4'-methylbenzoyl 2,3,4,6-tetra-O-acetyl-β-D-selenogalactopyranoside | 869107-34-6

• 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: 4'-methylbenzoyl 2,3,4,6-tetra-O-acetyl-β-D-selenogalactopyranoside
• 英文别名: p-methylbenzoyl 2,3,4,6-tetra-O-acetyl-1-seleno-β-D-galactopyranoside；2,3,4,6-tetra-O-acetyl-1-Se-p-toluoyl-β-D-selenogalactopyranose；[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(4-methylbenzoyl)selanyloxan-2-yl]methyl acetate
• CAS: 869107-34-6
• 化学式: C₂₂H₂₆O₁₀Se
• 分子量: 529.402
• InChiKey: MSHBQJIOAJRFFR-QWPXSNKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.92
• 重原子数：
  33
• 可旋转键数：
  12
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  4'-methylbenzoyl 2,3,4,6-tetra-O-acetyl-β-D-selenogalactopyranoside 在 哌嗪 、 caesium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.17h， 以100%的产率得到bis-1-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl) diselenide
  参考文献：
  名称：

  A Facile Method for β-Selenoglycoside Synthesis Using β-p-Methylbenzoyl Selenoglycoside as the Selenating Unit

  摘要：

  The reaction between alpha-glycosyl bromides and potassium p-methylselenobenzoate yields beta-p-methylbenzoyl selenoglycosides. The acyl selenoglycosides were activated by the action of a secondary amine and CS2CO3 to produce an anomeric selenolate anion, which reacted in situ with various electrophiles to yield novel selenoglycosides while retaining the anomeric stereochemistry.

  DOI：

  10.1021/ol051804s
• 作为产物：
  描述：

  对甲基苯甲酰氯 在 氢氧化钾 、 selenium 、 sodium tetrahydroborate 、 n-Bu₄HSO₄ 、 sodium carbonate 作用下， 以 甲醇 、 乙醇 、 乙酸乙酯 为溶剂， 反应 4.08h， 生成 4'-methylbenzoyl 2,3,4,6-tetra-O-acetyl-β-D-selenogalactopyranoside
  参考文献：
  名称：

  A Facile Method for β-Selenoglycoside Synthesis Using β-p-Methylbenzoyl Selenoglycoside as the Selenating Unit

  摘要：

  The reaction between alpha-glycosyl bromides and potassium p-methylselenobenzoate yields beta-p-methylbenzoyl selenoglycosides. The acyl selenoglycosides were activated by the action of a secondary amine and CS2CO3 to produce an anomeric selenolate anion, which reacted in situ with various electrophiles to yield novel selenoglycosides while retaining the anomeric stereochemistry.

  DOI：

  10.1021/ol051804s

文献信息

• Room-Temperature Pd-Catalyzed Synthesis of 1-(Hetero)aryl Selenoglycosides
  作者：Mingxiang Zhu、Mouad Alami、Samir Messaoudi

  DOI：10.1021/acs.orglett.0c02352

  日期：2020.8.21

  A general protocol for functionalization of an anomeric selonate anion at room temperature has been reported. By using the PdG3 XantPhos catalyst, the cross-coupling between the in situ-generated glycosyl selenolate and a broad range of (hetero)aryl and alkenyl iodides furnished a series of functionalized selenoglycosides in excellent yields with perfect control of the anomeric configuration.

  已经报道了在室温下官能化异头亚硒酸根阴离子的一般方案。通过使用PdG3 XantPhos催化剂，原位生成的糖基硒烯酸酯与各种（杂）芳基和烯基碘化物之间的交叉偶联以优异的收率提供了一系列官能化的硒代糖苷，并完美地控制了端基异构体构型。
• Modular Synthesis of Aryl Thio/Selenoglycosides via the Catellani Strategy
  作者：Ya-Nan Ding、Yan-Chong Huang、Wei-Yu Shi、Nian Zheng、Cui-Tian Wang、Xi Chen、Yang An、Zhe Zhang、Yong-Min Liang

  DOI：10.1021/acs.orglett.1c01723

  日期：2021.8.6

  We described a novel palladium-catalyzed domino procedure for the preparation of (hetero)aryl thio/selenoglycosides. Readily available (hetero)aryl iodides and easily accessible 1-thiosugars/1-selenosugars are utilized as the substrates. Meanwhile, 10 types of sugars are quite compatible with this reaction with good regio- and stereoselectivity, high efficiency, and broad applicability (up to 89%,

  我们描述了一种用于制备（杂）芳基硫代/硒糖苷的新型钯催化多米诺骨牌程序。容易获得的（杂）芳基碘化物和容易获得的 1-硫糖/1-硒糖被用作底物。同时，10种糖类与该反应相容，具有良好的区域选择性和立体选择性、高效率和广泛的适用性（高达89%，53例）。该方法能够直接形成（杂）芳基硫代/硒糖苷的 C(sp 2 )–S/Se 键。
• Lewis Acid Induced Anomerization of <i>Se</i>-Glycosides. Application to Synthesis of α-<i>Se</i>-GalCer
  作者：Anthony W. McDonagh、Mary F. Mahon、Paul V. Murphy

  DOI：10.1021/acs.orglett.5b03591

  日期：2016.2.5

  galacturonic acid derivatives is reported. The reaction was successful for galacturonic acid when various alkyl, alkenyl, alkynyl, saccharide, steroid, and lipid groups were attached to the anomeric Se atom. An increased amount of TiCl4 and/or higher temperature were needed to ensure completion of the reaction in some cases. Yields were higher for reactions carried out at higher dilution. The reaction was applied

  报道了TiCl 4诱导的半乳糖醛酸衍生物的硒糖苷的异构化。当各种烷基，烯基，炔基，糖，类固醇和脂质基团连接到异头硒原子上时，该反应对于半乳糖醛酸是成功的。在某些情况下，需要增加TiCl 4的量和/或更高的温度以确保反应完成。在较高稀释度下进行的反应的产率较高。该反应用于强力免疫刺激剂α-GalCer（KRN7000）的Se基模拟物的合成。
• Stereoselective synthesis of various α-selenoglycosides using in situ production of α-selenolate anion
  作者：Masahiro Nanami、Hiromune Ando、Yumiko Kawai、Mamoru Koketsu、Hideharu Ishihara

  DOI：10.1016/j.tetlet.2006.12.056

  日期：2007.2

  alkyl and aryl selenoglycosides, selenoglycosyl amino acid and selenodisaccharide have been synthesized in a stereoselective manner. The key precursor of α-anomeric selenolate anion was designed as p-methylbenzoyl selenoglycoside, which was synthesized by the reaction of β-glycosyl chloride with potassium p-methylselenobenzoate. Upon the action of piperazine or methylhydrazine in the presence of Cs2CO3

  已经以立体选择的方式合成了多种α-硒代糖苷，包括烷基和芳基硒代糖苷，硒代糖基氨基酸和亚硒二糖。α异头selenolate阴离子的关键前体被设计为p -methylbenzoyl selenoglycoside，其通过β-糖基氯与钾反应，合成p -methylselenobenzoate。在Cs 2 CO 3的存在下，哌嗪或甲基肼的作用下，酰基硒代糖苷产生异头型硒酸根阴离子，其与各种亲电子部分原位反应生成α-硒代糖苷。
• Expanded potential of seleno-carbohydrates as a molecular tool for X-ray structural determination of a carbohydrate–protein complex with single/multi-wavelength anomalous dispersion phasing
  作者：Tatsuya Suzuki、Hisayoshi Makyio、Hiromune Ando、Naoko Komura、Masanori Menjo、Yusuke Yamada、Akihiro Imamura、Hideharu Ishida、Soichi Wakatsuki、Ryuichi Kato、Makoto Kiso

  DOI：10.1016/j.bmc.2014.02.023

  日期：2014.4

  Seleno-lactoses have been successfully synthesized as candidates for mimicking carbohydrate ligands for human galectin-9 N-terminal carbohydrate recognition domain (NCRD). Selenium was introduced into the mono-or di-saccharides using p-methylselenobenzoic anhydride (Tol(2)Se) as a novel selenating reagent. The TolSe-substituted monosaccharides were converted into selenoglycosyl donors or acceptors, which were reacted with coupling partners to afford seleno-lactoses. The seleno-lactoses were converted to the target compounds. The structure of human galectin-9 NCRD co-crystallized with 6-MeSe-lactose was determined with single/multi-wavelength anomalous dispersion (SAD/MAD) phasing and was similar to that of the co-crystal with natural lactose. (C) 2014 Elsevier Ltd. All rights reserved.