ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside | 35526-01-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-2-ethoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 35526-01-3
• 化学式: C₃₁H₃₆O₇
• 分子量: 520.623
• InChiKey: RACCVFONBPONCS-PXPWAULYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ethyl 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 ethyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside
  参考文献：
  名称：

  Expedient Stereospecific Synthesis of b-Mannosides from a Glucose-derived 1,2-Orthoester

  摘要：

  A new, stereospecific synthesis of beta-mannosides from glucose-derived 1,2-orthoester has been developed using a simple four-step procedure. For the synthesis of beta-D-Man-(1-->6)-D-Gal, a 6-OH free galactose derivative was glycosylated with the orthoester to yield beta-D-Glc-(1-->6)-D-Gal; the Glc unit of which was epimerized into the beta-mannoside in good yield.

  DOI：

  10.3987/com-99-s100
• 作为产物：
  描述：

  3,4,6-tri-O-benzyl-1,2-O-(exo-ethoxyethylidene)-α-D-glucopyranose 、 双丙酮半乳糖 在 高氯酸四乙基铵 、 (+)-10-camphorsulfonic acid 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 2.0h， 以54.6%的产率得到6-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
  参考文献：
  名称：

  Stereospecific Access to β-Mannosides from Glucose-derived 1,2-Orthoesters as Glycosyl Donors

  摘要：

  A new, stereospecific synthesis of beta-mannosides from glucose-derived 1,2-orthoesters has been developed by a simple four step procedure, comprising beta-specific glycosidation of the 1,2-orthoesters, 2'-O-deacetylation, 2'-O-triflation, and SN 2 type inversion of the triflyl group providing beta-D-Man-(1-->6)-D-Gal, and beta-D-Man-(1-->4)-D-Glc derivatives in reasonable yield.

  DOI：

  10.3987/com-03-s60