4,6-di-O-benzyl-1,5-anhydro-D-erythrohex-2-enitol | 850753-00-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 4,6-di-O-benzyl-1,5-anhydro-D-erythrohex-2-enitol
• 英文别名: (2R,3S) 3-Benzyloxy-2-benzyloxymethyl-3,6-dihydro-2H-pyran；(2R,3S)-3-phenylmethoxy-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran
• CAS: 850753-00-3
• 化学式: C₂₀H₂₂O₃
• 分子量: 310.393
• InChiKey: KKMXQLNJHWXPDU-VQTJNVASSA-N

物化性质

• 沸点：
  443.4±45.0 °C(Predicted)
• 密度：
  1.12±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  4,6-di-O-benzyl-1,5-anhydro-D-erythrohex-2-enitol 在 RhCl(PPh₃)3 四氧化锇 、 N-甲基吲哚酮 、 samarium diiodide 、 camphor-10-sulfonic acid 、 四氯化锡 、 potassium carbonate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 生成 Acetic acid (4aS,5aR,6aS,7aR,9S,10R,11aS,12R,12aS,13aR,14R,14aS)-14-acetoxy-9-benzyloxy-10-benzyloxymethyl-7a-methoxy-hexadecahydro-1,5,7,11,13-pentaoxa-pentacen-12-yl ester
  参考文献：
  名称：

  反式多环醚骨架α-螺旋模拟支架的设计与合成

  摘要：

  受强力海洋毒素的共同骨骼特征的启发，设计了梯状多环醚支架，作为合成结构明确的α-螺旋模拟物的基础。提出了合成反式6/6/6/6/6五环醚骨架的合成方法，该方法涉及经由SmI 2介导的α-磺酰基酮与醛的偶联反应，四氢吡喃环的迭代组装。

  DOI：

  10.1016/j.tetlet.2005.02.039
• 作为产物：
  描述：

  3,4,6-三苄氧基-D-葡萄烯糖 在 碘 PMHS 作用下， 以 二氯甲烷 为溶剂， 反应 4.0h， 以90%的产率得到4,6-di-O-benzyl-1,5-anhydro-D-erythrohex-2-enitol
  参考文献：
  名称：

  First example of the activation of polymethylhydrosiloxane with molecular iodine: a facile synthesis of 3,6-dihydropyran derivatives

  摘要：

  Glyeals react rapidly with polymethylhydrosiloxane (PMHS) in the presence of a catalytic amount of molecular iodine under mild conditions to afford the corresponding 3,6-dihydropyran derivatives in excellent yields. Et3SiH/I-2 was also found to be effective for this conversion. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2005.02.068

文献信息

• Base-Mediated Transformation of Glycals to Their Corresponding Vinyl Iodides and Their Application in the Synthesis of C-3 Enofuranose and Bicyclic 3,4-Pyran-Fused Furanose
  作者：Norein Sakander、Ajaz Ahmed、Irshad Ahmad Zargar、Debaraj Mukherjee

  DOI：10.1021/acs.joc.3c00302

  日期：2023.7.7

  A simple method for the iodination of unsaturated sugars to form sugar vinyl iodides was developed under oxidant-free conditions using NaH/DMF/iodine as a reagent system at ambient temperature. 2-Iodoglycals bearing ester, ether, silicon, and acetonide protection were synthesized in good to excellent yield. 3-Vinyl iodides derived from 1,2:5,6-diacetonide glucofuranose were transformed to C-3 enofuranose

  开发了一种在无氧化剂条件下使用 NaH/DMF/碘作为试剂系统在环境温度下将不饱和糖碘化形成糖乙烯基碘的简单方法。合成了带有酯、醚、硅和丙酮化物保护的2-碘糖，收率良好至优异。衍生自 1,2:5,6-二丙酮呋喃葡萄糖的 3-乙烯基碘化物通过 Pd 催化的 C-3 羰基化和分子内 Heck 反应分别转化为 C-3 依诺呋喃糖和双环 3,4-吡喃稠合呋喃糖，如下所示：关键一步。
• 1′,5′-Anhydro-<scp>l</scp>-<i>ribo</i>-hexitol Adenine Nucleic Acids (α-<scp>l</scp>-HNA-A): Synthesis and Chiral Selection Properties in the Mirror Image World
  作者：Daniele D’Alonzo、Mathy Froeyen、Guy Schepers、Giovanni Di Fabio、Arthur Van Aerschot、Piet Herdewijn、Giovanni Palumbo、Annalisa Guaragna

  DOI：10.1021/acs.joc.5b00406

  日期：2015.5.15

  The synthesis and a preliminary investigation of the base pairing properties of (6' -> 4']-linked 1',5'-anhydro-L-ribohexitol nucleic acids (alpha-L-HNA) have herein been reported through the study of a model oligoadenylate system in the mirror image world. Despite its considerable preorganization due to the rigidity of the "all equatorial" pyranyl sugar backbone, a-L-HNA represents a versatile informational biopolymer, in view of its capability to cross-communicate with natural and unnatural complements in both enantiomeric forms. This seems the result of an inherent flexibility of the oligonucleotide system, as witnessed by the singular formation of iso- and heterochiral associations composed of regular, enantiomorphic helical structures. The peculiar properties of alpha-L-HNA (and most generally of the alpha-HNA system) provide new elements in our understanding of the structural prerequisites ruling the stereoselectivity of the hybridization processes of nucleic acids.
• Design and synthesis of a trans-fused polycyclic ether skeleton as an α-helix mimetic scaffold
  作者：Hiroki Oguri、Akifumi Oomura、Shintaro Tanabe、Masahiro Hirama

  DOI：10.1016/j.tetlet.2005.02.039

  日期：2005.3

  Inspired by the common skeletal feature of potent marine toxins, a ladder-like polycyclic ether scaffold was designed as the basis for the synthesis of structurally defined α-helix mimics. A synthetic route to trans-fused 6/6/6/6/6 pentacyclic ether skeletons is presented, involving the iterative assembly of tetrahydropyran rings via the SmI2-mediated coupling reaction of α-sulfonyl ketones with aldehydes

  受强力海洋毒素的共同骨骼特征的启发，设计了梯状多环醚支架，作为合成结构明确的α-螺旋模拟物的基础。提出了合成反式6/6/6/6/6五环醚骨架的合成方法，该方法涉及经由SmI 2介导的α-磺酰基酮与醛的偶联反应，四氢吡喃环的迭代组装。
• First example of the activation of polymethylhydrosiloxane with molecular iodine: a facile synthesis of 3,6-dihydropyran derivatives
  作者：J.S. Yadav、B.V. Subba Reddy、K. Premalatha、T. Swamy

  DOI：10.1016/j.tetlet.2005.02.068

  日期：2005.4

  Glyeals react rapidly with polymethylhydrosiloxane (PMHS) in the presence of a catalytic amount of molecular iodine under mild conditions to afford the corresponding 3,6-dihydropyran derivatives in excellent yields. Et3SiH/I-2 was also found to be effective for this conversion. (c) 2005 Elsevier Ltd. All rights reserved.