Acetic acid (2R,3S,4R)-4-hydroxy-2-(toluene-4-sulfonyloxymethyl)-3,4-dihydro-2H-pyran-3-yl ester | 142866-02-2

• 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: Acetic acid (2R,3S,4R)-4-hydroxy-2-(toluene-4-sulfonyloxymethyl)-3,4-dihydro-2H-pyran-3-yl ester
• 英文别名: [(2R,3S,4R)-4-hydroxy-2-[(4-methylphenyl)sulfonyloxymethyl]-3,4-dihydro-2H-pyran-3-yl] acetate
• CAS: 142866-02-2
• 化学式: C₁₅H₁₈O₇S
• 分子量: 342.37
• InChiKey: HJYKZAWCGSWJMJ-KFWWJZLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  108
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3S,4R)-4-hydroxy-2-(toluene-4-sulfonyloxymethyl)-3,4-dihydro-2H-pyran-3-yl ester 在 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 triethylamine tris(hydrogen fluoride) 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 0.25h， 生成
  参考文献：
  名称：

  Synthesis of C-D-E trisaccharide precursors of olivomycin A.

  摘要：

  Syntheses of functionalized C-D-E trisaccharide precursors (16, 5) of olivomycin A are reported. A stereoselective C-D beta-glycosidation was accomplished by employing 2-deoxy-2-(phenylthio)-alpha-glucotrichloro-acetimidate 8. The alpha-D-E glycosidic linkage was introduced by using 2-deoxy-2-iodo-alpha-glycosyl acetate donor 14 as the glycosyl transfer agent.

  DOI：

  10.1021/jo00044a010
• 作为产物：
  描述：

  4-O-Acetyl-3-O-tert-butyldimethylsilyl-6-O-tosyl-D-glucal 在 triethylamine tris(hydrogen fluoride) 作用下， 以 乙腈 为溶剂， 以75%的产率得到Acetic acid (2R,3S,4R)-4-hydroxy-2-(toluene-4-sulfonyloxymethyl)-3,4-dihydro-2H-pyran-3-yl ester
  参考文献：
  名称：

  Synthesis of C-D-E trisaccharide precursors of olivomycin A.

  摘要：

  Syntheses of functionalized C-D-E trisaccharide precursors (16, 5) of olivomycin A are reported. A stereoselective C-D beta-glycosidation was accomplished by employing 2-deoxy-2-(phenylthio)-alpha-glucotrichloro-acetimidate 8. The alpha-D-E glycosidic linkage was introduced by using 2-deoxy-2-iodo-alpha-glycosyl acetate donor 14 as the glycosyl transfer agent.

  DOI：

  10.1021/jo00044a010

文献信息

• Total Synthesis of Formamicin
  作者：Timothy B. Durham、Nicolas Blanchard、Brad M. Savall、Noel A. Powell、William R. Roush

  DOI：10.1021/ja048493l

  日期：2004.8.1

  enantioselective total synthesis of the cytotoxic plecomacrolide natural product formamicin (1) is described. Key aspects of this synthesis include the efficient transacetalation reactions of MOM ethers 28 and 38 to form the seven-membered formyl acetals 29 and 39, a late-stage Suzuki cross-coupling reaction of the highly functionalized vinyl boronic acid 6 and vinyl iodide 7, a highly beta-selective

  描述了细胞毒性 plecomacrolide 天然产物甲霉素 (1) 的对映选择性全合成。该合成的关键方面包括 MOM 醚 28 和 38 的有效转缩醛反应以形成七元甲酰缩醛 29 和 39，高度官能化乙烯基硼酸 6 和乙烯基碘化物 7 的后期 Suzuki 交叉偶联反应， β-羟基酮 4 与 2,6-二脱氧-2-碘吡喃葡萄糖基氟 3 的高度β-选择性糖苷化反应，以及由原位生成的 Et(3)N.2HF 介导的倒数第二中间体 77 的全局脱甲硅烷基化反应。
• 2-Deoxy-2-iodo-α-mannopyranosyl and -talopyranosyl Acetates:  Highly Stereoselective Glycosyl Donors for the Synthesis of 2-Deoxy-α-glycosides
  作者：William R. Roush、Sridhar Narayan

  DOI：10.1021/ol9908068

  日期：1999.9.1

  [formula: see text] TMS-OTf- or TBS-OTf-promoted glycosidation reactions of 2-deoxy-2-iodo-alpha-mannopyranosyl acetates 8-10 and the 2-deoxy-2-iodo-alpha-talopyranosyl acetate 11 provide the corresponding 2-deoxy-2-iodo-alpha-pyranosides, precursors to 2-deoxy-alpha-glycosides, as the only observed reaction products.

  [分子式：见正文]由TMS-OTf或TBS-OTf促进的乙酸2-脱氧-2-碘-α-甘露吡喃糖基乙酸酯8-10和2-脱氧-2-碘-α-戊吡喃糖基乙酸酯11的糖基化反应相应的2-脱氧-2-碘-α-吡喃糖苷（2-脱氧α-糖苷的前体）是唯一观察到的反应产物。
• Stereoselective synthesis of 2-deoxy-β-glycosides from glycal precursors. 2. Stereochemistry of glycosidation reactions of 2-thiophenyl- and 2-selenophenyl-α-d-gluco-pyranosyl donors
  作者：William R. Roush、David P. Sebesta、Ray A. James

  DOI：10.1016/s0040-4020(97)90395-1

  日期：1997.6

  configurationally stable (at C(2)). The main problem with imidates 11 is that the stereoselectivity of their reactions with alcohols is substrate dependent, with best selectivity for the desired β-glycosides 35 and 42 being obtained with the least sterically hindered alcohols. The fact that the α-glycosides 36 and 43 comprise up to 20–50% of the product in glycosidation reactions of hindered secondary

  我们已经证明了4-O-乙酰基-6-溴-3-O-（叔丁基二甲基甲硅烷基）-2-脱氧-2-硫代苯基-1-三氯乙酰胺基-α-d-吡喃葡萄糖11b是最有效和选择性的供体用于所考察的一系列糖基供体的2-脱氧-β-糖苷的合成。不同于2-硒吩基取代的供体8，其被证明是下标TMS-光学传递函数构型上不稳定的促进糖基化的条件下，从而产生α甘露糖苷14，17和20从β葡糖供体8，2-噻吩基取代的供体9和11似乎是完全配置稳定（在C（2））。酰亚胺的主要问题由图11可知，它们与醇的反应的立体选择性取决于底物，而对所期望的β-糖苷35和42的最佳选择性是由受阻最少的醇获得的。在受阻仲醇的糖基化反应中，α-糖苷36和43最多占产物的20-50％，这一事实支持了以下观点：反应立体选择性不受epi硫离子（47和47'）的中间性支配，而是氧离子46及其构象上的反相异构体46'的取代反应起主要作用。
• 2-Deoxy-2-iodo-β-glucopyranosyl Fluorides:  Mild and Highly Stereoselective Glycosyl Donors for the Synthesis of 2-Deoxy-β-glycosides from β-Hydroxy Ketones
  作者：Nicolas Blanchard、William R. Roush

  DOI：10.1021/ol027257h

  日期：2003.1.1

  2-Deoxy-2-iodo-beta-glucopyranosyl fluoride 14 is a highly stereoselective glucopyranosyl donor that may be activated under mild conditions. Application of this new glycosyl donor to the glycosidation reactions of a variety of acceptors including beta-hydroxy ketones affords beta-glycosides with high efficiency and stereoselectivity.
• A Highly Stereoselective Synthesis of 2-Deoxy-β-glycosides Using 2-Deoxy-2-iodo-glucopyranosyl Acetate Donors
  作者：William R. Roush、Chad E. Bennett

  DOI：10.1021/ja984365j

  日期：1999.4.1