methyl 2,3-O-sulfinyl-5-O-triphenylmethyl-β-D-ribofuranoside | 923600-35-5

• 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 2,3-O-sulfinyl-5-O-triphenylmethyl-β-D-ribofuranoside
• 英文别名: (3aR,4R,6R,6aR)-4-methoxy-6-(trityloxymethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3,2]dioxathiole 2-oxide
• CAS: 923600-35-5
• 化学式: C₂₅H₂₄O₆S
• 分子量: 452.528
• InChiKey: RFQREOQDTMKRJR-FJETXIILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  82.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2,3-O-sulfinyl-5-O-triphenylmethyl-β-D-ribofuranoside 在 吡啶 、 ruthenium trichloride 、 sodium periodate 、 sodium azide 、 硫酸 作用下， 以 1,4-二氧六环 、 四氯化碳 、 六甲基磷酰三胺 、 水 、 乙腈 为溶剂， 反应 93.0h， 生成 (2S,3S,4R,5R)-3-azido-5-methoxy-4-(4-methylphenyl)sulfonyloxyoxolane-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of Optically Pure 3,4-Disubstituted l-Glutamates from a Novel 2,3-Aziridino-γ-lactone 4-Carboxylate Derivative

  摘要：

  The synthesis of the N-acetyl and N-Cbz derivatives of (1S,4S,5R)-4-(methoxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one (24 and 27, respectively) from D-ribose is described. While compound 24 reacted with methanol in the presence of boron trifluoride etherate to give the novel 2,3-iminoglutamate derivative 28, compound 27 afforded, under the same conditions, the 4(S)-hydroxy-3(S)methoxy-L-glutamate 31. Similarly, reaction of 27 with ethanol and benzyl alcohol gave the corresponding 3(S)-ethoxy and 3(S)-(benzyloxy) analogues of 31. This represents the first example of the use of a carbohydrate for the preparation of L-glutamate derivatives as well as the first example of a stereocontrolled synthesis of glutamate analogues dissymmetrically substituted at the beta,gamma-positions.

  DOI：

  10.1021/jo951983z
• 作为产物：
  描述：

  methyl 5-O-trityl-β-D-ribofuranoside 在 氯化亚砜 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 0.75h， 以86%的产率得到methyl 2,3-O-sulfinyl-5-O-triphenylmethyl-β-D-ribofuranoside
  参考文献：
  名称：

  Synthesis of Optically Pure 3,4-Disubstituted l-Glutamates from a Novel 2,3-Aziridino-γ-lactone 4-Carboxylate Derivative

  摘要：

  The synthesis of the N-acetyl and N-Cbz derivatives of (1S,4S,5R)-4-(methoxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one (24 and 27, respectively) from D-ribose is described. While compound 24 reacted with methanol in the presence of boron trifluoride etherate to give the novel 2,3-iminoglutamate derivative 28, compound 27 afforded, under the same conditions, the 4(S)-hydroxy-3(S)methoxy-L-glutamate 31. Similarly, reaction of 27 with ethanol and benzyl alcohol gave the corresponding 3(S)-ethoxy and 3(S)-(benzyloxy) analogues of 31. This represents the first example of the use of a carbohydrate for the preparation of L-glutamate derivatives as well as the first example of a stereocontrolled synthesis of glutamate analogues dissymmetrically substituted at the beta,gamma-positions.

  DOI：

  10.1021/jo951983z

文献信息

• Synthesis and Reactions of Anhydro-Azido-thio-D-lyxofuranosides
  作者：Dirk Otzen、Jürgen Voss、Gunadi Adiwidjaja

  DOI：10.1080/10426500500326545

  日期：2006.7.1

  2,5-anhydro-3-azido-2-thio-D-lyxofuranosides and 3,5-anhydro-2-azido-3-thio-D-lyxofuranosides were prepared from methyl D-xylofuranoside or methyl D-ribofuranoside via corresponding 2,3-epoxysugars or the 5-O-trityl derivative. The sulfur was introduced into molecules by use of the thio-Mitsunobu reaction. Bicyclic azido-thiosugars were transformed into nucleoside analogues, oxidized to sulfoxides and sulfones, and reduced to bicyclic amino-thiosugars. Structures and configurations of products were determined by NMR spectroscopy or X-ray structure analyses.
• Synthesis of Optically Pure 3,4-Disubstituted <scp>l</scp>-Glutamates from a Novel 2,3-Aziridino-γ-lactone 4-Carboxylate Derivative
  作者：Philippe Dauban、Angèle Chiaroni、Claude Riche、Robert H. Dodd

  DOI：10.1021/jo951983z

  日期：1996.1.1

  The synthesis of the N-acetyl and N-Cbz derivatives of (1S,4S,5R)-4-(methoxycarbonyl)-3-oxa-6-azabicyclo[3.1.0]hexan-2-one (24 and 27, respectively) from D-ribose is described. While compound 24 reacted with methanol in the presence of boron trifluoride etherate to give the novel 2,3-iminoglutamate derivative 28, compound 27 afforded, under the same conditions, the 4(S)-hydroxy-3(S)methoxy-L-glutamate 31. Similarly, reaction of 27 with ethanol and benzyl alcohol gave the corresponding 3(S)-ethoxy and 3(S)-(benzyloxy) analogues of 31. This represents the first example of the use of a carbohydrate for the preparation of L-glutamate derivatives as well as the first example of a stereocontrolled synthesis of glutamate analogues dissymmetrically substituted at the beta,gamma-positions.