Methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-pyranoside | 64551-84-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: Methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-pyranoside
• 英文别名: Methyl-4,6-di-O-acetyl-2,3-dideoxy-α-D-glucopyranosid；methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hexopyranoside；methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-glucopyranoside；methyl 2,3-dideoxy-4,6-di-O-acetyl-α-D-glucopyranoside；((2R,3S,6S)-3-Acetoxy-6-methoxytetrahydro-2H-pyran-2-yl)methyl acetate；[(2R,3S,6S)-3-acetyloxy-6-methoxyoxan-2-yl]methyl acetate
• CAS: 64551-84-4
• 化学式: C₁₁H₁₈O₆
• 分子量: 246.26
• InChiKey: XHUMGZABGNVWGH-AXFHLTTASA-N

物化性质

• 沸点：
  113 °C(Press: 0.1 Torr)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  17
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-pyranoside 在 草酰氯 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 1.0h， 生成 (4S,5R,6S)-4-[(S)-3-(tert-Butyl-dimethyl-silanyl)-1-methoxy-prop-2-ynyl]-6-[(E)-(1S,4R,5S,10S)-10-(tert-butyl-dimethyl-silanyloxy)-4,5-dimethoxy-1-methyl-10-phenyl-dec-2-enyl]-2,2,5-trimethyl-[1,3]dioxane
  参考文献：
  名称：

  Abel, Stephan; Faber, Dominik; Hueter, Ottmar, Angewandte Chemie, 1994, vol. 106, # 23/24, p. 2522 - 2523

  摘要：

  DOI：
• 作为产物：
  描述：

  methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 生成 Methyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-pyranoside
  参考文献：
  名称：

  Diastereoselective Synthesis of 2′,3′-Dideoxy- β-C- Glucopyranosides as Intermediates for the Synthesis of 2′,3′-Dideoxy-β-D-Glucopyranosyl-C-Nucleosides

  摘要：

  An extension of the Vorbruggen method of nucleotide synthesis for the synthesis of G glucopyranosides, as intermediates for C-nucleosides, is described. It could be shown that the diastereoselectivity of the reaction can be tuned by a simple change of protecting groups.

  DOI：

  10.1080/15257770701508695

文献信息

• NMR assisted design of high affinity ligands for structurally uncharacterized proteins
  申请人：——

  公开号：US20020042150A1

  公开（公告）日：2002-04-11

  Methods of using NMR spectroscopy for identifying ligands that bind to structurally uncharacterized proteins, and for improving the binding affinity of ligands for biological targets, which in one aspect comprises: a) preparing first NMR spectra of a first complex comprising the biological target and a paramagnetically labeled derivative of a first ligand; b) preparing second NMR spectra of a second complex comprising the biological target and a second ligand; and c) analyzing the spectra to determine whether the second ligand binds to the biological target within the paramagnetic zone of the paramagnetically labeled derivative; wherein steps (a) and (b) are performed simultaneously, consecutively, or in any order.

  利用核磁共振光谱鉴定与结构上未定性的蛋白质结合的配体以及提高配体与生物靶标结合亲和力的方法，其中一个方面包括 a) 制备包含生物靶标和第一配体的顺磁标记衍生物的第一复合物的第一核磁共振谱； b) 制备包含生物靶标和第二配体的第二复合物的第二核磁共振光谱；以及 c) 分析光谱以确定第二配体是否在顺磁标记衍生物的顺磁区内与生物靶标结合； 其中步骤(a)和(b)可同时、连续或以任何顺序执行。
• Traceless Chiral Auxiliaries for the Allene Ether Nazarov Cyclization
  作者：April R. Banaag、Marcus A. Tius

  DOI：10.1021/jo801503c

  日期：2008.11.7

  The key stereochemical factors that determine transfer of asymmetry from the chiral auxiliary to the cyclopentenone in the allene ether version of the Nazarov reaction have been elucidated. On the basis of the new insights into the mechanism, two highly effective chiral auxiliaries were designed and prepared.
• Design of Chiral Auxiliaries for the Allene Ether Nazarov Cyclization
  作者：April R. Banaag、Marcus A. Tius

  DOI：10.1021/ja069342g

  日期：2007.5.1

  A 1,3- or a 1,4-cis axial tert-butyldimethylsilyloxy substituent on the pyranose derived chiral auxiliary for the allene ether Nazarov cyclization leads to products in high optical purity. alpha-Pyranose and beta-pyranose derived auxiliaries lead to enantiomeric products.
• Simple Designs for the Construction of Complex trans-Fused Polyether Toxin Frameworks. A Linear Strategy Based on Entropically Favored Oxirane Ring Enlargement in Epoxycycloalkenes Followed by Carbon-Carbon or Carbon-Oxygen Bond-Forming Cyclizations
  作者：Eleuterio Alvarez、Maria T. Diaz、Ricardo Perez、Jose L. Ravelo、Alicia Regueiro、Jose A. Vera、Dacil Zurita、Julio D. Martin

  DOI：10.1021/jo00089a034

  日期：1994.5

  A successful design for the construction of trans-fused medium-size cyclic ethers is described. The key features of the synthesis are as follows: (i) intramolecular oxirane ring expansion in cycloalkenes to give bridged oxabicyclic systems and (ii) linear, one- or two-directional synthetic operations which generate external oxocycles in single reaction steps. The general approach involves the intramolecular addition of a stable gamma-alkoxy-substituted allylstannane to an aldehyde carbonyl group, and the entire reaction is conducted in a one-pot process which includes the following: (i) vic-diol fragmentation from the bridged oxabicyclic precursor and (ii) Lewis acid-induced cyclization of the resulting aldehyde-allylic tin system. While the present strategy was mostly developed around racemic models, the potential for adoption of;enantioselective features is immediate. The versatility, scope, limitations, and potential applications of the present technology are discussed in detail.
• Menicagli, Rita; Malanga, Corrado; Pecunioso, Angelo, Gazzetta Chimica Italiana, 1985, vol. 115, # 1, p. 23 - 28
  作者：Menicagli, Rita、Malanga, Corrado、Pecunioso, Angelo、Lardicci, Luciano

  DOI：——

  日期：——