1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-mannopyranoside | 214334-28-8

• 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: 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S)-6-acetyloxy-3,4,5-tris(phenylmethoxy)oxan-2-yl]methyl acetate
• CAS: 214334-28-8
• 化学式: C₃₁H₃₄O₈
• 分子量: 534.606
• InChiKey: IFCAMEQHKHEHBS-IWBABOIGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  39
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  89.5
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-mannopyranoside 在 碘代三甲硅烷 、 magnesium oxide 作用下， 以 二氯甲烷 为溶剂， 反应 2.0h， 生成 Acetic acid (2R,3S,4S,5R,6R)-3,4,5-tris-benzyloxy-6-iodo-tetrahydro-pyran-2-ylmethyl ester
  参考文献：
  名称：

  Unique Reactions of Glycosyl Iodides with Oxa- and Thiocycloalkane Acceptors

  摘要：

  [GRAPHICS]Glc: R, R'''' = H; R', R'',R''' =OBn Gal: R', R''' =H; R', R'', R''' = OBn Man: R, R'''=H;R-1, R'''' =OBn; R''=OAcGlucosyl-, galactosyl-, and mannosyl iodides efficiently react with strained oxacycloalkane acceptors to afford O-glycosides with high-beta-selectivity. The mechanism of ring opening was investigated by reacting mannosyl iodides with pure enantiomers of propylene oxide and styrene oxide. Competition experiments between three- and five-membered oxacycloalkanes were also investigated. Finally, beta-thiomannosides were synthesized from thiocycloalkane acceptors.

  DOI：

  10.1021/ol049966w
• 作为产物：
  描述：

  (2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran 生成 1,6-di-O-acetyl-2,3,4-tri-O-benzyl-D-mannopyranoside
  参考文献：
  名称：

  SHAH, RAJAN N.;BAPTISTA, JOSE;PERDOMO, GUILLERMO R.;CARVER, JEREMY P.;KRE+, J. CARBOHYDR. CHEM., 6,(1987) N 4, 645-660

  摘要：

  DOI：

文献信息

• MURAKATA, CHIKARA;OGAWA, TOMOYA, TETRAHEDRON LETT., 31,(1990) N7, C. 2439-2442
  作者：MURAKATA, CHIKARA、OGAWA, TOMOYA

  DOI：——

  日期：——