cyclopropylmethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside | 168072-52-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: cyclopropylmethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
• 英文别名: cycloproylmethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythrohex-2-enopyranoside；[(2R,3S,6S)-3-acetyloxy-6-(cyclopropylmethoxy)-3,6-dihydro-2H-pyran-2-yl]methyl acetate
• CAS: 168072-52-4
• 化学式: C₁₄H₂₀O₆
• 分子量: 284.309
• InChiKey: AGPJLSFMZBKGCV-MJBXVCDLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  20
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  71.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  cyclopropylmethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside 在 sodium periodate 、 cerium(III) chloride heptahydrate 作用下， 以 水 、 乙酸乙酯 为溶剂， 以96%的产率得到
  参考文献：
  名称：

  “One-pot” access to α-d-mannopyranosides from glycals employing ruthenium catalysis

  摘要：

  描述了一种从甘露糖环糖制备α-d-甘露聚糖的高效便捷的一锅法方法。

  DOI：

  10.1039/c4ra08241a
• 作为产物：
  描述：

  羟甲基环丙烷 、 乙酰化葡萄烯糖 在 montmorillonite K-10 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以87%的产率得到cyclopropylmethyl 4,6-di-O-acetyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  通过费里尔重排合成新的2,3-不饱和O-糖苷1

  摘要：

  据报道，利用费瑞尔的重排和不同的催化剂，合成了五个新的2,3-不饱和的O-糖苷（3a-e）。

  DOI：

  10.1081/car-100108274

文献信息

• Ceric(iv) ammonium nitrate-catalyzed glycosidation of glycals: a facile synthesis of 2,3-unsaturated glycosides
  作者：Jhillu S. Yadav、Basi V. Subba Reddy、Sushil Kumar Pandey

  DOI：10.1039/b009973m

  日期：——

  Glycosidation of glycals with alcohols in the presence of a catalytic amount of ceric(IV) ammonium nitrate under neutral conditions proceeds smoothly in refluxing acetonitrile to afford the corresponding 2,3-unsaturated glycosides in excellent yields.

  在温和条件下，以催化量的硝酸铈铵作为催化剂，糖酸内酯与醇在回流的乙腈中进行甘露糖基化反应，能够高效地生成相应的2,3-不饱和糖苷。
• Iron(III) triflate, a new efficient catalyst for Type I Ferrier Rearrangement
  作者：Peiran Chen、Shaoshan Wang

  DOI：10.1016/j.tet.2012.04.115

  日期：2012.7

  By using iron(III) triflate as catalyst, an improved method for the synthesis of 2,3-unsaturated-O-glycosides has been established. A series of 2,3-unsaturated-O-glucosides were obtained from 2,4,6-tri-O-acetyl-d-glucal in good yield and high anomeric selectivity.

  通过使用三氟甲磺酸铁（III）作为催化剂，已经建立了一种合成2,3-不饱和-O-糖苷的改进方法。一系列的2,3-unsaturated- ö从获得-glucosides -2,4,6-三ö乙酰基d -glucal以良好的收率和高的异头选择性。
• Synthesis of new branched-chain amino sugars
  作者：João R de Freitas Filho、Rajendra M Srivastava、Waldenberg J.P da Silva、Louis Cottier、Denis Sinou

  DOI：10.1016/s0008-6215(02)00527-x

  日期：2003.3

  1,3-Dipolar cycloaddition of methylideneaniline N-oxide to sugar enones is described. The addition occurred exclusively from the side opposite to the aglycone affording the corresponding alkyl alpha-D-lyxo-hexopyranosid-(2,3:5',4')-phenylisoxazolidin-4-uloses. Hydrogenation of these compounds readily yielded the corresponding alkyl 3-deoxy-3-N-phenylaminomethyl-alpha-D-talopyranoside, that were readily

  描述了亚甲基苯胺N-氧化物与糖烯酮的1，3-偶极环加成。该加成仅从糖苷配基的相反侧发生，得到相应的烷基α-D-lyxo-己吡喃糖苷-（2,3：5'，4'）-苯基异恶唑烷丁-4-ulose。这些化合物的氢化容易产生相应的烷基3-脱氧-3-N-苯基氨基甲基-α-D-塔洛吡喃糖苷，其易于转化为乙酸酯。通过1 H NMR研究和使用AM1方法的半经验分子轨道计算，确定了双环化合物的结构和构象。
• Copper(II) Triflate as a Mild and Efficient Catalyst for Ferrier Glycosylation: Synthesis of 2,3-Unsaturated O-Glycosides
  作者：Palakodety Radha Krishna、Sudhir Kashyap、Batthula Srinivas、Thurpu Reddy

  DOI：10.1055/s-0033-1341232

  日期：——

  Various acceptors including carbohydrates, amino acids, natural products, and hydroxylamine derivatives were coupled with 3,4,6-tri-O-acetyl-d-glucal in the presence of Cu(OTf)(2) as catalyst. The protocol offers facile and efficient Ferrier glycosylation for the synthesis of 2,3-unsaturaed O-glycosides in good yields and high anomeric selectivity.
• An efficient procedure for the synthesis of 2,3-unsaturated-O-glycosides: TiCl3(OTf) as the catalyst for type I Ferrier rearrangement
  作者：Peiran Chen、Lei Lin

  DOI：10.1016/j.tet.2013.04.051

  日期：2013.6

  An efficient type I Ferrier rearrangement reaction system for the synthesis of 2,3-unsaturated-O-glycosides has been established by using TiCl3(OTf) as the catalyst. A series of 2,3-unsaturated-O-glucosides were prepared from 3,4,6-tri-O-acetyl-D-glucal in good yield and high anomeric selectivity. (C) 2013 Elsevier Ltd. All rights reserved.