tert-butyldiphenylsilyl 2,6-di-O-benzyl-3,4-di-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside | 1017587-69-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyldiphenylsilyl 2,6-di-O-benzyl-3,4-di-O-(4-methoxyphenyl)methyl-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-5-[(2S,3R,4S,5S,6R)-4,5-bis[(4-methoxyphenyl)methoxy]-3-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-4-phenylmethoxy-6-(phenylmethoxymethyl)oxan-2-yl]oxy-tert-butyl-diphenylsilane
• CAS: 1017587-69-7
• 化学式: C₇₂H₇₉N₃O₁₂Si
• 分子量: 1206.52
• InChiKey: JQHBJZLYMIKPAD-LFUISZFNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  12.87
• 重原子数：
  88
• 可旋转键数：
  30
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  125
• 氢给体数：
  0
• 氢受体数：
  14

反应信息

• 作为产物：
  描述：

  phenyl 2,6-di-O-benzyl-3,4-di-O-(4-methoxybenzyl)-1-thio-β-D-galactopyranoside 、 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， 生成 tert-butyldiphenylsilyl 2,6-di-O-benzyl-3,4-di-O-(4-methoxyphenyl)methyl-β-D-galactopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 、 tert-butyldiphenylsilyl 2,6-di-O-benzyl-3,4-di-O-(4-methoxyphenyl)methyl-α-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.