tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside | 1017587-62-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
• 英文别名: [(2S,3R,4R,5S,6R)-3-azido-4-phenylmethoxy-6-(phenylmethoxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-tris(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-tert-butyl-diphenylsilane
• CAS: 1017587-62-0
• 化学式: C₇₀H₇₅N₃O₁₀Si
• 分子量: 1146.47
• InChiKey: VFMCDDGDXDREEF-VRGBMCOBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.85
• 重原子数：
  84
• 可旋转键数：
  28
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为产物：
  描述：

  苯基2,3,4,6-四-O-苯甲基-1-硫代-Β-D-半乳糖皮蒽 、 t-butyldiphenylsilyl 2-azido-3,6-di-O-benzyl-2-deoxy-β-D-dlucopyranoside 在 4 A molecular sieve 、 sulfobromophthalein sodium 、 三氟甲磺酸酐 作用下， 以 various solvent(s) 为溶剂， 反应 0.67h， 以74%的产率得到tert-butyldiphenylsilyl 2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Stereoselective synthesis of benzyl-protected β-galactosides by propionitrile-mediated glycosylation

  摘要：

  beta-Selective galactosylation was studied using a series of 2-O-benzylated phenyl 1-thio-galactosides and glycosyl acceptors in propionitrile with BSP-TTBP-Tf2O. The glycosylation enabled us to synthesize useful precursors of N-acetyllactosamine and core 1 O-glycoserine derivatives in a highly convergent manner. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.01.029

文献信息

• Stereoselective synthesis of benzyl-protected β-galactosides by propionitrile-mediated glycosylation
  作者：Akiharu Ueki、Masafumi Hirota、Yuta Kobayashi、Keiko Komatsu、Yutaka Takano、Michio Iwaoka、Yuko Nakahara、Hironobu Hojo、Yoshiaki Nakahara

  DOI：10.1016/j.tet.2008.01.029

  日期：2008.3

  beta-Selective galactosylation was studied using a series of 2-O-benzylated phenyl 1-thio-galactosides and glycosyl acceptors in propionitrile with BSP-TTBP-Tf2O. The glycosylation enabled us to synthesize useful precursors of N-acetyllactosamine and core 1 O-glycoserine derivatives in a highly convergent manner. (c) 2008 Elsevier Ltd. All rights reserved.