ethyl 2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranoside | 294669-49-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: ethyl 2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranoside
• 英文别名: [(2R)-2-benzoyloxy-2-[(2S,3S,4R,5S)-3,4-dibenzoyloxy-5-ethylsulfanyloxolan-2-yl]ethyl] benzoate
• CAS: 294669-49-1
• 化学式: C₃₆H₃₂O₉S
• 分子量: 640.711
• InChiKey: NWAMYACHPFIITG-BOMVZYKJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  46
• 可旋转键数：
  16
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  ethyl 2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranoside 在 N-碘代丁二酰亚胺 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 生成 8-methoxycarbonyloctyl β-D-galactofuranoside
  参考文献：
  名称：

  A NEW APPROACH TO A DISACCHARIDIC HAPTEN CONTAINING A GALACTOFURANOSYL ENTITY

  摘要：

  A short synthetic entry into the disaccharidic hapten beta-D-Galf-(1-->3)-alpha-D-Manp-O(CH2)(8)CO2Me containing a galactofuranosyl entity at the non-reducing part is described. The synthetic scheme was designed in such a way that each required building block could be obtained by minimizing the number of chemical and purification steps. Indeed, compound 8 was obtained according to a four step-one pot preparation.

  DOI：

  10.1081/car-100108662
• 作为产物：
  描述：

  [(2R)-2-benzoyloxy-2-[(2S,3S,4R)-3,4-dibenzoyloxy-5-octoxyoxolan-2-yl]ethyl] benzoate 在 硫酸 、 三氟化硼乙醚 、 三氟乙酸酐 作用下， 以 二氯甲烷 为溶剂， 生成 ethyl 2,3,5,6-tetra-O-benzoyl-1-thio-β-D-galactofuranoside
  参考文献：
  名称：

  亚磺酰基半乳糖呋喃糖苷的硫原子构型决定了糖基化反应中不同的反应性

  摘要：

  亚磺酰基β-d-半乳糖呋喃糖苷3（R，S）和9（R，S）被用作糖基化反应中的新的呋喃呋喃糖基供体。三氟甲磺酸酐的活化涉及不同的反应途径，这取决于硫原子的立体化学。实验结果强调了3（R）和9（R）分别比3（S）和9（S）更适合用于合成β-d-半乳糖呋喃糖苷。

  DOI：

  10.1016/s0040-4039(00)00887-x

文献信息

• Total Synthesis of Marine Glycosphingolipid Vesparioside B
  作者：Peng-Cheng Gao、San-Yong Zhu、Hui Cao、Jin-Song Yang

  DOI：10.1021/jacs.5b12589

  日期：2016.2.10

  The first total synthesis of a major component of marine glycolipid vesparioside B ( Scheme 1 , 1, R1 = n-C22H45, R2 = n-C14H29) has been accomplished through a convergent [4 + 3] coupling strategy. Key steps included stereoselective installment of a set of challenging 1,2-cis-glycoside bonds. A 2-quinolinecarbonyl-assisted α-galactosylation and a novel β-arabinosylation were developed, respectively

  海洋糖脂 vesparioside B 的主要成分的首次全合成（方案 1, 1, R1 = n-C22H45, R2 = n-C14H29）已通过收敛 [4 + 3] 耦合策略完成。关键步骤包括立体选择性安装一组具有挑战性的 1,2-顺式糖苷键。分别开发了 2-喹啉羰基辅助的 α-半乳糖基化和新型 β-阿拉伯糖基化，以合成 α-呋喃半乳糖苷和 β-阿拉伯吡喃糖苷键。此外，4,6-O-亚苄基控制的α-吡喃半乳糖基化反应允许左侧四糖供体2与右侧二糖脂质受体3有效连接，从而导致1的全合成。
• Chloramine-T-mediated chemoselective hydrolysis of thioglycosides into glycosyl hemiacetals under neutral conditions
  作者：Anup Kumar Misra、Geetanjali Agnihotri

  DOI：10.1016/j.carres.2003.12.020

  日期：2004.3

  A metal-free, mild, efficient and chemoselective hydrolysis of several thioalkylglycosides (1) into their corresponding 1-hydroxy sugars (2) using sodium N-chloro-p-toluenesulfonamide trihydrate (chloramine-T) without affecting other functional groups is reported. (C) 2004 Published by Elsevier Ltd.
• A NEW APPROACH TO A DISACCHARIDIC HAPTEN CONTAINING A GALACTOFURANOSYL ENTITY
  作者：Vincent Ferrières、Myriam Roussel、Muriel Gelin、Daniel Plusquellec

  DOI：10.1081/car-100108662

  日期：2001.12.31

  A short synthetic entry into the disaccharidic hapten beta-D-Galf-(1-->3)-alpha-D-Manp-O(CH2)(8)CO2Me containing a galactofuranosyl entity at the non-reducing part is described. The synthetic scheme was designed in such a way that each required building block could be obtained by minimizing the number of chemical and purification steps. Indeed, compound 8 was obtained according to a four step-one pot preparation.
• Sulfur atom configuration of sulfinyl galactofuranosides determines different reactivities in glycosylation reactions
  作者：Vincent Ferrières、Jérôme Joutel、Rachel Boulch、Myriam Roussel、Loı̈c Toupet、Daniel Plusquellec

  DOI：10.1016/s0040-4039(00)00887-x

  日期：2000.7

  Sulfinyl β-d-galactofuranosides 3(R,S) and 9(R,S) were used as new hexofuranosyl donors in glycosylation reactions. Activation by trifluoromethanesulfonic anhydride involved different reaction pathways depending on the stereochemistry at the sulfur atom. Experimental results underlined a more suitable reactivity of 3(R) and 9(R) versus 3(S) and 9(S), respectively, for the synthesis of β-d-galactofuranosides

  亚磺酰基β-d-半乳糖呋喃糖苷3（R，S）和9（R，S）被用作糖基化反应中的新的呋喃呋喃糖基供体。三氟甲磺酸酐的活化涉及不同的反应途径，这取决于硫原子的立体化学。实验结果强调了3（R）和9（R）分别比3（S）和9（S）更适合用于合成β-d-半乳糖呋喃糖苷。