1,5-anhydro-4-O-hydroxy-2,3,6-trideoxy-L-erythro-hex-1-enitol | 129985-30-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,5-anhydro-4-O-hydroxy-2,3,6-trideoxy-L-erythro-hex-1-enitol
• 英文别名: 3-deoxy-L-rhamnal；(2S,3R)-2-methyl-3,4-dihydro-2H-pyran-3-ol
• CAS: 129985-30-4
• 化学式: C₆H₁₀O₂
• 分子量: 114.144
• InChiKey: QYRNCCYXTHCRLZ-NTSWFWBYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.67
• 重原子数：
  8.0
• 可旋转键数：
  0.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  29.46
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-4-O-hydroxy-2,3,6-trideoxy-L-erythro-hex-1-enitol 在 camphor-10-sulfonic acid 、 叔丁基锂 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 (5S,7S,8R)-8-(tert-Butyl-dimethyl-silanyloxy)-7-methyl-6-oxa-spiro[4.5]decan-1-one
  参考文献：
  名称：

  Practical Synthesis of Spirocyclic Bis-C,C-glycosides. Mechanistic Models in Explanation of Rearrangement Stereoselectivity and the Bifurcation of Reaction Pathways

  摘要：

  The susceptibility of glycal-derived carbinols to acid-catalyzed ring expansion is described. In the systems prepared from cyclopentanone, Ferrier ionization precedes the pinacol-like Wagner-Meerwein shift, thermodynamic control operates, and high stereoselectivity is seen if a C(6) substituent is present. In contrast, the adducts to cyclobutanone exhibit release of ring strain under kinetically controlled conditions and intercept the oxonium species reversibly formed via direct proton transfer. The results show that the substituents positioned on the glycal ring have a pronounced influence on whether a chair-like or twist-boat transition state geometry is adopted primarily. The composite reaction profiles reveal for the first time the fundamental importance of exothermicity and of substitution in these spiro glycosidation reactions. Since optical activity is preserved in all instances, the utility of this chemistry for the synthesis of bis-C,C-glycosides and more complex oxacyclics appears promising.

  DOI：

  10.1021/jo962020i
• 作为产物：
  描述：

  4-O-(tert-butyldimethylsilyl)-L-rhodinal 在 甲醇 、 偶氮二甲酸二异丙酯 、 四丁基氟化铵 、 potassium carbonate 、 三苯基膦 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 1,5-anhydro-4-O-hydroxy-2,3,6-trideoxy-L-erythro-hex-1-enitol
  参考文献：
  名称：

  立体发散方法，涉及L-vancosamine，L-糖胺，L-柔多胺和L-香豆胺的受保护的糖合成，包括一个闭环易位步骤。

  摘要：

  在本文中，从一种常见的起始原料（-）-甲基-L-乳酸酯中报道了一种新的途径，即获得几种手性3-氨基糖作为糖基化天然产物的潜在前体。立体发散策略基于乙烯基醚的闭环复分解的实施，这是开发的反应序列的关键步骤。

  DOI：

  10.3762/bjoc.14.274

文献信息

• Application of substituent-controlled oxidative coupling of glycals in a synthesis and structural corroboration of ciclamycin 0: new possibilities for the construction of hybrid anthracyclines
  作者：Koji Suzuki、Gary A. Sulikowski、Richard W. Friesen、Samuel J. Danishefsky

  DOI：10.1021/ja00180a037

  日期：1990.11
• SUZUKI, KOJI;SULIKOWSKI, GARY A.;FRIESEN, RICHARD W.;DANISHEFSKY, SAMUEL +, J. AMER. CHEM. SOC., 112,(1990) N4, C. 8895-8902
  作者：SUZUKI, KOJI、SULIKOWSKI, GARY A.、FRIESEN, RICHARD W.、DANISHEFSKY, SAMUEL +

  DOI：——

  日期：——