Bn(-3)[Bn(-4)][TBDPS(-6)]Glc(b)-O-Bz | 208656-45-5

• 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: Bn(-3)[Bn(-4)][TBDPS(-6)]Glc(b)-O-Bz
• 英文别名: [(2S,3R,4R,5R,6R)-6-[[tert-butyl(diphenyl)silyl]oxymethyl]-3-hydroxy-4,5-bis(phenylmethoxy)oxan-2-yl] benzoate
• CAS: 208656-45-5
• 化学式: C₄₃H₄₆O₇Si
• 分子量: 702.92
• InChiKey: BYTOHJPKENGASW-KHNNWAQNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.68
• 重原子数：
  51
• 可旋转键数：
  15
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  83.4
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  乙基beta-硫代吡喃葡萄糖苷四苄基 、 Bn(-3)[Bn(-4)][TBDPS(-6)]Glc(b)-O-Bz 在 iodonium di(2,4,6-collidinium) triflate 、 4 A molecular sieve 作用下， 以 乙醚 、 二氯甲烷 为溶剂， 反应 1.0h， 以72%的产率得到
  参考文献：
  名称：

  An Expeditious Route toStreptococciandEnterococciGlycolipidsViaRing-Opening of 1,2-Anhydrosugars with Protic Acids

  摘要：

  1,2-Anhydroglucose 6 reacts smoothly and with a high degree of stereoselectivity with a variety of carboxylic and phosphoric acids resulting in the formation of the predominantly beta-oriented 1-O-acyl and 1-O-phosphorylglucoses 7-17. This methodology has been successfully applied in the construction of glycolipids 1a,b. Ring-opening of the 1,2-anhydroglucose derivative 19 with benzoic acid furnished exclusively the beta-aligned key intermediate 20. Subsequent ICDT-assisted chemoselective alpha-glucosylation of 20 with thioethyl donor 21, followed by glycosidation of kojibiosyl benzoate 22 with glycerol acceptor 23 gave the fully protected alpha-diglucosyl glycerol derivative 25, which upon desilylation (-->28), acylation (-->29 or 30) and deprotection afforded the target glycolipids 1a-b in high overall yield.

  DOI：

  10.1080/07328309808002906
• 作为产物：
  描述：

  3,4-di-O-benzyl-6-O-tert-butyldiphenylsilyl-D-glucal 在 dimethoxydioxirane*H₂O 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 0.08h， 生成 Bn(-3)[Bn(-4)][TBDPS(-6)]Glc(b)-O-Bz
  参考文献：
  名称：

  An Expeditious Route toStreptococciandEnterococciGlycolipidsViaRing-Opening of 1,2-Anhydrosugars with Protic Acids

  摘要：

  1,2-Anhydroglucose 6 reacts smoothly and with a high degree of stereoselectivity with a variety of carboxylic and phosphoric acids resulting in the formation of the predominantly beta-oriented 1-O-acyl and 1-O-phosphorylglucoses 7-17. This methodology has been successfully applied in the construction of glycolipids 1a,b. Ring-opening of the 1,2-anhydroglucose derivative 19 with benzoic acid furnished exclusively the beta-aligned key intermediate 20. Subsequent ICDT-assisted chemoselective alpha-glucosylation of 20 with thioethyl donor 21, followed by glycosidation of kojibiosyl benzoate 22 with glycerol acceptor 23 gave the fully protected alpha-diglucosyl glycerol derivative 25, which upon desilylation (-->28), acylation (-->29 or 30) and deprotection afforded the target glycolipids 1a-b in high overall yield.

  DOI：

  10.1080/07328309808002906

文献信息

• An Expeditious Route to<i>Streptococci</i>and<i>Enterococci</i>Glycolipids<i>Via</i>Ring-Opening of 1,2-Anhydrosugars with Protic Acids
  作者：C. M. Timmers、N. C.R. van Straten、G. A. van der Marel、J. H. van Boom

  DOI：10.1080/07328309808002906

  日期：1998.4

  1,2-Anhydroglucose 6 reacts smoothly and with a high degree of stereoselectivity with a variety of carboxylic and phosphoric acids resulting in the formation of the predominantly beta-oriented 1-O-acyl and 1-O-phosphorylglucoses 7-17. This methodology has been successfully applied in the construction of glycolipids 1a,b. Ring-opening of the 1,2-anhydroglucose derivative 19 with benzoic acid furnished exclusively the beta-aligned key intermediate 20. Subsequent ICDT-assisted chemoselective alpha-glucosylation of 20 with thioethyl donor 21, followed by glycosidation of kojibiosyl benzoate 22 with glycerol acceptor 23 gave the fully protected alpha-diglucosyl glycerol derivative 25, which upon desilylation (-->28), acylation (-->29 or 30) and deprotection afforded the target glycolipids 1a-b in high overall yield.