| 166887-16-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• CAS: 166887-16-7
• 化学式: C₁₀H₁₆O₅
• 分子量: 216.234
• InChiKey: GZACVTXTOGDVKI-BZNPZCIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.38
• 重原子数：
  15.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  在 吡啶 、 sodium carbonate 、 氟化氢吡啶 、 红铝 作用下， 以 二氯甲烷 为溶剂， 反应 22.08h， 生成 (R)-4-((3aR,5R,6S,6aR)-5-Hydroxymethyl-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yloxy)-azetidin-2-one
  参考文献：
  名称：

  Asymmetric induction in [2+2]cycloaddition of chlorosulfonyl isocyanate to 1,2-O-isopropylidene-3-O-vinyl-glycofuranoses

  摘要：

  The asymmetric [2+2]cycloaddition of chlorosulfonyl isocyanate to 1,2-O-isopropylidene-3-O-vinylglycofuranoses is presented. Bulky substituent at the C-4 carbon atom promotes excellent stereoselectivity affording (R) configuration at the C-4' carbon atom of the azetidinone ring. Intramolecular cyclization in compounds 9 or 12 provides diastereomeric cephem 20 and 21.

  DOI：

  10.1016/s0957-4166(00)86293-x
• 作为产物：
  描述：

  1,2-O-isopropylidene-5-O-tosyl-3-O-vinyl-α-D-xylofuranose 在 氨 、 sodium 作用下， 以 四氢呋喃 为溶剂， 反应 1.5h， 以76%的产率得到
  参考文献：
  名称：

  Asymmetric induction in [2+2]cycloaddition of chlorosulfonyl isocyanate to 1,2-O-isopropylidene-3-O-vinyl-glycofuranoses

  摘要：

  The asymmetric [2+2]cycloaddition of chlorosulfonyl isocyanate to 1,2-O-isopropylidene-3-O-vinylglycofuranoses is presented. Bulky substituent at the C-4 carbon atom promotes excellent stereoselectivity affording (R) configuration at the C-4' carbon atom of the azetidinone ring. Intramolecular cyclization in compounds 9 or 12 provides diastereomeric cephem 20 and 21.

  DOI：

  10.1016/s0957-4166(00)86293-x

文献信息

• Reductive opening of carbohydrate phenylsulfonylethylidene (PSE) acetals
  作者：Florence Chéry、Elena Cabianca、Arnaud Tatibouët、Ottorino De Lucchi、Thisbe K. Lindhorst、Patrick Rollin

  DOI：10.1016/j.carres.2015.09.011

  日期：2015.11

  carbohydrate-derived phenylsulfonylethylidene (PSE) acetals show a different behavior in reductive desulfonylation than simple symmetrical acetals. Here we have investigated various SET-type reaction conditions in order to open PSE acetals regioselectively and to produce chiral omega-hydroxyethenyl ethers. Whereas sodium amalgam leads to a mixture of regioisomeric vinyl ethers besides the ethylidene acetal, samarium

  苯磺酰基亚乙基（PSE）缩醛在碳水化合物化学中是一个相对较新的保护基。但是，碳水化合物衍生的苯磺酰亚乙基（PSE）缩醛在还原性脱磺酰基反应中的行为与简单的对称缩醛不同。在这里，我们研究了各种SET型反应条件，以选择性地打开PSE缩醛并生产手性ω-羟基乙烯基醚。汞齐除亚乙缩醛外还产生了区域异构乙烯基醚的混合物，而碘化for则适合于区域选择性的开环。用七个不同的碳水化合物PSE乙缩醛（分别为1,3-二氧杂环己烷和1,3-二氧戊环类型）显示。
• A simple one-pot entry to cyclic ethers of varied ring sizes from diols via phosphonium ion induced iodination and base catalyzed Williamson etherification
  作者：Biswajit Gopal Roy、Ashim Roy、Basudeb Achari、Sukhendu B. Mandal

  DOI：10.1016/j.tetlet.2006.08.090

  日期：2006.10

  A novel and an efficient one-pot cyclization method using triphenylphosphine, iodine and a nitrogenous base has been established for the synthesis of cyclic ethers of various ring sizes. This appears to follow a two-step procedure, which includes preferential substitution of one hydroxyl group by an iodide generated in situ followed by an intramolecular ring closure through the attack of a free hydroxyl

  已经建立了使用三苯基膦，碘和含氮碱的新颖且有效的一锅环化方法，用于合成各种环大小的环醚。这似乎遵循两步程序，其中包括一个羟基被原位生成的碘优先取代，然后通过游离羟基或更多亲核性氧化物离子的攻击而分子内闭环。
• Optimized Synthesis of Vinyl Ether Sugars and Vinyl Glycosides through Transfer Vinylation Catalyzed by (4,7‐Ph₂‐phen)Pd(OOCCF₃)₂
  作者：Martin Bosch、Sean Handerson、Marcel Schlaf

  DOI：10.1080/07328300802030852

  日期：2008.5

  Sugar vinyl ethers and vinyl glycosides are conveniently synthesized by catalytic transfer vinylation with butyl vinyl ether, which serves as both the solvent and source of vinyl. The air-stable catalyst (4,7-diphenyl-1,10-phenanthroline)Pd(OOCCF(3))(2) is prepared in situ from commercially available components.