methyl (1RS)-2,2-((R,R)-cycloheptane-1,2-dioxy)cyclopentanecarboxylate | 206760-76-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1RS)-2,2-((R,R)-cycloheptane-1,2-dioxy)cyclopentanecarboxylate
• 英文别名: methyl (3aR,8aR)-spiro[4,5,6,7,8,8a-hexahydro-3aH-cyclohepta[d][1,3]dioxole-2,2'-cyclopentane]-1'-carboxylate
• CAS: 206760-76-1
• 化学式: C₁₄H₂₂O₄
• 分子量: 254.326
• InChiKey: FUMBTLXQGNUKTH-PQDIPPBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.93
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  methyl (1RS)-2,2-((R,R)-cycloheptane-1,2-dioxy)cyclopentanecarboxylate 以86%的产率得到
  参考文献：
  名称：

  Suemune Hiroshi, Maeda Kazunori, Kato Keisuke, Sakai Kiyoshi, J. Chem. Soc. Perkin Trans. 1, (1994) N 23, S 3441-3447

  摘要：

  DOI：
• 作为产物：
  描述：

  (1R,2R)-1,2-环庚烷二醇 、 2-甲氧羰基环戊酮 在 对甲苯磺酸 作用下， 以 苯 为溶剂， 以98%的产率得到methyl (1RS)-2,2-((R,R)-cycloheptane-1,2-dioxy)cyclopentanecarboxylate
  参考文献：
  名称：

  通过分子内狄尔斯-阿尔德反应的不对称全合成甲萘酚A

  摘要：

  已经实现了具有引人入胜的四环骨架的新型天然产物加勒比烯醇A（1）的全合成。该合成具有分子内Diels–Alder（IMDA）反应，可轻松构建三烯醇A（1）的三环[5–7–6]骨架，并具有仿生氧化反应，可形成2-羟基呋喃-2（5）。H）-加勒比醇A（1）的一个基序作为关键步骤。这种合成方法还表明，底物8中C（2）处的sp 2碳是在7中形成三环[5-7-6]骨架的关键因素。

  DOI：

  10.1021/jo4006156

文献信息

• Stereoselective Synthesis of 4'-.ALPHA.-Alkylcarbovir Derivatives Based on an Asymmetric Synthesis or Chemoenzymatic Procedure.
  作者：Keisuke KATO、Hisaki SUZUKI、Hiromichi TANAKA、Tadashi MIYASAKA、Masanori BABA、Kentaro YAMAGUCHI、Hiroyuki AKITA

  DOI：10.1248/cpb.47.1256

  日期：——

  Stereoselective synthesis of 4'-α-alkylcarbovir derivatives 4 was described based on asymmetric synthesis or a chemoenzymatic procedure. The asymmetric alkylation of chiral acetal 7 gave the alkylated enol ethers 9a-c possessing a chiral quaternary carbon. The key carbocyclic intermediates 14a-c were synthesized from 9a-c via eleven-steps. Coupling of 14a-c with 2-amino-6-chloropurine followed by desilylation and subsequent hydrolysis afforded the target compounds 4a-c in moderate yield. The optically active cyclopentene intermediates 5a-c and 6a-c were also prepared by enzymatic resolution of (±)-5a-c and (±)-6a-c, respectively.

  基于不对称合成或化学酶法过程，描述了 4'-α- 烷基卡巴韦衍生物 4 的立体选择性合成。通过手性缩醛 7 的不对称烷基化，得到了具有手性季碳的烷基化烯醇醚 9a-c。由 9a-c 经过 11 个步骤合成了关键的碳环中间体 14a-c。将 14a-c 与 2-氨基-6-氯嘌呤偶联，然后进行脱硅和水解，就得到了目标化合物 4a-c，收率适中。通过酶解 (±)-5a-c 和 (±)-6a-c 还分别制备出了具有光学活性的环戊烯中间体 5a-c 和 6a-c。
• Asymmetric alkylation using chiral cyclic diols to prepare a quaternary carbon
  作者：Keisuke Kato、Hiroshi Suemune、Kiyoshi Sakai

  DOI：10.1016/s0040-4020(01)87012-5

  日期：1994.3

  Asymmetric alkylation of cyclic and acyclic beta-keto ester acetals (4, 5, 13, 14, and 18) with C-2-symmetric cycloalkane-1,2-dioxy moiety proceeded in a highly diastereoselective manner to afford enol ethers (9-12, 15-17, 19a-c) with a chiral quaternary carbon.
• Enantio- and diastereoselective synthesis of 4′-α-substituted carbocyclic nucleosides
  作者：Keisuke Kato、Hisaki Suzuki、Hiromichi Tanaka、Tadashi Miyasaka

  DOI：10.1016/s0957-4166(98)00065-2

  日期：1998.3

  Enantio-and diastereoselective synthesis of 4-alpha-alkylcarbovir derivatives 5 were achieved based on Sakai's asymmetric alkylation of beta-keto esters. The key carbocyclic intermediate 14 was synthesized from 8 via an eleven-step sequence. Coupling of 14 with 2-amino-6-chloropurine followed by desilylation and subsequent hydrolysis gave the target compounds 5 in moderate yields. (C) 1998 Elsevier Science Ltd. All rights reserved.
• Suemune, Hiroshi; Maeda, Kazunori; Kato, Keisuke, Journal of the Chemical Society. Perkin transactions I, 1994, # 23, p. 3441 - 3448
  作者：Suemune, Hiroshi、Maeda, Kazunori、Kato, Keisuke、Sakai, Kiyoshi

  DOI：——

  日期：——
• Application of chiral cyclic diols to asymmetric alkylation
  作者：Keisuke Kato、Hiroshi Suemune、Koyoshi Sakai

  DOI：10.1016/0040-4039(92)88062-a

  日期：1992.1

  Chiral cyclic (6- or 7-membered ring) diols were found to be excellent chiral auxiliaries for asymmetric alkylation of cyclic (or acyclic) beta-keto esters.