2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside | 117253-41-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside
• 英文别名: 2-[(2R,3R,4S,5R,6R)-5-[[(3aS,4R,6S,7R,7aS)-2,2-dimethyl-7-phenylmethoxy-4-(phenylmethoxymethyl)-4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-6-yl]oxy]-3,4-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyethyl-trimethylsilane
• CAS: 117253-41-5
• 化学式: C₅₅H₆₈O₁₁Si
• 分子量: 933.224
• InChiKey: XLIIRUDXDGLOEJ-NJCNHQOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.89
• 重原子数：
  67
• 可旋转键数：
  23
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  102
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside 在 溶剂黄146 作用下， 反应 0.67h， 以75%的产率得到2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  2-(Trimethylsilyl)ethyl glycosides. 3. Synthesis, anomeric deblocking, and transformation into 1,2-trans 1-O-acyl sugars

  摘要：

  DOI：

  10.1021/jo00259a006
• 作为产物：
  描述：

  2-(trimethylsilyl)ethyl 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 在 sodium methylate 、 sodium hydride 、 对甲苯磺酸 、 溶剂黄146 作用下， 以 甲醇 为溶剂， 反应 7.17h， 生成 2-(trimethylsilyl)ethyl 2,3,6-tri-O-benzyl-4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-β-D-glucopyranoside
  参考文献：
  名称：

  2-(Trimethylsilyl)ethyl glycosides. 3. Synthesis, anomeric deblocking, and transformation into 1,2-trans 1-O-acyl sugars

  摘要：

  DOI：

  10.1021/jo00259a006

文献信息

• JANSSON, KARL;AHLFORS, STEFAN;FREJD, TORBJORN;KIHLBERG, JAN;MAGNUSSON, GO+, J. ORG. CHEM., 53,(1988) N 24, C. 5629-5647
  作者：JANSSON, KARL、AHLFORS, STEFAN、FREJD, TORBJORN、KIHLBERG, JAN、MAGNUSSON, GO+

  DOI：——

  日期：——
• 2-(Trimethylsilyl)ethyl glycosides. 3. Synthesis, anomeric deblocking, and transformation into 1,2-trans 1-O-acyl sugars
  作者：Karl Jansson、Stefan Ahlfors、Torbjoern Frejd、Jan Kihlberg、Goeran Magnusson、Jan Dahmen、Ghazi Noori、Kristina Stenvall

  DOI：10.1021/jo00259a006

  日期：1988.11
• A Practical Method for the Synthesis of Sialyl α-Glycosides
  作者：Valeri Martichonok、George M. Whitesides

  DOI：10.1021/ja960148b

  日期：1996.1.1

  Addition of 2,4-dimethylbenzenesulfenyl chloride to sialic acid glycal gives crystalline 2-chloro-3-thiosialic acid 3 in 85% yield. Reaction of 3 with sodium thiomethoxide in acetonitrile at 0 degrees C affords the sialic acid donor alpha-2-(methylthio)-3-thiosialic acid 4 in quantitative yield. Sialylation of glycosyl accepters 9 and 10 with 4 in the presence of phenylsulfenyl triflate (PST) as promotor in CH3CN at -40 degrees C gives alpha-sialosides in good yield and excellent stereoselectivity. No beta-sialosides are formed in either case. Removal of the auxiliary 3-(2,4-dimethylphenyl)-thio group is achieved in high yield using Ph(3)SnH and AIBN in refluxing toluene. Protected GM(3) trisaccharide and 6-sial-2-yllactose were obtained on a gram scale.