(2S,3R,4R)-2,3-isopropylidenedioxy-4-methoxybutyrolactone | 125851-01-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,4R)-2,3-isopropylidenedioxy-4-methoxybutyrolactone
• 英文别名: (1R,5S,8R)-8-methoxy-3,3-dimethyl-2,4,7-trioxabicyclo(3.3.0)octan-6-one；(3aS,6R,6aR)-6-methoxy-2,2-dimethyldihydrofuro[3,4-d][1,3]dioxol-4(3aH)-one；(3aS,6R,6aR)-6-methoxy-2,2-dimethyl-6,6a-dihydro-3aH-furo[3,4-d][1,3]dioxol-4-one
• CAS: 125851-01-6
• 化学式: C₈H₁₂O₅
• 分子量: 188.18
• InChiKey: BXFYHFZSSWKNFZ-HBPOCXIASA-N

物化性质

• 溶解度：
  可溶于氯仿、甲醇

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3R,4R)-2,3-isopropylidenedioxy-4-methoxybutyrolactone 在 正丁基锂 、 palladium on activated charcoal 、 氢气 、 sodium hydride 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 5.67h， 生成 (3aR,6aS)-tert-butyl 2-(2,2-dimethyltetrahydro-4H-cyclopenta[d][1,3]-dioxol-4-ylidene)acetate
  参考文献：
  名称：

  氯吡格雷具有生物活性的哌啶代谢物的合成：结构测定和分析物开发

  摘要：

  氯吡格雷是具有活性代谢产物的前药抗凝剂，其不可逆地抑制血小板表面GPCR P2Y 12并因此抑制血小板活化。然而，由于对代谢物活性和立体化学的不精确了解，以及缺乏用于量化体内代谢物形成的可接受分析物，对患者反应的了解受到了限制。公开了用于产生氯吡格雷的所有生物活性代谢物，其立体化学分配以及通过三种概念上正交的途径开发稳定的分析物的方法。

  DOI：

  10.1021/acs.joc.5b00632
• 作为产物：
  描述：

  Methyl 2,3-O-isopropylidene-5-aldehydo-β-D-ribofuranoside 在 potassium permanganate 、 copper(II) sulfate 作用下， 以 苯 为溶剂， 反应 20.0h， 生成 (2S,3R,4R)-2,3-isopropylidenedioxy-4-methoxybutyrolactone
  参考文献：
  名称：

  An unusual carbo-carbon bond cleavage by KMnO4-CuSO4 Reagent

  摘要：

  Sugars of furanose skeleton having a carbonyl or secondary hydroxyl at C-5 undergo smooth cleavage of C-4-C-5 bond with the reagent.

  DOI：

  10.1016/s0040-4039(00)91979-8

文献信息

• Highly Substituted Cyclopentane–CMP Conjugates as Potent Sialyltransferase Inhibitors
  作者：Wenming Li、Youhong Niu、De-Cai Xiong、Xiaoping Cao、Xin-Shan Ye

  DOI：10.1021/acs.jmedchem.5b01181

  日期：2015.10.22

  Sialylconjugates on cell surfaces are involved in many biological events such as cellular recognition, signal transduction, and immune response. It has been reported that aberrant sialylation at the nonreducing end of glycoconjugates and overexpression of sialyltransferases (STs) in cells are correlated with the malignance, invasion, and metastasis of tumors. Therefore, inhibitors of STs would provide valuable leads for the discovery of antitumor drugs. On the basis of the transition state of the enzyme-catalyzed sialylation reaction, we proposed that the cydopentane skeleton in its two puckered conformations might mimic the planar structure of the donor (CMP-Neu5Ac) in the transition state. A series of cydopentane-containing compounds were designed and synthesized by coupling different cydopentane alpha-hydroxyphosphonates with cytidine phosphoramidite. Their inhibitory activities against recombinant human ST6Gal-I were assayed, and a potent inhibitor 481 with a K-i of 0.028 +/- 0.006 mu M was identified. The results show that the cydopentanoid-type compounds could become a new type of sialyltransferase inhibitors as biological probes or drug leads.
• Synthesis of the Transfer-RNA Nucleoside Queuosine by Using a Chiral Allyl Azide Intermediate
  作者：Florian Klepper、Eva-Maria Jahn、Volker Hickmann、Thomas Carell

  DOI：10.1002/anie.200604579

  日期：2007.3.19
• Hill, Jason M.; Hutchinson, Edward J.; Grand, Darren M. Le, Journal of the Chemical Society. Perkin transactions I, 1994, # 11, p. 1483 - 1488
  作者：Hill, Jason M.、Hutchinson, Edward J.、Grand, Darren M. Le、Roberts, Stanley M.、Thorpe, Andrew J.、Turner, Nicholas J.

  DOI：——

  日期：——
• Papaioannou, Dionissios; Francis, George W.; Aksnes, Dagfinn W., Acta Chemica Scandinavica, 1990, vol. 44, # 1, p. 90 - 95
  作者：Papaioannou, Dionissios、Francis, George W.、Aksnes, Dagfinn W.、Brekke, Trond、Maartmann-Moe, Knut

  DOI：——

  日期：——
• Revised pathway for the biosynthesis of aristeromycin and neplanocin A from D-glucose in Streptomyces citricolor
  作者：Jason M. Hill、Gareth N. Jenkins、Cliff P. Rush、Nicholas J. Turner、Andrew J. Willetts、Antony D. Buss、Michael J. Dawson、Brian A. M. Rudd

  DOI：10.1021/ja00124a035

  日期：1995.5