(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((2-(methoxycarbonyl)phenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate | 112023-27-5

• 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: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((2-(methoxycarbonyl)phenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate
• 英文别名: 2-(methoxycarbonyl)phenyl 2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside；o-methoxycarbonylphenyl-2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside；2-(tetra-O-acetyl-β-D-glucopyranosylmercapto)-benzoic acid methyl ester；2-(Tetra-O-acetyl-β-D-glucopyranosylmercapto)-benzoesaeure-methylester；methyl 2-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylbenzoate
• CAS: 112023-27-5
• 化学式: C₂₂H₂₆O₁₁S
• 分子量: 498.508
• InChiKey: WJRNNDUELGGLJB-KQDNOMNESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  166
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((2-(methoxycarbonyl)phenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 5.0h， 生成 2-β-D-glucopyranosylmercapto-benzoic acid methyl ester
  参考文献：
  名称：

  Synthesis and absolute structures of Mycoplasma pneumoniae β-glyceroglycolipid antigens

  摘要：

  just recently, a pair of beta-glycolipids was isolated from the cell membrane of Mycoplasma pneumoniae as a mixture of the two compounds. They are the major immunodeterminants of this pathogenic Mycoplasma and indicate high medicinal potential. They have a beta-(1 -> 6)-linked disaccharide structure close to each other: one has beta-D-galactopyranoside (beta-Gal-type 1) at the non-reducing terminal, and another has beta-D-glucopyranoside (beta-Glc-type 2). In the present Study, the first stereoselective synthesis was conducted for each of the two beta-glycolipids 1 and 2. H-1 NMR and TLC-immunostaining studies of the synthetic compounds enable LIS to establish the absolute structures having the beta-(1 -> 6)-linked disaccharides at the glycerol sn-3 position. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2008.09.028
• 作为产物：
  描述：

  1-硫代-b-D-葡萄糖四乙酸酯 、 2-(methoxycarbonyl)benzenediazonium tetrafluoroborate 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 copper(l) chloride 作用下， 以 乙腈 为溶剂， 反应 0.08h， 以68%的产率得到(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-((2-(methoxycarbonyl)phenyl)thio)tetrahydro-2H-pyran-3,4,5-triyl triacetate
  参考文献：
  名称：

  在温和条件下铜 (I)-催化 Sandmeyer 型 S-芳基化 1-硫糖与芳基重氮盐

  摘要：

  在温和的反应条件下证明了通过S-芳基化从 1-硫糖制备S-芳基硫糖苷。在氯化铜 (I) 和 DBU 存在下，衍生自葡萄糖、氨基葡萄糖、半乳糖、甘露糖、核糖、麦芽糖和乳糖的多种受保护和未受保护的 1-硫糖与官能化芳基重氮盐发生交叉偶联反应。在 5 分钟内以 55-88% 的收率获得所需的产品。在标准反应条件下可以耐受各种官能团，包括卤素。证明了生物学相关的抗糖尿病药 dapagliflozin S -类似物和熊果苷S -类似物（酪氨酸酶抑制剂）的合成。

  DOI：

  10.1021/acs.joc.2c00930

文献信息

• Diversity-oriented synthesis of fused thioglycosyl benzo[e][1,4]oxathiepin-5-ones and benzo[f][1,4]thiazepin-5(2H)-ones by a sequence of palladium-catalyzed glycosyl thiol arylation and deprotection–lactonization reactions
  作者：Riyadh Ahmed Atto AL-Shuaeeb、Gilles Galvani、Guillaume Bernadat、Jean-Daniel Brion、Mouad Alami、Samir Messaoudi

  DOI：10.1039/c5ob01603g

  日期：——

  An efficient synthesis of thioglycosylated benzo[e][1,4]oxathiepin-5-one and benzothiazepinone derivatives by a sequence of palladium-catalyzed glycosyl thiol arylation followed by deprotection–lactonization reactions has been reported. This diversity-oriented strategy enabled access to unknown complex cyclic scaffolds with polyhydroxylated appendages of biological interest.

  据报道，通过一系列钯催化的糖基硫醇芳基化反应，然后进行脱保护-内酯化反应，可以有效合成硫糖基化的苯并[ e ] [1,4]草硫平-5-酮和苯并噻唑酮酮衍生物。这种以多样性为导向的策略使人们能够利用具有生物兴趣的多羟基化附属物访问未知的复杂环状支架。
• Über die Synthese von S-β-D-Glucopyranosiden verschiedener Derivate der 2-Mercaptobenzoesäure (Thiosalicylsäure) 6. Mitteilung „Über Phenolglykoside”
  作者：Günther Wagner

  DOI：10.1002/ardp.19572901005

  日期：——
• Evaluating the reactivity and stereoselectivity of salicyl-type thioglycosides as non-malodorous thioglycoside alternatives for oligosaccharide synthesis
  作者：Hirofumi Dohi、Risa Sakurai、Manami Tamura、Ryota Komai、Yoshihiro Nishida

  DOI：10.1080/07328303.2021.1921787

  日期：2021.3.31