4-O-acetyl-1,5-anhydro-2,6-dideoxy-L-erythro-hex-1-en-3-ulose | 68673-59-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: 4-O-acetyl-1,5-anhydro-2,6-dideoxy-L-erythro-hex-1-en-3-ulose
• 英文别名: [(2S,3S)-2-methyl-4-oxo-2,3-dihydropyran-3-yl] acetate
• CAS: 68673-59-6
• 化学式: C₈H₁₀O₄
• 分子量: 170.165
• InChiKey: RKADDPYLNFMNRF-XNCJUZBTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-O-acetyl-1,5-anhydro-2,6-dideoxy-L-erythro-hex-1-en-3-ulose 在 palladium on activated charcoal 吡啶 、 氢气 、 palladium diacetate 、 溶剂黄146 作用下， 以 乙酸乙酯 为溶剂， 反应 28.0h， 生成 (3,4-di-O-acetyl-2-deoxy-β-L-ribo-hexopyranosyl)benzene
  参考文献：
  名称：

  Palladium-mediated arylation of acetylated enones derived from glycals. 4. Synthesis of aryl-2-deoxy-.beta.-D-C-glycopyranosides

  摘要：

  The palladium-mediated arylation of the peracetylated glycal-derived enones 1, 2, and 3 afforded mixtures of C-glycosides containing an arylated enone (1a, 2a, or 3a) and an arylated ketone (1b, 2b, or 3b). A rationale for the formation of these compounds is given. Reduction of the arylated enones proceeds in a stereospecific manner, thus affording aryl 2-deoxy-beta-D-C-glycopyranosides in high yield.

  DOI：

  10.1021/jo00043a016
• 作为产物：
  描述：

  (2S,3S,6R)-4-(benzyloxy)-6-methoxy-2-methyl-3,6-dihydro-2H-pyran-3-yl acetate 在 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.08h， 以73%的产率得到4-O-acetyl-1,5-anhydro-2,6-dideoxy-L-erythro-hex-1-en-3-ulose
  参考文献：
  名称：

  己烯酮糖的合成和具有 3-氧代-糖单元的二糖库

  摘要：

  揭示了一种快速合成具有 3-氧代-糖单元的单糖和二糖的方法。几种单糖和二糖衍生的糖在三个步骤中转化为相应的己烯酮糖，包括卤代烷氧基化、脱卤化氢和酮基化反应。合成了许多 3-氧代-糖以显示该方法的重要性和普遍性。此外, 该协议成功地应用于合成一种稀有糖二糖供体单元, 作为报告的天然产物 versipelostatin 中三糖部分的一部分。

  DOI：

  10.1021/acs.joc.2c00663

文献信息

• An improved method for the preparation of 2′,3′-unsaturated nucleosides: Synthesis of stereospecifically labelled ketonucleosides
  作者：Jean Herscovici、Roland Montserret、Kostas Antonakis

  DOI：10.1016/0008-6215(88)80133-2

  日期：1988.5

  excellent yields under mild conditions by the condensation of acetylated glycals with purine or pyrimidine derivatives in the presence of trityl perchlorate. The synthesis of (α- and β-hex-2-enopyranosyl-4-ulose)theophylline nucleosides labelled at position 3′ with deuterium is described.

  摘要在高氯酸三苯酯存在下，乙酰化的糖基与嘌呤或嘧啶衍生物缩合，在温和条件下以极高的收率制备了2'，3'-不饱和核苷。描述了在3'位用氘标记的（α-和β-hex-2-enopyranosyl-4-ulose）茶碱核苷的合成。
• Synthesis of N-benzoyl-L-ristosamine and intermediates used in its
  申请人：Purdue University

  公开号：US04298726A1

  公开（公告）日：1981-11-03

  A process for synthesizing N-benzoyl-L-ristosamine is disclosed. Intermediates useful for synthesizing N-benzoyl-L-ristosamine, and processes for preparing such intermediates, are also disclosed.

  本发明揭示了一种合成N-苯甲酰-L-里斯托胺的方法。还揭示了用于合成N-苯甲酰-L-里斯托胺的中间体以及制备这些中间体的方法。
• Stereoselective Syntheses of 2-Deoxy-β-<i>C</i>-arabino- and ribopyranosides: 2-Deoxy-β-arabino- and ribopyranosyl Cyanides
  作者：Kuniaki Tatsuta、Jun Hayakawa、Yukio Tatsuzawa

  DOI：10.1246/bcsj.62.490

  日期：1989.2

  2-Deoxy-β-arabino- and ribopyranosyl cyanides, which should be suitable for the syntheses of biologically active products, were stereoselectively prepared from the reaction of the enones, 1,5-anhydro-2-deoxy-erythro-hex-1-en-3-ulose derivatives, with acetone cyanohydrin, followed by the stereoselective reduction of the producing ketones with NaBH4–CeCl3·7H2O and l-Selectride, respectively.

  由 1,5-anhydro-2-deoxy-erythro-hex-1-en-3-ulose 衍生物烯酮与丙酮氰醇反应，然后分别用 NaBH4-CeCl3-7H2O 和 l-Selectride 立体选择性还原生成的酮，立体选择性地制备了 2-脱氧-β-阿拉伯呋喃糖基和核糖呋喃糖基氰化物，这两种氰化物应适用于合成具有生物活性的产品。
• Oxidation of Fully Protected Glycals by Hypervalent Iodine Reagents
  作者：Andreas Kirschning

  DOI：10.1021/jo00110a028

  日期：1995.3

  A new application of organoiodine(III) is presented. Fully protected glycals are directly converted into 2,3-dihydro-4H-pyran-4-ones by [hydroxy(tosyloxy)iodo]benzene (PhI(OH)OTs, 1). The detailed study reveals that this conversion is independent of the relative stereochemistry as well as the nature of protection on the pyran ring. 3-O-Silyl groups are most smoothly converted into the keto group giving 2,3-dihydro-4H-pyran-4-ones in yields up to 74%. In contrast, 4,6-di-O-acetyl-3-deoxyglucal (19) affords the rearranged oxidation product 32. Both observations can be reconciled by the proposed mechanism.
• The total synthesis of avermectin A1a
  作者：Samuel J. Danishefsky、David M. Armistead、Francine E. Wincott、Harold G. Selnick、Randall Hungate

  DOI：10.1021/ja00190a034

  日期：1989.4