(3S,4S)-4-azido-3-hydroxy-6-methylheptanoic acid | 55714-49-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羟基酸及其衍生物
• 英文名称: (3S,4S)-4-azido-3-hydroxy-6-methylheptanoic acid
• 英文别名: (3S,4S)-4-Azido-3-hydroxy-6-methylheptansaeure
• CAS: 55714-49-3
• 化学式: C₈H₁₅N₃O₃
• 分子量: 201.225
• InChiKey: HUVBXMOLOCCDRP-BQBZGAKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  14
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  71.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3S,4S)-4-azido-3-hydroxy-6-methylheptanoic acid 在 palladium on activated charcoal 氢气 作用下， 以 溶剂黄146 为溶剂， 40.0 ℃ 、101.32 kPa 条件下， 反应 2.5h， 以85%的产率得到(3S,4S)-(-)-他汀
  参考文献：
  名称：

  Enantioselective Synthesis of Pyrrolydinonyl Thymine Nucleoside Analogues

  摘要：

  描述了从天然苹果酸出发，实现一类新型光学活性核苷类似物的对映选择性合成。在所给的核苷类似物中，四氢呋喃环被一个带有伯醇和仲醇的吡咯烷酮环取代，这可能对制备新型寡核苷酸有用。经测试，制备的核苷类似物对病毒没有活性。

  DOI：

  10.1246/cl.1999.687
• 作为产物：
  描述：

  (2R,3S)-3-azido-1,2-epoxy-5-methylhexane 在 sodium hydroxide 、 双氧水 作用下， 以 甲醇 为溶剂， 生成 (3S,4S)-4-azido-3-hydroxy-6-methylheptanoic acid
  参考文献：
  名称：

  An enantiospecific and versatile synthesis of statine

  摘要：

  A short, enantiospecific synthesis of statine is described, starting from a readily available aldehyde. The control of chirality was effected by using the Sharpless asymmetric epoxidation procedure.

  DOI：

  10.1016/s0957-4166(00)80530-3

文献信息

• Synthesis of (3<i>S</i>, 4<i>S</i>)- and (3<i>S</i>, 4<i>R</i>)-4-Amino-3-hydroxy-6-methylheptanoic Acid, and Their<i>N</i>-(Acetyl-L-valyl-L-valyl) Derivatives
  作者：Mitsuhiro Kinoshita、Akito Hagiwara、Shinpei Aburaki

  DOI：10.1246/bcsj.48.570

  日期：1975.2

  ptanoic acid (10a) present in pepstatins, specific inhibitors of acid proteases, and its (+) (3S,4R) diastereomer (10b) were synthesized starting from 3-deoxy-1,2-O-isopropylidene-α-D-erythro-pentodialdo-1,4-furanose (1) through highly stereoselective and stereospecific routes. The partial pep tide of pepstatin Ac, N-(acetyl-L-valyl-L-valyl)-(3S,4S)-4-amino-3-hydroxy-6-methylheptanoic acid (15a) and

  存在于胃蛋白酶抑制剂、酸性蛋白酶的特异性抑制剂及其 (+) (3S,4R) 非对映异构体 (10b) 中的天然 (-)(3S,4S)-4-氨基-3-羟基-6-inethylheptanoic 酸 (10a) 是从 3-deoxy-1,2-O-isopropylidene-α-D-erythro-pentodialdo-1,4-furanose (1) 通过高度立体选择性和立体特异性路线合成。胃酶抑素Ac、N-(乙酰基-L-缬氨酰-L-缬氨酰)-(3S,4S)-4-氨基-3-羟基-6-甲基庚酸(15a)及其(3S,4R)的部分肽非对映异构体 (15b) 是通过 10a 和 10b 的叔丁酯分别与乙酰基-L-缬氨酰-L-缬氨酸叠氮化物的叠氮偶联合成的。化合物15a抑制胃蛋白酶的蛋白水解，然而，非对映异构体15b对胃蛋白酶没有抑制作用。
• Bertelli, Lucia; Fiaschi, Rita; Napolitano, Elio, Gazzetta Chimica Italiana, 1993, vol. 123, # 9, p. 521 - 524
  作者：Bertelli, Lucia、Fiaschi, Rita、Napolitano, Elio

  DOI：——

  日期：——
• Unusual Regioselection in the Mitsunobu Reactions of <i>s</i><i>yn</i>-2,3-Dihydroxy Esters:  Synthesis of Statine and Its Diastereomer
  作者：Soo Y. Ko

  DOI：10.1021/jo015967f

  日期：2002.4.1

  Mitsunobu reactions of syn-2,3-dihydroxy esters exhibit a complete regioselection for the beta-hydroxyl group. Benzoylation, azidation, and tosylation have been performed under these conditions. beta-Functionalizations of syn-2,3-dihydroxy esters are uncommon, and the Mitsunobu reactions are complementary to other diol chemistries in the regioselection. In addition, the configurational inversion accompanying the Mitsunobu protocol offers a means for diastereochemical diversity, as exemplified by a synthesis of statine and its anti diastereomer. These findings will further expand the synthetic utilities of the Sharpless AD process.
• ABSOLUTE CONFIGURATION OF 4-AMINO-3-HYDROXY-6-METHYLHEPTANOIC ACID PRESENT IN PEPSTATIN A AND STEREOSPECIFIC SYNTHESIS OF ALL FOUR ISOMERS
  作者：MITSUHIRO KINOSHITA、SHIMPEI ABURAKI、AKITO HAGIWARA、JIRO IMAI

  DOI：10.7164/antibiotics.26.249

  日期：——
• YANAGISAWA, HIROAKI;KANAZAKI, TAKURO;NISHI, TAKAHIDE, CHEM. LETT.,(1989) N, C. 687-690
  作者：YANAGISAWA, HIROAKI、KANAZAKI, TAKURO、NISHI, TAKAHIDE

  DOI：——

  日期：——