p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside | 1262589-19-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside
• 英文别名: p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1->3)-4-O-acetyl-2,6-di-O-benzyl-β-D-glucopyranoside
• CAS: 1262589-19-4
• 化学式: C₅₆H₅₄O₁₅
• 分子量: 967.036
• InChiKey: RBYUOASJKMFDOO-JHRYBFERSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.21
• 重原子数：
  71.0
• 可旋转键数：
  18.0
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  161.97
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside 在 三乙基硅烷 、 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.25h， 以81%的产率得到p-methoxyphenyl 2,3-di-O-benzoyl-6-O-benzyl-β-D-glucopyranosyl-(1 → 3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Chemical synthesis of a tetrasaccharide related to the exocellular polysaccharide from Rhodococcus sp. RHA1

  摘要：

  Chemical synthesis of the tetrasaccharide related to the exocellular polysaccharide from Rhodococcus sp. RHA1 is reported. The stereoselective glycosylations were achieved by activation of the thioglycoside donors using N-iodosuccinimide in the presence of La(OTf)(3) varying temperature per the need of 1,2-cis or 1,2-trans glycosylations. The target tetrasaccharide is reported in the form of its p-methoxyphenyl glycoside that can be cleaved selectively from the per-O-acetylated derivative allowing further glycoconjugate formation using trichloroacetimidate chemistry. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.05.018
• 作为产物：
  描述：

  4-甲氧苯基2,6-二-O-苄基-3,4-O-异亚丙基-β-D-吡喃半乳糖苷 在 N-碘代丁二酰亚胺 、 camphor-10-sulfonic acid 、 溶剂黄146 作用下， 以 二氯甲烷 、 水 、 乙腈 为溶剂， 反应 3.5h， 生成 p-methoxyphenyl 2,3-di-O-benzoyl-4,6-O-benzylidene-β-D-glucopyranosyl-(1→3)-4-O-acetyl-2,6-di-O-benzyl-β-D-galactopyranoside
  参考文献：
  名称：

  Chemical synthesis of a tetrasaccharide related to the exocellular polysaccharide from Rhodococcus sp. RHA1

  摘要：

  Chemical synthesis of the tetrasaccharide related to the exocellular polysaccharide from Rhodococcus sp. RHA1 is reported. The stereoselective glycosylations were achieved by activation of the thioglycoside donors using N-iodosuccinimide in the presence of La(OTf)(3) varying temperature per the need of 1,2-cis or 1,2-trans glycosylations. The target tetrasaccharide is reported in the form of its p-methoxyphenyl glycoside that can be cleaved selectively from the per-O-acetylated derivative allowing further glycoconjugate formation using trichloroacetimidate chemistry. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.05.018

文献信息

• La(OTf)3: An Efficient Promoter for Thioglycoside Activation in Conjunction with N-Iodosuccinimide
  作者：Balaram Mukhopadhyay、Somnath Mukherjee

  DOI：10.1055/s-0030-1259016

  日期：2010.12

  Use of La(OTf)3 as a Lewis acid promoter for N-iodosuccinimide-mediated activation of thioglycosides is reported. The glycosylation reactions proceeded smoothly with good to excellent yields and stereoselectivity.

  使用La(OTf)3作为路易斯酸促使剂，报告了N-碘代琥珀酰亚胺介导的硫糖苷活化。糖苷化反应顺利进行，产率良好至优异，立体选择性也很好。