6-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose | 153947-47-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• 英文别名: O-(2-Acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-(1->6)-1,2,3,4-di-O-isopropylidene-α-D-galactopyranose；[(2R,3S,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-3-yl] acetate
• CAS: 153947-47-8
• 化学式: C₄₁H₅₀O₁₂
• 分子量: 734.841
• InChiKey: DWMUSAVSFFDDLY-GCXNFPDASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  53
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  119
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  6-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以67%的产率得到3,4,6-tri-O-benzyl-β-D-mannopyranosyl-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  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：

  (2R,4S,5R,6R)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)-2-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]oxan-3-one 在 吡啶 、 sodium tetrahydroborate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 18.0h， 生成 6-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  Route from Glycals to Mannose .beta.-Glycosides

  摘要：

  DOI：

  10.1021/jo00086a047

文献信息

• A practical synthesis of β-d-mannopyranosides
  作者：Alois Fürstner、Ingo Konetzki

  DOI：10.1016/s0040-4039(98)01163-0

  日期：1998.8

  An indirect yet highly efficient protocol for the β-d-mannosylation of sterically hindered alcohols is reported. Trichloroacetimidate 5 is used a key building block which is converted into the desired mannosides 9 via triflates 8 by an ultrasound promoted β-d-gluco → β-d-manno inversion process.

  据报道，用于空间受阻醇的β- d-甘露糖基化的间接但高效的方案。三氯乙酰亚胺酯5被使用的密钥构建块被转换成期望的甘露糖苷9通过三氟甲磺酸酯8通过超声波促进β- d -葡糖→β- d -甘露反转处理。
• Protecting Group and Solvent Effects in Electrochemical Glycosylation
  作者：Antony Fairbanks、Ludovic Drouin、Richard Compton、Nicole Fietkau

  DOI：10.1055/s-2007-986644

  日期：——

  An investigation is undertaken into the roles of pro-tecting groups and the solvent in the electrochemical-mediated -glycosylation of MANNO thioglycosides. Herein notable differences are observed between electrochemical and chemical glycosylation.

  对保护基团和溶剂在甘露诺硫糖苷的电化学介导的糖基化中的作用进行了研究。在此观察到电化学和化学糖基化之间的显着差异。
• Stereospecific Access to β-Mannosides from Glucose-derived 1,2-Orthoesters as Glycosyl Donors
  作者：Eisuke Kaji、Yugo Hosokawa、Yusuke Watanabe、Mina Kobayashi、Mayumi Yamakawa

  DOI：10.3987/com-03-s60

  日期：——

  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.