benzyl 2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-α-L-rhamnopyranoside | 83866-15-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-α-L-rhamnopyranoside
• 英文别名: benzyl 2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl-(1->4)-2,3-di-O-isopropylidene-α-L-rhamnopyranoside；(3aR,4R,6S,7S,7aR)-2,2,6-trimethyl-4-phenylmethoxy-7-[(2R,3S,4S,5R,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran
• CAS: 83866-15-3
• 化学式: C₅₀H₅₆O₁₀
• 分子量: 816.989
• InChiKey: MWSOTJMKLQPNJT-OWADPKIYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  60
• 可旋转键数：
  18
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  92.3
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  2,3,4,6-tetra-O-benzyl-D-mannopyranose 在 molecular sieve 、 sodium hydride 、 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 54.0h， 生成 benzyl 2,3-O-isopropylidene-4-O-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl)-α-L-rhamnopyranoside
  参考文献：
  名称：

  Retention of the anomeric configuration in the imidate procedure: synthesis of disaccharides containing α-l-rhamnopyranosyl and α-d-mannopyranosyl groups

  摘要：

  DOI：

  10.1016/s0008-6215(00)80788-0

文献信息

• Cationic Palladium(II)-Catalyzed Stereoselective Glycosylation with Glycosyl Trichloroacetimidates
  作者：Jaemoon Yang、Colleen Cooper-Vanosdell、Enoch A. Mensah、Hien M. Nguyen

  DOI：10.1021/jo702436p

  日期：2008.2.1

  [GRAPHICS]The development of a new method for stereoselective glycosylation with glycosyl trichloroacetimidate donors employing cationic palladium(II), Pd(CH3CN)(4)(BF4)(2), is described. This process employs Pd(CH3CN)(4)(BF4)(2) as an efficient activator, providing access to a variety of disaccharides and glycopeptides. This reaction is highly stereoselective and proceeds under mild conditions with low catalyst loading. Interestingly, this palladium catalysis directs beta-glucosylations in the absence of classical neighboring group participation.
• Sulfoxide Covalent Catalysis: Application to Glycosidic Bond Formation
  作者：Timothy A. Boebel、David Y. Gin

  DOI：10.1002/anie.200352761

  日期：2003.12.8
• Retention of the anomeric configuration in the imidate procedure: synthesis of disaccharides containing α-l-rhamnopyranosyl and α-d-mannopyranosyl groups
  作者：Péter Fügedi、András Lipták、Pál Nánási、András Neszmélyi

  DOI：10.1016/s0008-6215(00)80788-0

  日期：1982.9