methyl (Z)-3-{(4S,5R)-5-[(1R)-1-hydroxy-2-(trityloxy)ethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-propenoate | 122059-90-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: methyl (Z)-3-{(4S,5R)-5-[(1R)-1-hydroxy-2-(trityloxy)ethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-propenoate
• 英文别名: methyl Z-2,3-dideoxy-4,5-O-isopropylidene-7-O-trityl-D-ribo-2-heptenonate；methyl (Z)-3-[(4S,5R)-5-[(1R)-1-hydroxy-2-trityloxyethyl]-2,2-dimethyl-1,3-dioxolan-4-yl]prop-2-enoate
• CAS: 122059-90-9
• 化学式: C₃₀H₃₂O₆
• 分子量: 488.58
• InChiKey: BFUSXTHYVHIWBB-OJZJNMKPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  36
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  74.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  methyl (Z)-3-{(4S,5R)-5-[(1R)-1-hydroxy-2-(trityloxy)ethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-propenoate 生成 methyl (2S)-2-[(3aR,4R,6R,6aR)-2,2-dimethyl-6-(trityloxymethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-2-iodoacetate
  参考文献：
  名称：

  LOPEZ, HERRERA F. J.;PINO, GONZALEZ M. S.;NIETO, SAMPEDRO M.;DOMINGUEZ, A+, TETRAHEDRON, 45,(1988) N 1, C. 269-276

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3-异亚丙氧基-D-呋喃核糖苷 在 4-二甲氨基吡啶 、 三乙胺 、 苯甲酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 42.0h， 生成 methyl (Z)-3-{(4S,5R)-5-[(1R)-1-hydroxy-2-(trityloxy)ethyl]-2,2-dimethyl-1,3-dioxolan-4-yl}-2-propenoate
  参考文献：
  名称：

  Synthesis of enantiomerically pure hydroxylated pyrroline N-oxides from d-ribose

  摘要：

  A convenient way to obtain enantiomerically pure hydroxylated pyrroline N-oxides is reported. The key step is the formation of omega-oxo criciates from (D)-ribose and a subsequent 1,3-azaprotio cyclotransfer reaction of the resulting oximino alkenoate derivatives. The stereochemistry of the nitrones obtained is discussed in relation to that of the starting compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2006.02.006

文献信息

• Stereoselectivity in the formation of unsaturated wittig products and stereospecificity in their electrophile induced cyclization to c-glycosides
  作者：F.J.Lopez Herrera、M.S.Pino Gonzalez、M.Nieto Sampedro、R.M.Dominguez Aciego

  DOI：10.1016/0040-4020(89)80054-7

  日期：1989.1

  The stereoselective synthesis of and unsaturated Wittig products derivated from 2,3--isopropylidene-5--trityl--ribofuranose (3) and 2,3:5,6-di--isopropylidene--mannofuranose (4) was described, as well as their stereo-specific cyclization induced by iodine, to C-glycosides. The absolute configurations at the anomeric center and at the C-α of the aglycone rest, were established by chemical and spectroscopic

  描述了衍生自2,3--异亚丙基-5--三苯甲基-核呋喃糖（3）和2,3：5,6-二-异亚丙基-甘露呋喃糖（4）的立体选择性合成和不饱和Wittig产物。以及碘诱导的立体特异性环化反应生成C-糖苷。通过化学和光谱学方法确定了糖苷配基的异头中心和C-α的绝对构型。
• LOPEZ, HERRERA F. J.;PINO, GONZALEZ M. S.;NIETO, SAMPEDRO M.;DOMINGUEZ, A+, TETRAHEDRON, 45,(1988) N 1, C. 269-276
  作者：LOPEZ, HERRERA F. J.、PINO, GONZALEZ M. S.、NIETO, SAMPEDRO M.、DOMINGUEZ, A+

  DOI：——

  日期：——
• Synthesis of enantiomerically pure hydroxylated pyrroline N-oxides from d-ribose
  作者：Nikolaos G. Argyropoulos、Theodoros D. Panagiotidis、John K. Gallos

  DOI：10.1016/j.tetasy.2006.02.006

  日期：2006.3

  A convenient way to obtain enantiomerically pure hydroxylated pyrroline N-oxides is reported. The key step is the formation of omega-oxo criciates from (D)-ribose and a subsequent 1,3-azaprotio cyclotransfer reaction of the resulting oximino alkenoate derivatives. The stereochemistry of the nitrones obtained is discussed in relation to that of the starting compounds. (c) 2006 Elsevier Ltd. All rights reserved.