1,2-O-isopropylidene-D-erythrose | 14048-37-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-D-erythrose
• 英文别名: 1,2-O-Isopropyliden-D-erythrose；(3aR,6R,6aR)-2,2-dimethyltetrahydrofuro[2,3-d][1,3]dioxol-6-ol；(3aR,6R,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-ol
• CAS: 14048-37-4
• 化学式: C₇H₁₂O₄
• 分子量: 160.17
• InChiKey: GCDHRQSHVCHCIJ-HSUXUTPPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-D-erythrose 在 oxonium 作用下， 生成 (2R,3R)-2,3,4-三羟基丁醛
  参考文献：
  名称：

  差异保护的酒石醛的新型合成等同物。一个简单的途径来获得有用的c-4手性合成子。

  摘要：

  据报道由D-葡萄糖合成4-乙酰氧基-3-O-苄基-1,2-O-异亚丙基醛糖苷酶。这些酒石醛的合成当量在乙酰氧基化中心被化学选择性还原，从而产生了一系列有用的差异保护的C-4手性合成子。

  DOI：

  10.1016/s0040-4039(00)82295-9
• 作为产物：
  描述：

  1,2-O-异丙基-α-D-呋喃核糖 在 偶氮二异丁腈 、 偶氮二甲酸二叔丁酯 、 三正丁基氢锡 、 三苯基膦 作用下， 以 四氢呋喃 、 苯 为溶剂， 反应 12.0h， 生成 1,2-O-isopropylidene-D-erythrose
  参考文献：
  名称：

  内部氢键相互作用对伯烷氧基自由基β-断裂的有益作用。d-木糖基和d-呋喃糖酶的两步转化分别为l-苏糖和d-赤藓糖

  摘要：

  伯烷氧基自由基是在还原条件下由其易于合成的N-邻苯二甲酰亚胺基衍生物生成的。衍生自其相应的木糖和呋喃呋喃糖衍生物的伯烷氧基自由基仅经历异常的β片段化，分别得到1-苏糖和d-赤藓糖衍生物。发生这种情况是因为烷氧基能够实现内部氢键相互作用，从而导致稳定的六元环分子内氢键结构。当羟基被保护时，阻止了β-片段化途径，并且发生了氢原子转移（HAT）途径。计算研究为实验观察提供了有力的支持。

  DOI：

  10.1021/jo0709551

文献信息

• Apralogs: Apramycin 5-<i>O</i>-Glycosides and Ethers with Improved Antibacterial Activity and Ribosomal Selectivity and Reduced Susceptibility to the Aminoacyltransferase (3)-IV Resistance Determinant
  作者：Jonathan C. K. Quirke、Parasuraman Rajasekaran、Vikram A. Sarpe、Amr Sonousi、Ivan Osinnii、Marina Gysin、Klara Haldimann、Qiao-Jun Fang、Dimitri Shcherbakov、Sven N. Hobbie、Su-Hua Sha、Jochen Schacht、Andrea Vasella、Erik C. Böttger、David Crich

  DOI：10.1021/jacs.9b11601

  日期：2020.1.8

  Apramycin is a structurally unique member of the 2-deoxystreptamine class of aminoglycoside antibiotics characterized by a mono-substituted 2-deoxystreptamine ring that carries an unusual bicyclic eight-carbon dialdose moiety. Because of its unusual structure apramycin is not susceptible to the most prevalent mechanisms of aminoglycoside resistance including the aminoglycoside-modifying enzymes and

  安普霉素是 2-脱氧链霉胺类氨基糖苷类抗生素的一种结构独特的成员，其特征在于带有一个不寻常的双环八碳二糖部分的单取代 2-脱氧链霉胺环。由于其不寻常的结构，安普霉素不易受到最普遍的氨基糖苷类耐药机制的影响，包括氨基糖苷类修饰酶和核糖体甲基转移酶，它们的广泛存在严重损害了当前临床实践中的所有氨基糖苷类。这些特性与动物模型中最低的耳毒性相结合，使安普霉素成为开发下一代氨基糖苷类抗生素治疗多重耐药细菌感染（尤其是 ESKAPE 病原体）的极好起点。考虑到这一点，我们描述了设计，合成和评估三个系列的安普霉素衍生物，均在 5 位官能化，目的是在不牺牲细菌和真核核糖体之间选择性的情况下提高抗菌效力，并克服罕见的氨基糖苷乙酰转移酶 (3)-IV 类氨基糖苷类修饰酶，它构成了对安普霉素的抗菌素耐药性的唯一记录机制。我们表明几种 apramycin-5-O-β-D-呋喃核糖苷、5-O-β-D-eryrthofuranosides
• Synthesis of 3′-S-Phosphonomethyl-Modified Nucleoside Phosphonates with a 3′-Deoxy-3′-thio-α-L-threosyl Sugar Moiety
  作者：Qiuya Huang、Piet Herdewijn

  DOI：10.1002/ejoc.201100177

  日期：2011.7

  The synthesis and antiviral evaluation of 3′-deoxy-3′-S-phosphonomethyl-3′-thio-α-L-threosyl nucleosides as well as the 2′-deoxy analogues related to PMDTT are described. The key transformations involved the synthesis of the 3′-deoxy-3′-thio-L-threosyl and the 2′,3′-dideoxy-3′-thio-L-threosyl derivatives by the Mitsunobu reaction. The phosphonate function was introduced by nucleophilic substitution

  描述了 3'-deoxy-3'-S-phosphonomethyl-3'-thio-α-L-threosyl 核苷以及与 PMDTT 相关的 2'-deoxy 类似物的合成和抗病毒评估。关键的转化涉及通过 Mitsunobu 反应合成 3'-deoxy-3'-thio-L-threosyl 和 2',3'-dideoxy-3'-thio-L-threosyl 衍生物。通过亲核取代引入膦酸酯功能，并在 Vorbruggen 条件下进行糖基化。这些合成化合物均未显示出显着的体外抗 HIV、HCV 和 RSV 活性或细胞毒性。
• Synthesis of Carbohydrates in Mineral-Guided Prebiotic Cycles
  作者：Hyo-Joong Kim、Alonso Ricardo、Heshan I. Illangkoon、Myong Jung Kim、Matthew A. Carrigan、Fabianne Frye、Steven A. Benner

  DOI：10.1021/ja201769f

  日期：2011.6.22

  One present obstacle to the "RNA-first" model for the origin of life is an inability to generate reasonable "hands off" scenarios for the formation of carbohydrates under conditions where they might have survived for reasonable times once formed. Such scenarios would be especially compelling if they deliver pent(ul)oses, five-carbon sugars found in terran genetics, and exclude other carbohydrates (e.g., aldotetroses) that may also be able to function in genetic systems. Here, we provide detailed chemical analyses of carbohydrate premetabolisin, showing how borate, molybdate, and calcium minerals guide the formation of tetroses (C(4)H(8)O(4)), heptoses (C(7)H(14),O(7)), and pentoses (C(5)H(10)O(5)), including the ribose found in RNA, in "hands off" experiments, starting with formaldehyde and glycoaldehyde. These results show that pent(ul)oses would almost certainly have formed as stable borate complexes on the surface of an early Earth beneath a humid CO(2) atmosphere suffering electrical discharge. While aldotetroses form extremely stable complexes with borate, they are not accessible by pathways plausible under the most likely early Earth scenarios. The stabilization by borate is not, however, absolute. Over longer times, material is expected to have passed from borate-bound pent(ul)oses to a branched heptulose, which is susceptible to Cannizzaro reduction to give dead end products. We show how this fate might be avoided using molybdate-catalyzed rearrangement of a branched pentose that is central to borate-moderated cycles that fix carbon from formaldehyde. Our emerging understanding of the nature of the early Earth, including the presence of hydrated rocks undergoing subduction to form felsic magmas in the early Hadean eon, may have made borate and molydate species available to prebiotic chemistry, despite the overall "reduced" state of the planet.
• Fragmentation of carbohydrate anomeric alkoxy radicals. Tandem .beta.-fragmentation-cyclization of alcohols
  作者：Pedro de Armas、Cosme G. Francisco、Ernesto Suarez

  DOI：10.1021/ja00072a060

  日期：1993.9
• DHAVALE, DILIP D.;TAGLIAVINI, EMILIO;TROMBINI, CLAUDIO;UMANI-RONCHI, ACHI+, TETRAHEDRON LETT., 29,(1988) N 47, C. 6163-6166
  作者：DHAVALE, DILIP D.、TAGLIAVINI, EMILIO、TROMBINI, CLAUDIO、UMANI-RONCHI, ACHI+

  DOI：——

  日期：——