6-O-(3,4,6-tri-O-benzyl-2-O-trifluoromethanesulfonyl-β-D-glucopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose | 213028-97-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-(3,4,6-tri-O-benzyl-2-O-trifluoromethanesulfonyl-β-D-glucopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
• 英文别名: [(2R,3R,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] trifluoromethanesulfonate
• CAS: 213028-97-8
• 化学式: C₄₀H₄₇F₃O₁₃S
• 分子量: 824.867
• InChiKey: IMEWWKVVBNMUOD-CABRARQTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  57
• 可旋转键数：
  15
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  144
• 氢给体数：
  0
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  6-O-(3,4,6-tri-O-benzyl-2-O-trifluoromethanesulfonyl-β-D-glucopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 在 18-冠醚-6 、 sodium methylate 作用下， 以 甲醇 为溶剂， 生成 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：

  3,4,6-三-O-乙酰基-alpha-D-吡喃葡萄糖1,2-(乙基原乙酸酯) 在 吡啶 、 氢氧化钾 、 三氟化硼乙醚 、 potassium methanolate 、 caesium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 16.0h， 生成 6-O-(3,4,6-tri-O-benzyl-2-O-trifluoromethanesulfonyl-β-D-glucopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose
  参考文献：
  名称：

  实用合成β-d-甘露聚糖

  摘要：

  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。

  DOI：

  10.1016/s0040-4039(98)01163-0

文献信息

• 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.
• Expedient Stereospecific Synthesis of b-Mannosides from a Glucose-derived 1,2-Orthoester
  作者：Eisuke Kaji、Yugo Hosokawa

  DOI：10.3987/com-99-s100

  日期：——

  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.
• 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。