Acetic acid (3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yl ester | 240415-47-8

• 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 (3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yl ester
• 英文别名: [(3R,4S,5S,6R)-2-methylidene-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 240415-47-8
• 化学式: C₃₀H₃₂O₆
• 分子量: 488.58
• InChiKey: YYERPWDQZZPOEE-IBHPWDLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  36
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Acetic acid (3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (3R,4R,5S,6R)-2-methylidene-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
  参考文献：
  名称：

  Selective radical synthesis of β- C -disaccharides

  摘要：

  Several P-C-disaccharides have been selectively synthesized by radical cyclization of two temporarily tethered functionalized monosaccharides. In this process, intramolecular addition of a carbohydrate-derived radical onto an anomeric exomethylene group, followed by axial hydrogen addition, resulted in beta stereochemistry. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)01533-7
• 作为产物：
  描述：

  2,3,5-三邻苄基-1-o-(4-硝基苯甲酰基)-d-阿拉伯呋喃糖 在 吡啶 、 溶剂黄146 作用下， 以 四氢呋喃 、 吡啶 、 水 为溶剂， 生成 Acetic acid (3R,4S,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methylene-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Selective radical synthesis of β- C -disaccharides

  摘要：

  Several P-C-disaccharides have been selectively synthesized by radical cyclization of two temporarily tethered functionalized monosaccharides. In this process, intramolecular addition of a carbohydrate-derived radical onto an anomeric exomethylene group, followed by axial hydrogen addition, resulted in beta stereochemistry. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(01)01533-7

文献信息

• Claisen-Ireland rearrangement: a new route to C-glycosides
  作者：Thierry Vidal、Arnaud Haudrechy、Yves Langlois

  DOI：10.1016/s0040-4039(99)01055-2

  日期：1999.7

  A Claisen-Ireland rearrangement led to the formation of C-glycan derivatives. Azidonitration-reduction or dihydroxylation afforded gluco- and galacto-derived β-C-glycosides. Subsequent deprotonation of bicyclic lactones 16 allowed the control of the newly created asymmetric centre.

  Claisen-Ireland重排导致C-聚糖衍生物的形成。叠氮化还原或二羟基化提供了葡萄糖和半乳糖衍生的β- C-糖苷。随后双环内酯16的去质子化使得可以控制新产生的不对称中心。