(2R,3R,4R)-3,4-bis-benzyloxy-2-methanesulfonyloxymethyl-piperidine-1-carboxylic acid benzyl ester | 1430588-23-0

• 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,3R,4R)-3,4-bis-benzyloxy-2-methanesulfonyloxymethyl-piperidine-1-carboxylic acid benzyl ester
• CAS: 1430588-23-0
• 化学式: C₂₉H₃₃NO₇S
• 分子量: 539.65
• InChiKey: DJHUAJFMCBDOJV-JCYYIGJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.54
• 重原子数：
  38.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  91.37
• 氢给体数：
  0.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  benzyl (3R,4R,5R)-4,5-bis(benzyloxy)-7-bromo-1-phenylhept-1-en-3-ylcarbamate 在 sodium tetrahydroborate 、 potassium tert-butylate 、 臭氧 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 (2R,3R,4R)-3,4-bis-benzyloxy-2-methanesulfonyloxymethyl-piperidine-1-carboxylic acid benzyl ester
  参考文献：
  名称：

  Total synthesis of d-fagomine and 6-deoxyfagomine

  摘要：

  Total synthesis of D-fagomine and 6-deoxyfagomine from readily available D-lyxose is described. The key steps included regioselective and diastereoselective amination, hydroboration-oxidation, and Appel reaction. The reaction of 3,4-anti-tribenzyl ether with chlorosulfonyl isocyanate in toluene at 0 degrees C afforded 3,4-anti-amino alcohol, an essential compound for the preparation of D-fagomine and 6-deoxyfagomine, with a high diastereoselectivity (dr=26:1) in 74% yield. The origin of diastereoselectivity can be explained by the neighboring group effect, which leads to retention of the stereochemistry. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.03.046