(R,R)-3,4,6-tri-o-benzoyl-1,2-o-propynylorthobenzoyl-α-D-galactopyranose | 953795-90-9

• 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: (R,R)-3,4,6-tri-o-benzoyl-1,2-o-propynylorthobenzoyl-α-D-galactopyranose
• 英文别名: [(3aR,5R,6S,7S,7aR)-6,7-dibenzoyloxy-2-phenyl-2-prop-2-ynoxy-5,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-b]pyran-5-yl]methyl benzoate
• CAS: 953795-90-9
• 化学式: C₃₇H₃₀O₁₀
• 分子量: 634.639
• InChiKey: JWQDPFKSUXOIFO-NCDIZUBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  47
• 可旋转键数：
  13
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  116
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  (R,R)-3,4,6-tri-o-benzoyl-1,2-o-propynylorthobenzoyl-α-D-galactopyranose 在 gold(III) bromide 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 14.08h， 生成 2-(methacrylamido)ethyl 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranoside
  参考文献：
  名称：

  Gold catalyzed glycosidations for the synthesis of sugar acrylate/acrylamide hybrids and their utility

  摘要：

  Propargyl glyco 1,2-orthoesters were exploited for the efficient synthesis of interesting glycomonomers such as glyco-acrylates and acrylamides using gold catalysts. It was observed that propargyl glyco 1,2-orthoesters with hydroxyethyl acrylates gives very good yield of the corresponding glyco-acrylates in a single step in the presence of catalytic amount of gold(III) catalyst; whereas, gold catalyzed glycosidation reaction on hydroxyethyl acrylamides was found to yield the corresponding acrylamidoyl 1,2-orthoester which was then converted to the corresponding glycol-acrylamide in the presence of catalytic amount of TMSOTf. Synthesized glyco-acrylate/acrylamide monomers are shown to undergo thiolate addition as well as free radical polymerization (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2011.04.018
• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzoyl-α-D-galactopyranosyl bromide 、 2-丙炔-1-醇 在 2,6-二甲基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 48.0h， 生成 (R,R)-3,4,6-tri-o-benzoyl-1,2-o-propynylorthobenzoyl-α-D-galactopyranose
  参考文献：
  名称：

  Gold mediated glycosylations: selective activation of propargyl 1,2-orthoesters in the presence of aglycones containing a propargyl moiety

  摘要：

  在存在炔丙基糖苷和炔丙基醚的情况下，对炔丙基1,2-邻酯的选择性活化进行了研究；少量AuBr3催化剂可活化1,2-邻酯的炔丙氧基团，从而获得在还原端具有炔丙基团的双糖；此外，在反应条件下炔丙基醚不受影响。

  DOI：

  10.1039/b806707d

文献信息

• Facile synthesis of aminooxy glycosides by gold(III)-catalyzed glycosidation
  作者：Shivaji A. Thadke、Mahesh Neralkar、Srinivas Hotha

  DOI：10.1016/j.carres.2016.04.022

  日期：2016.7

  including glucosyl, mannosyl, galactosyl, ribofuranosyl, arabinofuranosyl, lyxofuranosyl and xylofuranosyl using gold catalysis repertoire. The protocol is identified to be compatible for the synthesis of aminooxy glycosides of higher oligosaccharides as well.

  据报道，在金（III）催化的糖苷化条件下，用各种醛糖衍生的炔丙基1,2-原酸酯对羟基琥珀酰亚胺和羟基邻苯二甲酰亚胺进行了O-糖基化。使用金催化库，由相应的糖基原酸酯，包括葡萄糖基，甘露糖基，半乳糖基，核呋喃糖基，阿拉伯呋喃糖基，莱呋喃呋喃糖基和木呋喃糖基，合成了多种羟基琥珀酰亚胺基和羟基邻苯二甲酰亚胺基糖苷。该方案经鉴定也可用于高级寡糖的氨基氧基糖苷的合成。
• Facile synthesis of unusual glycosyl carbamates and amino acid glycosides from propargyl 1,2-orthoesters as glycosyl donors
  作者：Ashif Y. Shaikh、Gopalsamy Sureshkumar、Debasish Pati、Sayam Sen Gupta、Srinivas Hotha

  DOI：10.1039/c1ob05056g

  日期：——

  Propargyl 1,2-O-orthoesters are exploited for the synthesis of 1,2-trans O-glycosides of protected amino acids. N-Fmoc- and N-Cbz protected serine/threonine - benzyl/methyl esters reacted well with glucosyl-, galactosyl-, mannosyl- and lactosyl- derived propargyl 1,2-orthoesters affording respective 1,2-transglycosides in good yields under AuBr3/4 Å MS Powder/CH2Cl2/rt. t-Boc serine derivative gave

  炔丙基1,2- O-原酸酯被用于合成被保护氨基酸的1,2-反式O-糖苷。N -Fmoc-和N -Cbz保护的丝氨酸/苏氨酸-苄基/甲酯与葡萄糖基，半乳糖基，甘露糖基和乳糖基衍生的炔丙基1,2-原酸酯反应良好，在较低的收率下提供各自的1,2-反式糖苷AuBr 3 /4ÅMS粉末/ CH 2 Cl 2 / rt。t -Boc丝氨酸衍生物可得到丝氨酸1,2-原酸酯和氨基甲酸糖基酯。优化的条件使得能够从N制备新的氨基甲酸酯糖基-Boc使用金催化剂和炔丙基1,2-原酸酯以优异的产率一步一步保护胺。
• Orthogonal Activation of Propargyl and <i>n</i>-Pentenyl Glycosides and 1,2-Orthoesters
  作者：Srinivasa Rao Vidadala、Shivaji A. Thadke、Srinivas Hotha

  DOI：10.1021/jo901837z

  日期：2009.12.4

  propargyl and n-pentenyl glycosides has been identified. According to this methodology, n-pentenyl glycosides can be selectively activated with NIS/TMSOTf in the presence of either armed or disarmed propargyl O-glycosides. In addition, we report herein that propargyl 1,2-orthoesters can be selectively activated with AuBr3 in CH2Cl2 at room temperature in the presence of n-pentenyl glycosides. Similarly

  已经确定了具有炔丙基和正戊烯基糖苷的正交激活策略。根据该方法，在有或无武装的炔丙基O-糖苷存在下，可以用NIS / TMSOTf选择性地活化正戊烯基糖苷。另外，我们在本文中报道，在正戊烯基糖苷存在下，在室温下可以在CH 2 Cl 2中用AuBr 3选择性地活化炔丙基1，2-原酸酯。类似地，在炔丙基糖苷存在的情况下，戊烯基1,2-原酸酯可以被NIS / Yb（OTf）3选择性活化。
• Preparation of propargyl 1,2-orthoesters of carbohydrates: From side reactions in dichloromethane to optimized reaction conditions in acetonitrile
  作者：Nicolas Jouandon、Jana Hammoud、Alexandre Touron、Laetitia Bailly、Alexandra Le Foll、Antoine Y.P. Joosten、Thomas Lecourt

  DOI：10.1016/j.carres.2022.108652

  日期：2022.11

  In this note, supercritical fluid chromatography coupled to high-resolution mass spectrometry (SFC-HRMS) has been used to identify a chloro glycoside formed during the preparation of propargyl 1,2-orthoesters in dichloromethane. Additional studies revealed that 20–40% of this side-product was obtained depending on the source of anhydrous solvent, and that tetrabutylammonium iodide amplifies this side-reaction

  在本说明中，超临界流体色谱与高分辨率质谱 (SFC-HRMS) 耦合已用于鉴定在二氯甲烷中制备炔丙基 1,2-原酸酯过程中形成的氯苷。其他研究表明，根据无水溶剂的来源，获得了 20-40% 的这种副产物，而四丁基碘化铵放大了这种副反应。最后，在乙腈中开发了一种可靠的方法，从甘露糖、葡萄糖和半乳糖系列中的过苯甲酰溴苷制备这些糖基供体，收率63-74 %。
• Propargyl 1,2-orthoesters as glycosyl donors: stereoselective synthesis of 1,2-trans glycosides and disaccharides
  作者：Gopalsamy Sureshkumar、Srinivas Hotha

  DOI：10.1016/j.tetlet.2007.07.015

  日期：2007.9

  Propargyl 1,2-orthoesters are identified as glycosyl donors. Various glycosides and disaccharides were synthesized in a stereoselective manner using AuBr3 as the promoter. AuBr3 may activate the alkyne resulting in the formation of a 1,2-dioxolenium ion and also behaves as a Lewis acid to facilitate the attack of the glycosyl acceptor. The versatility of the protocol was demonstrated using a panel of aglycones comprising aliphatic, alicyclic, steroidal and sugar alcohols. (C) 2007 Elsevier Ltd. All rights reserved.