(R)-(+)-3-Hydroxy-3-methyl-5-(benzyloxy)pentanoic acid | 87137-57-3

• 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: (R)-(+)-3-Hydroxy-3-methyl-5-(benzyloxy)pentanoic acid
• 英文别名: (R)-5-benzyloxy-3-hydroxy-3-methylpentanoic acid；(R)-5-O-benzylmevalonic acid；(3R)-3-hydroxy-3-methyl-5-phenylmethoxypentanoic acid
• CAS: 87137-57-3
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: FCSLJUNNFVCCKQ-CYBMUJFWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 可旋转键数：
  7
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (R)-(+)-3-Hydroxy-3-methyl-5-(benzyloxy)pentanoic acid 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 以70%的产率得到D-甲瓦龙酸?酯
  参考文献：
  名称：

  Ohta, Tomihisa; Tabei, Nobuaki; Nozoe, Shigeo, Heterocycles, 1989, vol. 28, # 1, p. 425 - 432

  摘要：

  DOI：
• 作为产物：
  描述：

  (2S,3S)-2,3-环氧香叶醇 在 吡啶 、 sodium tetrahydroborate 、 sodium periodate 、 lithium aluminium tetrahydride 、 jones' reagent 、 双氧水 、 sodium hydride 、 碳酸氢钠 、 臭氧 、 间氯过氧苯甲酸 、 Na(PhSe)BH₃ 作用下， 以 正己烷 、 水 、 丙酮 为溶剂， 反应 48.0h， 生成 (R)-(+)-3-Hydroxy-3-methyl-5-(benzyloxy)pentanoic acid
  参考文献：
  名称：

  Ohta, Tomihisa; Tabei, Nobuaki; Nozoe, Shigeo, Heterocycles, 1989, vol. 28, # 1, p. 425 - 432

  摘要：

  DOI：

文献信息

• Chirality of the 3-Hydroxy-3-methylglutaric Acid Moiety of Fasciculic Acid A, a Calmodulin Antagonist Isolated from Naematoloma fasciculare.
  作者：Shigeo NOZOE、Akira TAKAHASHI、Tomihisa OHTA

  DOI：10.1248/cpb.41.1738

  日期：——

  The chirality of the 3-hydroxy-3-methylglutaric acid (HMGA) moiety of fasciculic acid A (1), a calmodulin antagonist isolated from Naematoloma fasciculare, was established to be S by comparing the 1H-NMR spectrum of the L-alanylamide of HMGA derived from 1 with those of its diastereomer and the diastereomeric mixture.

  通过比较从筋膜瘤（Naematoloma fasciculare）中分离出的钙调素拮抗剂筋膜瘤酸甲（1）中 HMGA 的 L-丙氨酰酰胺的 1H-NMR 光谱及其非对映异构体和非对映异构体混合物的 1H-NMR 光谱，确定了筋膜瘤酸甲（1）的 3-羟基-3-甲基戊二酸（HMGA）分子的手性为 S。
• Enantioselective Synthesis of 2-Methyl-2-hydroxy-.gamma.-butyrolactone and Its Application in the Asymmetric Synthesis of Frontalin and Mevalonolactone
  作者：Franklin A. Davis、G. Venkat Reddy、Bang-Chi Chen、Anil Kumar、M. Serajul Haque

  DOI：10.1021/jo00124a030

  日期：1995.9

  The asymmetric hydroxylation of the enolates of fully substituted acyclic ester 8 and lactone 10 with (camphorylsulfonyl)oxaziridines 1a-c was studied. The stereoselectivities of the tertiary alpha-hydroxy carbonyl products were highly dependent on the enolate structure, the oxidizing reagents, and the reaction conditions. While high diastereoselectivity (up to 94%) was obtained for enolates of fully substituted menthol ester 8 with substoichiometric amounts of oxaziridine 1a, the yields were unsatisfactory. On the other hand, the enantioselective alpha-hydroxylation of the sodium enolate of 2-methyl-gamma-butyrolactone (10) with [(8,8-dimethoxycamphoryl)sulfonyl]oxaziridine (1c) afforded alpha-hydroxy lactone 11a in 70% yield and 84% ee. The enantiomeric excess was improved to > 93% ee by crystallization of the corresponding benzoyl ester 11c. The utility of both enantiomers of 11c were demonstrated in the formal asymmetric syntheses of the pheromone, (1S,5R)-(-)-frontalin (13) and in the asymmetric synthesis of (R)-(-)-mevalonolactone (20).
• WILSON, W. K.;BACA, S. B.;BARBER, Y. J.;SCALLEN, T. J.;MORROW, C. J., J. ORG. CHEM., 1983, 48, N 22, 3960-3966
  作者：WILSON, W. K.、BACA, S. B.、BARBER, Y. J.、SCALLEN, T. J.、MORROW, C. J.

  DOI：——

  日期：——