4'-methylbenzoyl 2,3,4,6-tetra-O-acetyl-β-D-selenoglucopyranoside | 869107-17-5

• 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-selenoglucopyranoside
• 英文别名: β-p-methylbenzoylselenoglycoside；(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((4-methylbenzoyl)selanyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate；1-Se-(4-methylbenzoyl)-2,3,4,6-tetra-O-acetyl-β-D-glucopyranose；[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(4-methylbenzoyl)selanyloxan-2-yl]methyl acetate
• CAS: 869107-17-5
• 化学式: C₂₂H₂₆O₁₀Se
• 分子量: 529.402
• InChiKey: MSHBQJIOAJRFFR-JPVHLGFFSA-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-selenoglucopyranoside 在 哌嗪 作用下， 以 N,N-二甲基甲酰胺 、 Petroleum ether 为溶剂， 生成 bis(1-deoxy-2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)diselenide
  参考文献：
  名称：

  CN116789719

  摘要：

  公开号：
• 作为产物：
  描述：

  2,3,4,6-四乙酰氧基-alpha-D-吡喃葡萄糖溴化物 在 三乙胺 作用下， 以 丙酮 、 乙腈 为溶剂， 生成 4'-methylbenzoyl 2,3,4,6-tetra-O-acetyl-β-D-selenoglucopyranoside
  参考文献：
  名称：

  使用异硒脲鎓盐作为糖基硒烯基转移试剂，可以方便地合成1,2-反式硒代糖苷。

  摘要：

  可以在一个高收率的步骤中从乙酰卤代糖制得的诸如三和四的Se-糖基-异亚硒酸铵盐被证明是用于合成多种硒代糖苷的方便的起始原料。与（芳）烷基卤化物的反应在温和的条件下，在室温下，在短时间内在室温下进行，以良好的收率得到相应的硒代糖苷。仅当芳族环上带有活化硝基时，芳基卤化物才会发生明显的反应。与酰化试剂如乙酸酐和苯甲酰氯的反应提供了端粒的硒酸酯，最近提出了其中的一些作为替代硒代糖苷合成的起始化合物。

  DOI：

  10.1016/j.carres.2012.07.012

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。
• 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。
• A Facile Method for β-Selenoglycoside Synthesis Using β-<i>p</i>-Methylbenzoyl Selenoglycoside as the Selenating Unit
  作者：Yumiko Kawai、Hiromune Ando、Hideya Ozeki、Mamoru Koketsu、Hideharu Ishihara

  DOI：10.1021/ol051804s

  日期：2005.10.1

  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.
• Convenient syntheses of 1,2-trans selenoglycosides using isoselenuronium salts as glycosylselenenyl transfer reagents
  作者：Ambati Ashok Kumar、Tünde Zita Illyés、Katalin E. Kövér、László Szilágyi

  DOI：10.1016/j.carres.2012.07.012

  日期：2012.10

  temperature to afford the corresponding selenoglycosides in good yields. Aryl halides react to appreciable extent only if bearing activating nitro groups on the aromatic ring. Reactions with acylating reagents such as acetic anhydride and benzoyl chlorides furnished anomeric selenoesters some of which were recently proposed as starting compounds for alternative selenoglycoside syntheses. Selenodisaccharides

  可以在一个高收率的步骤中从乙酰卤代糖制得的诸如三和四的Se-糖基-异亚硒酸铵盐被证明是用于合成多种硒代糖苷的方便的起始原料。与（芳）烷基卤化物的反应在温和的条件下，在室温下，在短时间内在室温下进行，以良好的收率得到相应的硒代糖苷。仅当芳族环上带有活化硝基时，芳基卤化物才会发生明显的反应。与酰化试剂如乙酸酐和苯甲酰氯的反应提供了端粒的硒酸酯，最近提出了其中的一些作为替代硒代糖苷合成的起始化合物。