(2S,6S,7S,10R)-7-isopropyl-10-methyl-2-<(4-methylbenzenesulfonyl)oxy>-1,5-dioxaspiro<5,5>undecane | 138603-01-7

• 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: (2S,6S,7S,10R)-7-isopropyl-10-methyl-2-<(4-methylbenzenesulfonyl)oxy>-1,5-dioxaspiro<5,5>undecane
• 英文别名: 2-((2S,6S,7S,10R)-7-isopropyl-10-methyl-1,5-dioxaspiro[5.5]undecan-2-yl)ethyl 4-methylbenzenesulfonate；2-[(4S,6S,8R,11S)-8-methyl-11-propan-2-yl-1,5-dioxaspiro[5.5]undecan-4-yl]ethyl 4-methylbenzenesulfonate
• CAS: 138603-01-7
• 化学式: C₂₂H₃₄O₅S
• 分子量: 410.575
• InChiKey: LLOJBTUDQFLTTA-WAGURGNTSA-N

物化性质

• 沸点：
  525.2±30.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.73
• 拓扑面积：
  70.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,6S,7S,10R)-7-isopropyl-10-methyl-2-<(4-methylbenzenesulfonyl)oxy>-1,5-dioxaspiro<5,5>undecane 在 咪唑 、 盐酸 、 4-二甲氨基吡啶 、 lithium aluminium tetrahydride 、 正丁基锂 、 草酰氯 、 三氟化硼乙醚 、 氢氟酸 、 四丁基氟化铵 、 碘 、 4-甲基苯磺酸吡啶 、 silica gel 、 sodium hydride 、 二甲基亚砜 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 N,N-二异丙基乙胺 、 sodium iodide 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 二乙二醇二甲醚 、 水 、 N,N-二甲基甲酰胺 、 丙酮 、 乙腈 为溶剂， 反应 262.5h， 生成
  参考文献：
  名称：

  Total Synthesis of Dolatrienoic Acid:  A Subunit of Dolastatin 14

  摘要：

  The (7R,15R)- and (7S,15R)-diastereomers of dolatrienoic acid were synthesized using a convergent strategy. Fragment C5-C9 was obtained through enantiodifferentiation of racemic pentane-1,3,5-triol as the key step, fixing the chirality at C7 of fragments 4 and ent-4. The chirality at C15 of the fragment C10-C16 was introduced from L-glutamic acid. Coupling of these two fragments led to the aldehydes (7R,15R)- and (7S,15R)-2 which were homologated by Horner-Wadsworth-Emmons condensation to give (7R,15R)- and (7S,15R)-dolatrienoic acids.

  DOI：

  10.1021/jo962217a
• 作为产物：
  描述：

  (-)-薄荷酮 在 4-二甲氨基吡啶 、 sodium hydroxide 、 对甲苯磺酸 、 原甲酸三甲酯 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 (2S,6S,7S,10R)-7-isopropyl-10-methyl-2-<(4-methylbenzenesulfonyl)oxy>-1,5-dioxaspiro<5,5>undecane
  参考文献：
  名称：

  Total Synthesis of Dolatrienoic Acid:  A Subunit of Dolastatin 14

  摘要：

  The (7R,15R)- and (7S,15R)-diastereomers of dolatrienoic acid were synthesized using a convergent strategy. Fragment C5-C9 was obtained through enantiodifferentiation of racemic pentane-1,3,5-triol as the key step, fixing the chirality at C7 of fragments 4 and ent-4. The chirality at C15 of the fragment C10-C16 was introduced from L-glutamic acid. Coupling of these two fragments led to the aldehydes (7R,15R)- and (7S,15R)-2 which were homologated by Horner-Wadsworth-Emmons condensation to give (7R,15R)- and (7S,15R)-dolatrienoic acids.

  DOI：

  10.1021/jo962217a

文献信息

• Total Synthesis of (−)‐5‐Deoxyenterocin and Attempted Late‐Stage Functionalization Reactions
  作者：Lilla Koser、Thorsten Bach

  DOI：10.1002/chem.202301996

  日期：2023.10.13

  The polyketide natural product (−)-5-deoxyenterocin (2) was stereoselectively synthesized from aldehyde 1, which was in turn obtained from pentane-1,3,5-triol and (−)-menthone. An attempted functionalization at position C5 remained futile, although several C−H activation methods could be successfully applied to (3aR)-(+)-sclareolide (3).

  聚酮化合物天然产物(-)-5-脱氧肠素( 2 )是由醛1立体选择性合成的，醛1又由戊烷-1,3,5-三醇和(-)-薄荷酮获得。尽管几种 C−H 激活方法可以成功应用于 (3a R )-(+)-香紫苏内酯 ( 3 )，但在 C5 位点的功能化尝试仍然徒劳。
• Synthesis and anti-tubercular activity of 2-nitroimidazooxazines with modification at the C-7 position as PA-824 analogs
  作者：Young-Goo Kang、Chan-Yong Park、Hongsuk Shin、Ramandeep Singh、Garima Arora、Chan-mo Yu、Ill Young Lee

  DOI：10.1016/j.bmcl.2015.06.060

  日期：2015.9

  Tuberculosis (TB) is a major global health problem, and new drug targets and scaffolds need to be identified to combat the emergence of drug resistant TB.The nitroimidazooxazine PA-824 represents a new class of bio-reductive drug to treat TB. In this study we report a 2-nitroimidazooxazine derivative with modification at the C-7 position that exhibited better activity than PA-824 against Mycobacterium tuberculosis (Mtb) H37Rv strain in vitro. From 7a as a key intermediate, we functionalized with benzyl ether (8), phenyl ether (9), benzyl carbonate (10) and benzyl carbamate (11). Among the 23 compounds produced, 8a-R (MIC = 0.078 mu M) with trifluoromethoxy benzyl group was 5-fold more potent than PA-824 (MIC = 0.390 mu M) in the in vitro assays against the wild-type Mtb, and the phenyl ether compound 9g-R (MIC = 0.050 mu M) exhibited the most potent antimycobacterial activity. (C) 2015 Elsevier Ltd. All rights reserved.
• Stereoselective acetalization of 1,3-alkanediols by l-menthone: application to the resolution of racemic 1,3-alkanediols and to the determination of the absolute configuration of enantiomeric 1,3-alkanediols
  作者：Toshiro Harada、Hideaki Kurokawa、Yasuhiro Kagamihara、Sachi Tanaka、Atsushi Inoue、Akira Oku

  DOI：10.1021/jo00031a019

  日期：1992.2

  A general and reliable method for the resolution of racemic 1,3-alkanediols, which involves their conversion into diastereomeric spiroacetals derived from l-menthone, is described. Thus, the reaction of the bis-O-trimethylsilyl derivatives of racemic 1,3-alkanediols with l-menthone in the presence of a catalytic amount of trimethylsilyl trifluoromethanesulfonate affords the diastereomeric spiroacetals 3 and 4. The two can be readily separated by silica gel column chromatography. Hydrolysis of each diastereomer under acidic conditions liberates the corresponding enantiomerically pure diol. An empirically derived correlation of configuration and H-1 NMR chemical shifts for spiroacetals 3 and 4 has been developed which is rationalized based on long-range effects due to the magnetic anisotropy inherent to the menthane ring in a rigid spiroacetal conformation. The method described here should be widely applicable to the determination of the absolute configuration of various 1,3-alkanediols.
• Total Synthesis of Dolatrienoic Acid:  A Subunit of Dolastatin 14
  作者：Sylvie Mouné,、Gilles Niel、Magali Busquet、Ian Eggleston、Patrick Jouin

  DOI：10.1021/jo962217a

  日期：1997.5.1

  The (7R,15R)- and (7S,15R)-diastereomers of dolatrienoic acid were synthesized using a convergent strategy. Fragment C5-C9 was obtained through enantiodifferentiation of racemic pentane-1,3,5-triol as the key step, fixing the chirality at C7 of fragments 4 and ent-4. The chirality at C15 of the fragment C10-C16 was introduced from L-glutamic acid. Coupling of these two fragments led to the aldehydes (7R,15R)- and (7S,15R)-2 which were homologated by Horner-Wadsworth-Emmons condensation to give (7R,15R)- and (7S,15R)-dolatrienoic acids.