6-O-[6-O-benzyl-2,3,4-trideoxy-4-N-(mesylamino)-α-D-erythro-hex-2-enopyranosyl]-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 6-O-[6-O-benzyl-2,3,4-trideoxy-4-N-(mesylamino)-α-D-erythro-hex-2-enopyranosyl]-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• 英文别名: N-[(2S,3S,6S)-2-(phenylmethoxymethyl)-6-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]-3,6-dihydro-2H-pyran-3-yl]methanesulfonamide
• 化学式: C₂₆H₃₇NO₁₀S
• 分子量: 555.646
• InChiKey: MSKVXMUILUMFKT-RWQFOSOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  38
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  128
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  6-O-benzyl-3-deoxy-3-azido-D-gulal 在 吡啶 、 potassium tert-butylate 、 苯硫酚 、 三乙胺 、 tin(ll) chloride 作用下， 以 乙腈 、 苯 为溶剂， 反应 12.5h， 生成 6-O-[6-O-benzyl-2,3,4-trideoxy-4-N-(mesylamino)-α-D-erythro-hex-2-enopyranosyl]-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Stereoselective Synthesis of 4-(N-Mesylamino)-2,3-unsaturated- α-O-glycosides via a New Glycal-Derived Vinyl α-N-(Mesyl)-aziridine

  摘要：

  N-Mesyl aziridine 7 alpha(1) a new activated vinyl aziridine derived from D-glucal, has been synthesized by cyclization of trans-NO-dimesylate 6 with t-BuOK in anhydrous benzene. The reaction of 7 alpha with alcohols, phenol, and monosaccharides (O-nucleophiles) leads to the corresponding 4-N(mesylam ino)-2,3-unsaturated-aglycos ides and disaccharides through a completely regioselective 1,4-addition process that proceeds with high or complete alpha-stereoselectivity.

  DOI：

  10.1021/ol050053r

文献信息

• Stereoselective Synthesis of 4-(<i>N</i>-Mesylamino)-2,3-unsaturated- α-<i>O</i>-glycosides via a New Glycal-Derived Vinyl α<i>-N</i>-(Mesyl)-aziridine
  作者：Valeria Di Bussolo、Maria Rosaria Romano、Mauro Pineschi、Paolo Crotti

  DOI：10.1021/ol050053r

  日期：2005.3.1

  N-Mesyl aziridine 7 alpha(1) a new activated vinyl aziridine derived from D-glucal, has been synthesized by cyclization of trans-NO-dimesylate 6 with t-BuOK in anhydrous benzene. The reaction of 7 alpha with alcohols, phenol, and monosaccharides (O-nucleophiles) leads to the corresponding 4-N(mesylam ino)-2,3-unsaturated-aglycos ides and disaccharides through a completely regioselective 1,4-addition process that proceeds with high or complete alpha-stereoselectivity.