(+)-(2R,3R) Methyl 3,4-O-isopropylidene-2-methoxybutanoate | 151867-36-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (+)-(2R,3R) Methyl 3,4-O-isopropylidene-2-methoxybutanoate
• 英文别名: methyl (2R,3R)-3,4-(isopropylidenedioxy)-2-methoxybutanoate；methyl (2R)-2-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-methoxyacetate
• CAS: 151867-36-6
• 化学式: C₉H₁₆O₅
• 分子量: 204.223
• InChiKey: HDEFGPXPAXNZAH-RNFRBKRXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 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：

  (+)-(2R,3R) Methyl 3,4-O-isopropylidene-2-methoxybutanoate 在 三氟甲磺酸 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 环己烷 、 水 为溶剂， 反应 3.0h， 生成 (-)-(2R,3R)-3-Benzyloxy-4-hydroxy-2-methoxybutanoic acid 1,4-lactone
  参考文献：
  名称：

  Stereoselective total synthesis of bengamide E from glyceraldehyde acetonide and a nonracemic .gamma.-alkoxy allylic stannane

  摘要：

  The synthesis of bengamide E (30) was achieved starting from the furan adduct 1 of (R)-glyceraldehyde acetonide. The key step entailed MgBr2-promoted addition of the (S)-gamma-alkoxy allylic stannane (S)-25 to the aldehyde 8 obtained from the oxidation product of furan 1 after protection as the methyl ether. The adduct of stannane (S)-25 and aldehyde 8, a 1:1 mixture of hydroxy ester 27 and lactone 28 was converted to bengamide E by aminolysis with (S)-2-aminocaprolactam and subsequent debenzylation with Li in NH3.

  DOI：

  10.1021/jo00075a017
• 作为产物：
  描述：

  2,2-dimethyl-4-(2-furyl)hydroxymethyl-1,3-dioxolane 在 ruthenium(IV) oxide 、 sodium periodate 、 sodium hydride 、 碳酸氢钠 作用下， 以 四氢呋喃 、 四氯化碳 、 乙醚 、 水 、 乙腈 为溶剂， 反应 0.42h， 生成 (+)-(2R,3R) Methyl 3,4-O-isopropylidene-2-methoxybutanoate
  参考文献：
  名称：

  Stereoselective total synthesis of bengamide E from glyceraldehyde acetonide and a nonracemic .gamma.-alkoxy allylic stannane

  摘要：

  The synthesis of bengamide E (30) was achieved starting from the furan adduct 1 of (R)-glyceraldehyde acetonide. The key step entailed MgBr2-promoted addition of the (S)-gamma-alkoxy allylic stannane (S)-25 to the aldehyde 8 obtained from the oxidation product of furan 1 after protection as the methyl ether. The adduct of stannane (S)-25 and aldehyde 8, a 1:1 mixture of hydroxy ester 27 and lactone 28 was converted to bengamide E by aminolysis with (S)-2-aminocaprolactam and subsequent debenzylation with Li in NH3.

  DOI：

  10.1021/jo00075a017

文献信息

• Organocatalytic and Scalable Synthesis of the Anti-Influenza Drugs Zanamivir, Laninamivir, and CS-8958
  作者：Junshan Tian、Jiankang Zhong、Yunsheng Li、Dawei Ma

  DOI：10.1002/anie.201408138

  日期：2014.12.8

  Zanamivir, laninamivir, and CS‐8958 are three neuraminidase inhibitors that have been clinically used to combat influenza. We report herein a novel organocatalytic route for preparing these agents. Only 13 steps are needed for the assembly of zanamivir and laninamivir from inexpensive D‐araboascorbic acid by this synthetic route, which relies heavily on a thiourea‐catalyzed enantioselective Michael

  扎那米韦，拉尼米韦和CS-8958是三种神经氨酸酶抑制剂，已在临床上用于抗击流感。我们在本文中报道了用于制备这些试剂的新颖的有机催化途径。通过这种合成路线，从廉价的D-阿拉伯抗坏血酸组装扎那米韦和拉尼米韦仅需13个步骤，该步骤主要依赖于硫脲催化的对映选择性迈克尔将丙酮加到叔丁基（2-硝基乙烯基）氨基甲酸酯和一种抗-氨基苯甲酸中。生成的迈克尔加合物与由D-阿拉伯抗坏血酸制得的醛的选择性亨利反应。从制备超过3.5克的扎那米韦中可以明显看出，合成方法是可扩展的。
• Peramivir analogues bearing hydrophilic side chains exhibit higher activities against H275Y mutant than wild-type influenza virus
  作者：Din-Chi Chiu、Tzu-Chen Lin、Wen-I Huang、Ting-Jen Cheng、Keng-Chang Tsai、Jim-Min Fang

  DOI：10.1039/c7ob02374j

  日期：——

  reduced. The previously reported cocrystal structures of inhibitors in the mutant neuraminidase (NA) suggest that the hydrophobic side chain should be at the origin of reduced binding affinity. In contrast, zanamivir having a hydrophilic glycerol side chain still possesses high affinity toward the H275Y NA. We thus designed five peramivir analogues (5–9) carrying hydrophilic glycol or glycerol side chains

  帕拉米韦在流感的临床治疗中是一种有效的抗流感药物，但其对H275Y突变体的功效降低。先前报道的突变神经氨酸酶（NA）中抑制剂的共晶体结构表明，疏水性侧链应位于结合亲和力降低的起点。相反，具有亲水性甘油侧链的扎那米韦仍然对H275Y NA具有高亲和力。因此，我们设计了五个peramivir类似物（5–9）带有亲水性乙二醇或甘油侧链，并评估了它们在抗流感活性中的作用，尤其是对于H275Y突变体。合成序列涉及烯烃和腈氧化物之间的（3 + 2）环加成反应的关键步骤，以构建携带所需亲水性侧链和其他适当官能团的帕拉米韦支架。分子对接实验表明，亲水性侧链可以与H275Y NA活性位点中转移的Glu-276残基提供额外的氢键。因此，对于携带亲水性侧链的peramivir类似物，H275Y突变体可能比野生型病毒更敏感。值得注意的是，带有甘油侧链的peramivir类似物具有IC 50抑制H275Y突变体 值是35
• Convergent synthesis of tetrahydropyranyl side chain of verucopeptin, an antitumor antibiotic active against multidrug-resistant cancers
  作者：Yuanjun Sun、Wenhao Tang、Huxin Ni、Mei Wang、Bin Huang、Ya-Qiu Long

  DOI：10.1039/d2cc04529j

  日期：——

  A concise synthesis of the tetrahydropyranyl side chain of verucopeptin, an antitumor antibiotic cyclodepsipeptide efficacious against MDR cancers in vivo, is achieved using 12 steps in the longest linear sequence and 21 total steps, in which Julia–Kocienski olefination for the segments coupling, asymmetric hydroxylation as well as stereoselective synthesis of stable tetrahydropyran ring from a D-isoascorbic

  verucopeptin 的四氢吡喃基侧链的简明合成，一种抗肿瘤抗生素 cyclodepsipeptide，对体内MDR 癌症有效，使用最长线性序列中的 12 个步骤和总共 21 个步骤实现，其中 Julia-Kocienski 烯化用于链段偶联，不对称羟基化以及从D-异抗坏血酸衍生物立体选择性合成稳定的四氢吡喃环是关键步骤。这种收敛的合成策略使 verucopeptin 的结构修饰和机制研究能够用于其临床应用。
• Stereoselective total synthesis of bengamide E from glyceraldehyde acetonide and a nonracemic .gamma.-alkoxy allylic stannane
  作者：James A. Marshall、George P. Luke

  DOI：10.1021/jo00075a017

  日期：1993.11

  The synthesis of bengamide E (30) was achieved starting from the furan adduct 1 of (R)-glyceraldehyde acetonide. The key step entailed MgBr2-promoted addition of the (S)-gamma-alkoxy allylic stannane (S)-25 to the aldehyde 8 obtained from the oxidation product of furan 1 after protection as the methyl ether. The adduct of stannane (S)-25 and aldehyde 8, a 1:1 mixture of hydroxy ester 27 and lactone 28 was converted to bengamide E by aminolysis with (S)-2-aminocaprolactam and subsequent debenzylation with Li in NH3.