(5R,7R,8R,9R)-7,8,9-trihydroxy-8,9-O-isopropylidene-2,2-dimethyl-1,3-dioxaspiro-<4,5>-decane | 164201-10-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (5R,7R,8R,9R)-7,8,9-trihydroxy-8,9-O-isopropylidene-2,2-dimethyl-1,3-dioxaspiro-<4,5>-decane
• 英文别名: (3'aS,4R,4'R,7'aR)-2,2,2',2'-tetramethylspiro[1,3-dioxolane-4,6'-4,5,7,7a-tetrahydro-3aH-1,3-benzodioxole]-4'-ol
• CAS: 164201-10-9
• 化学式: C₁₃H₂₂O₅
• 分子量: 258.315
• InChiKey: NXWAEIAZOUDWKT-ORXSELOVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  18
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5R,7R,8R,9R)-7,8,9-trihydroxy-8,9-O-isopropylidene-2,2-dimethyl-1,3-dioxaspiro-<4,5>-decane 在 甲醇 、 2,6-二叔丁基-4-甲基吡啶 、 三苯基膦树脂 、 sodium methylate 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 为溶剂， 反应 26.08h， 生成
  参考文献：
  名称：

  Design and synthesis of substrate-mimic inhibitors of mycothiol-S-conjugate amidase from Mycobacterium tuberculosis

  摘要：

  The Staudinger reaction between a polymer-supported triphenylphosphine reagent and pseudo-disaccharide azides is successfully applied to synthesize a variety of substrate-mimic mycothiol analogs. Screening of this new group of analogs against the mycobacterial detoxification enzyme mycothiol-S-conjugate amidase (MCA) yielded several modest inhibitors (IC50 values around 50 mu M) and provided additional structure-activity relationships for future optimization of inhibitors of MCA and its homologs. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2006.10.031
• 作为产物：
  描述：

  3,4-isopropylidenequinide 在 sodium tetrahydroborate 、 对甲苯磺酸 作用下， 以 乙醇 为溶剂， 生成 (5R,7R,8R,9R)-7,8,9-trihydroxy-8,9-O-isopropylidene-2,2-dimethyl-1,3-dioxaspiro-<4,5>-decane
  参考文献：
  名称：

  Design and synthesis of substrate-mimic inhibitors of mycothiol-S-conjugate amidase from Mycobacterium tuberculosis

  摘要：

  The Staudinger reaction between a polymer-supported triphenylphosphine reagent and pseudo-disaccharide azides is successfully applied to synthesize a variety of substrate-mimic mycothiol analogs. Screening of this new group of analogs against the mycobacterial detoxification enzyme mycothiol-S-conjugate amidase (MCA) yielded several modest inhibitors (IC50 values around 50 mu M) and provided additional structure-activity relationships for future optimization of inhibitors of MCA and its homologs. (c) 2006 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2006.10.031

文献信息

• Asymmetric Epoxidation by Chiral Ketones Derived from Carbocyclic Analogues of Fructose
  作者：Zhi-Xian Wang、Susie M. Miller、Oren P. Anderson、Yian Shi

  DOI：10.1021/jo001343i

  日期：2001.1.1

  A number of carbocyclic analogues of the fructose-derived ketone 1 have been prepared and investigated for asymmetric epoxidation. The studies show that the oxygen atom of the pyranose ring of 1 has an impact on the catalyst's activity and selectivity. Conformational, electronic, and steric effects are discussed.

  已经制备了果糖衍生的酮1的许多碳环类似物，并进行了不对称环氧化的研究。研究表明，吡喃糖环1的氧原子对催化剂的活性和选择性有影响。讨论了构象效应，电子效应和空间效应。
• Asymmetric epoxidation of olefins by chiral dioxiranes generated in situ from ketones of d-(−)-quinic acid
  作者：Waldemar Adam、Chantu R. Saha-Möller、Cong-Gui Zhao

  DOI：10.1016/s0957-4166(99)00250-5

  日期：1999.7

  The in situ generated dioxiranes (Caroate as peroxide source) of the optically active ketones 4a and 4b, which may be conveniently prepared from d-(−)-quinic acid, serve as effective oxidants for the asymmetric epoxidation (ee values up to ca. 90% with 4a) of prochiral olefins.

  光学活性酮4a和4b的原位生成的二恶英酮（Caroate作为过氧化物源），其可以方便地由d-（-）-奎尼酸制备，用作不对称环氧化的有效氧化剂（ee值高达约3。 90％含4a）前手性烯烃。
• Alternative Synthesis of (-)-Malyngolide Utilizing (-)-Quinic Acid
  作者：Keizo Matsuo、Takuya Matsumoto、Keiji Nishiwaki

  DOI：10.3987/com-98-8170

  日期：——

  (-)-Malyngolide, an antibiotic isolated from a blue-green algae, was synthesized starting from (-)-quinic acid.

  (-)-Malyngolide是一种从蓝绿藻中分离出的抗生素，它是以(-)-奎尼酸为起始原料进行合成的。
• Transformations of Quinic Acid. Asymmetric Synthesis and Absolute Configuration of Mycosporin I and Mycosporin-gly
  作者：James D. White、Janice H. Cammack、Kazuhiko Sakuma、Gordon W. Rewcastle、Rexford K. Widener

  DOI：10.1021/jo00117a008

  日期：1995.6

  D-(-)-Quinic acid (1) was converted to the fungal metabolites mycosporin I (2) and mycosporin-gly (13) via the iminophosphorane 64. The latter was prepared in 10 steps from 1 using oxidative bromination of quinide 33 to furnish 41. Reduction of the gamma-lactone, followed by protection of the 1,2-diol, was accompanied by migration of the benzoyl group to yield 43. The latter was oxidized to 47 which underwent displacement by sulfinate to give 59. O-Methylation, followed by reduction of the benzoate, afforded 61. Oxidation of 61 produced 62 which was converted to beta-azido enone 63. Treatment of 63 with triphenylphosphine gave crystalline 64. An aza-Wittig reaction of 64 with glyoxylate and reduction of the resultant imine yielded 68 which, after deprotection, afforded 13. Analogous coupling of 64 with diethyl ketomalonate and subsequent reduction of the ester groups led to 2. Mycosporin I and mycosporin-gly are shown by this sequence to possess S absolute configuration.