5,5-bis(ethylsulfanyl)-2,3,4-tris(phenylmethoxy)pentanal
  参考文献：
  名称：

  Synthesis of an imidazolo-L-lyxo-piperidinose derivative

  摘要：

  Imidazolo-L-lyxo-piperidinose 4 was synthesised from the D-galactose derivative 8 by two reaction sequences via removal of a terminal carbon atom stepwise incorporation of an imidazole moiety, and eventually intramolecular S(N)2 reaction to the corresponding piperidine ring. Piperidinose 4 proved to be a poor glycosidase inhibitor. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00561-4

文献信息

• Synthesis of an imidazolo-L-lyxo-piperidinose derivative
  作者：Andrzej Frankowski、Dariusz Deredas、Jacques Streith、Théophile Tschamber

  DOI：10.1016/s0040-4020(98)00561-4

  日期：1998.7

  Imidazolo-L-lyxo-piperidinose 4 was synthesised from the D-galactose derivative 8 by two reaction sequences via removal of a terminal carbon atom stepwise incorporation of an imidazole moiety, and eventually intramolecular S(N)2 reaction to the corresponding piperidine ring. Piperidinose 4 proved to be a poor glycosidase inhibitor. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Selective 1,2-syn alkynylation of an open chain sugar: the prominent role of zinc chloride addition
  作者：Stéphane Guillarme、Arnaud Haudrechy

  DOI：10.1016/j.tetlet.2005.03.061

  日期：2005.5

  Depending on the metal, solvent and protective groups, functionalized aldehydes may react through either Felkin or chelated transition states leading to the Felkin Anh product or the 1,2-anti Felkin-Anh product. respectively. Zinc chloride addition proved to be a key aspect in order to favor 1,2-syn nucleophilic attack. (c) 2005 Elsevier Ltd. All rights reserved.