para-trifuoromethylphenyl 4,6-di-O-acetyl-2,3-dideoxy-erythro-hex-2-eno-1-thio-α-D-pyranoside | 1632129-92-0

• 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: para-trifuoromethylphenyl 4,6-di-O-acetyl-2,3-dideoxy-erythro-hex-2-eno-1-thio-α-D-pyranoside
• 英文别名: [(2R,3S,6R)-3-acetyloxy-6-[4-(trifluoromethyl)phenyl]sulfanyl-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 1632129-92-0
• 化学式: C₁₇H₁₇F₃O₅S
• 分子量: 390.38
• InChiKey: SKMVQVZYEVRUCM-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  26
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  87.1
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  4-(三氟甲基)苯硫酚 、 乙酰化葡萄烯糖 在 copper(II) bis(trifluoromethanesulfonate) 作用下， 以 乙腈 为溶剂， 反应 2.0h， 以76%的产率得到para-trifuoromethylphenyl 4,6-di-O-acetyl-2,3-dideoxy-erythro-hex-2-eno-1-thio-α-D-pyranoside
  参考文献：
  名称：

  Copper(II) Triflate as a Mild and Efficient Catalyst for Ferrier Glycosylation: Synthesis of 2,3-Unsaturated O-Glycosides

  摘要：

  Various acceptors including carbohydrates, amino acids, natural products, and hydroxylamine derivatives were coupled with 3,4,6-tri-O-acetyl-d-glucal in the presence of Cu(OTf)(2) as catalyst. The protocol offers facile and efficient Ferrier glycosylation for the synthesis of 2,3-unsaturaed O-glycosides in good yields and high anomeric selectivity.

  DOI：

  10.1055/s-0033-1341232

文献信息

• Diastereoselective Synthesis of Thioglycosides via Pd-Catalyzed Allylic Rearrangement
  作者：Jiagen Li、Ming Wang、Xuefeng Jiang

  DOI：10.1021/acs.orglett.1c03302

  日期：2021.12.3

  palladium-catalyzed allylic rearrangement yields various substituents on α-isomer thioglycosides. Two comprehensive series of aryl and benzyl thioglycosides were obtained via a combination of thiosulfates with glycals derived from glucose, arabinose, galactose, and rhamnose. Furthermore, diosgenyl α-l-rhamnoside and isoquercitrin achieved selectivity via stereospecific [2,3]-sigma rearrangements of α-sulfoxide-rhamnoside

  立体选择性糖基化在碳水化合物化学中具有挑战性。在此，通过钯催化的烯丙基重排对糖醛进行立体选择性硫代糖基化，可在 α-异构体硫糖苷上产生各种取代基。通过硫代硫酸盐与衍生自葡萄糖、阿拉伯糖、半乳糖和鼠李糖的糖苷的组合，获得了两个综合系列的芳基和苄基硫糖苷。此外，薯蓣基 α-l-鼠李糖苷和异槲皮苷分别通过 α-亚砜-鼠李糖苷和 α-亚砜-葡萄糖苷的立体特异性 [2,3]-σ 重排实现了选择性。
• 不饱和硫苷化合物及其选择性合成方法与应用
  申请人：华东师范大学

  公开号：CN113651863A

  公开（公告）日：2021-11-16

  本发明公开了一种选择性合成式(II)α‑硫苷化合物、式(III)β‑硫苷化合物的合成方法，在反应溶剂中，以三乙酰葡萄糖烯为反应原料，以不同取代基的有机硫代硫酸盐为硫源，在金属钯盐、配体的作用下，选择性合成α‑硫苷化合物(II)、β‑硫苷化合物(III)。本发明所述的合成方法，原料易得价廉，反应操作简单，反应条件温和，产率较高，官能团耐受优秀。本发明实现了一些复杂分子的合成与修饰，为药物化学的研究提供了选择性构建含有不饱和键硫苷化合物的高效方法。
• Ruthenium Catalyzed Stereo/Chemo/Regioselective One-Pot Synthesis of C(2)–C(3) Unsaturated and α-<scp>d</scp>-Mannopyranosyl Sulfones
  作者：Sravanthi Chittela、Thurpu Raghavender Reddy、Palakodety Radha Krishna、Sudhir Kashyap

  DOI：10.1021/acs.joc.5b00975

  日期：2015.7.17

  An efficient and divergent approach to C(2)-C(3) unsaturated glycosyl and a-p-mannopyranosyl sulfones has been developed via ruthenium-promoted direct glycosylation, oxidation, and dihydroxylation from glycal in one-pot. The presence of stoichiometric amounts of NaIO4 and in situ generation of RuO4 from a RuCl3-NaIO4 reagent system were crucial for chemoselective oxidation of sulfide in the presence of an olefin moiety. The dual-role of ruthenium in sequential glycosylation-oxidation-dihydroxylation is amenable to a wide range of thio acceptors to access alpha-n-mannopyranosyl sulfones in good yields with high regioselectivity.
• Zn(OTf)2-Catalyzed Glycosylation of Glycals: Synthesis of 2,3-Unsaturated Glycosides via a Ferrier Reaction
  作者：Palakodety Radha Krishna、Sudhir Kashyap、Gundeboina Narasimha、Batthula Srinivas

  DOI：10.1055/s-0033-1340552

  日期：——

  A mild, catalytic, and efficient protocol has been developed for the synthesis of 2,3-unsaturated glycosides or pseudo-glycals' using Zn(OTf)(2). Stereoselective glycosylation of glycal donor with various acceptors comprising of alcohols, phenols, thiols, and sugar aglycones proceeds smoothly to afford the corresponding 2,3-unsaturaed glycosides in good to excellent yields.