(1S,2R)-2-((tert-butyldiphenylsiloxy)methyl)-1-[((R)-tert-butylsulfinyl)iminomethyl]cyclopropane | 1338719-67-7

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: (1S,2R)-2-((tert-butyldiphenylsiloxy)methyl)-1-[((R)-tert-butylsulfinyl)iminomethyl]cyclopropane
• CAS: 1338719-67-7
• 化学式: C₂₅H₃₅NO₂SSi
• 分子量: 441.71
• InChiKey: WHAAEQRUXNEXDA-HNMNOHOESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.73
• 重原子数：
  30.0
• 可旋转键数：
  7.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  38.66
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  (1S,2R)-2-((tert-butyldiphenylsiloxy)methyl)-1-[((R)-tert-butylsulfinyl)iminomethyl]cyclopropane 在 盐酸 、 potassium permanganate 、 sodium periodate 、 偶氮二甲酸二异丙酯 、 水 、 碳酸氢钠 、 sodium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 、 乙酸乙酯 、 丙酮 、 甲苯 为溶剂， 反应 17.5h， 生成 (3S,4R)-3,4-methano-Nα,Nδ,Nω-tri-Cbz-D-arginine
  参考文献：
  名称：

  Synthesis of a series of 3,4-methanoarginines as side-chain conformationally restricted analogues of arginine

  摘要：

  A series of optically active stereoisomers of 3,4-methanoarginine (1-4 and ent-1-ent-4) with trans/cis, D/L, and syn/anti stereochemical diversity, the side-chains of which were restricted in various special arrangements, was designed as biologically useful arginine mimetics. These conformationally restricted arginine analogues were synthesized effectively by using a series of chiral 3,4-methanoamino acid equivalents (7-10 and ent-7-ent-10) as the key synthetic units. Their biological evaluation with three isoforms of nitric oxide synthase showed that trans-3,4-methano-L-syn-arginine (2) was a good substrate, having close potency to L-arginine, and isoforms selectivities were also similar to those of L-arginine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.049
• 作为产物：
  描述：

  (R)-(+)-叔丁基亚磺酰胺 、 (1S,2R)-2-(((叔丁基二苯基硅烷基)氧基)甲基)环丙烷-1-甲醛 在 copper(II) sulfate 作用下， 以 二氯甲烷 为溶剂， 以99%的产率得到(1S,2R)-2-((tert-butyldiphenylsiloxy)methyl)-1-[((R)-tert-butylsulfinyl)iminomethyl]cyclopropane
  参考文献：
  名称：

  Synthesis of a series of 3,4-methanoarginines as side-chain conformationally restricted analogues of arginine

  摘要：

  A series of optically active stereoisomers of 3,4-methanoarginine (1-4 and ent-1-ent-4) with trans/cis, D/L, and syn/anti stereochemical diversity, the side-chains of which were restricted in various special arrangements, was designed as biologically useful arginine mimetics. These conformationally restricted arginine analogues were synthesized effectively by using a series of chiral 3,4-methanoamino acid equivalents (7-10 and ent-7-ent-10) as the key synthetic units. Their biological evaluation with three isoforms of nitric oxide synthase showed that trans-3,4-methano-L-syn-arginine (2) was a good substrate, having close potency to L-arginine, and isoforms selectivities were also similar to those of L-arginine. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.049