(4S,5R)-2,2-dimethyl-4-(2-methylpropan-1-yl)-5-<(1S)-1--2-cyclohexylethyl>-1,3-dioxolane | 143285-53-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (4S,5R)-2,2-dimethyl-4-(2-methylpropan-1-yl)-5-<(1S)-1--2-cyclohexylethyl>-1,3-dioxolane
• 英文别名: tert-butyl N-[(1S)-2-cyclohexyl-1-[(4R,5S)-2,2-dimethyl-5-(2-methylpropyl)-1,3-dioxolan-4-yl]ethyl]carbamate
• CAS: 143285-53-4
• 化学式: C₂₂H₄₁NO₄
• 分子量: 383.572
• InChiKey: IAFCMARQPSWXME-GBESFXJTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  56.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5R)-2,2-dimethyl-4-(2-methylpropan-1-yl)-5-<(1S)-1--2-cyclohexylethyl>-1,3-dioxolane 在 水 、 三氟乙酸 作用下， 生成 (2S,3R,4S)-2-amino-1-cyclohexyl-3,4-dihydroxy-6-methylheptane
  参考文献：
  名称：

  从D-核糖合成肾素抑制剂的二羟乙烯二肽等排物的多用途和立体定向合成

  摘要：

  从D-核糖立体定向合成了（2 S，3 R，4 S）-2-氨基-1-环己基-6-甲基庚烷-3,4-二醇，一种用于肾素抑制剂的二羟基亚乙基二肽等排体。该方法可以很容易地适应于其他二羟基亚乙基等排体

  DOI：

  10.1016/s0040-4039(00)92504-8
• 作为产物：
  描述：

  环己氯化镁 在 palladium on activated charcoal 、 copper(l) iodide 叠氮磷酸二苯酯 、 氢气 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 43.0h， 生成 (4S,5R)-2,2-dimethyl-4-(2-methylpropan-1-yl)-5-<(1S)-1--2-cyclohexylethyl>-1,3-dioxolane
  参考文献：
  名称：

  从D-核糖合成肾素抑制剂的二羟乙烯二肽等排物的多用途和立体定向合成

  摘要：

  从D-核糖立体定向合成了（2 S，3 R，4 S）-2-氨基-1-环己基-6-甲基庚烷-3,4-二醇，一种用于肾素抑制剂的二羟基亚乙基二肽等排体。该方法可以很容易地适应于其他二羟基亚乙基等排体

  DOI：

  10.1016/s0040-4039(00)92504-8

文献信息

• Dipeptide isosteres. 1. Synthesis of dihydroxyethylene dipeptide isosteres via diastereoselective additions of alkyllithium reagents to N,N-dimethylhydrazones. Preparation of renin and HIV-1 protease inhibitor transition-state mimics
  作者：William R. Baker、Stephen L. Condon

  DOI：10.1021/jo00064a013

  日期：1993.6

  The amino and diamino dihydroxyethylene dipeptide isosteres 19a,b and 23 are important intermediates for the preparation of inhibitors of human renin and HIV-1 protease, respectively. A general synthetic strategy was developed to access both dipeptide isosteres. The key step was a diastereoselective addition of an alkyllithium reagent to an aldehyde hydrazone. Thus, isosteres 19a and 19b were synthesized by addition of either benzyllithium or (cyclohexylmethyl)lithium to (4S,5R)-2,2-dimethyl-4-(2-methylpropan-1-yl)-5-formyl-1,3-dioxolane N,N-dimethylhydrazone (4) in diethyl ether at -10-degrees-C. The hydrazine addition product was reduced to the amine, and the acetonide protecting group was removed. The resulting amino diol was derivatized as either a N-Boc analogue or coupled to N-(tert-butyloxycarbonyl)-3-(thiazol-4-yl)alanine. The addition reactions were completely diastereoselective, affording only the chelation-controlled products (beta attack, S configuration at C(2)). Hydrazone 4 was prepared from either D-isoascorbic acid (1), divinyl carbinol (5), or chlorobenzene (9). Application of the hydrazone/alkyllithium reaction to the synthesis of the diamino dihydroxyethylene dipeptide isostere 23 was also achieved. Reaction of the bis-hydrazone 22 with benyllithium, followed by Raney nickel reduction of the hydrazine addition product, formation of the bis-benzyl carbamate, and deprotection of the acetonide with methanolic HCI gave the diamino dihydroxyethylene dipeptide isostere 23 in 36 % overall yield (four steps). Isostere 23 is an intermediate useful for the preparation Of C2 symmetric HIV-1 protease inhibitors.
• A versatile and stereospecific synthesis of a dihydroxyethylene Dipeptide Isostere of Renin inhibitors from D-ribose
  作者：Ming Fai Chan、Chi-Nung Hsiao

  DOI：10.1016/s0040-4039(00)92504-8

  日期：1992.6

  (2S, 3R, 4S)-2-amino-1-cyclohexyl-6-methylheptane-3,4-diol, a dihydroxythylene dipeptide isostere for renin inhibitors, was synthesized from D-ribose stereospecifically. This method can be readily adapted to other dihydroxythylene isosteres

  从D-核糖立体定向合成了（2 S，3 R，4 S）-2-氨基-1-环己基-6-甲基庚烷-3,4-二醇，一种用于肾素抑制剂的二羟基亚乙基二肽等排体。该方法可以很容易地适应于其他二羟基亚乙基等排体