p-tolyl 2,3,4-tri-O-benzoyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside | 1178514-89-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-tolyl 2,3,4-tri-O-benzoyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside
• 英文别名: p-tolyl 6-O-chloroacetyl-1-thio-2,3,4-tri-O-benzoyl-α-D-mannopyranoside；[(2R,3R,4S,5S,6R)-4,5-dibenzoyloxy-2-[(2-chloroacetyl)oxymethyl]-6-(4-methylphenyl)sulfanyloxan-3-yl] benzoate
• CAS: 1178514-89-0
• 化学式: C₃₆H₃₁ClO₉S
• 分子量: 675.156
• InChiKey: YRTAZWQAJDEFFT-RVSNDKTFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8
• 重原子数：
  47
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  p-tolyl 2,3,4-tri-O-benzoyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside 、 p-methoxyphenyl 4-O-benzoyl-2-O-benzyl-α-L-fucopyranosyl-(1→3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以82%的产率得到p-methoxyphenyl 2,3,4-tri-O-benzoyl-6-O-chloroacetyl-α-D-mannopyranosyl-(1→3)-4-O-benzoyl-2-O-benzyl-α-L-fucopyranosyl-(1→3)-4,6-O-benzylidene-2-deoxy-2-phthalimido-β-D-glucopyranoside
  参考文献：
  名称：

  Concise synthesis of the tetrasaccharide repeating unit of the O-polysaccharide isolated from Edwardsiella tarda PCM 1156 strain

  摘要：

  A convergent strategy has been developed for the synthesis of the tetrasaccharide repeating unit of the O-antigen from Edwardsiella tarda PCM 1156. Sequential glycosylations of a series of rationally protected monosaccharide intermediates were achieved either by the activation of thioglycosides using N-iodosuccinimide (NIS) in conjunction with H2SO4-silica or by activation of trichloroacetimidate by H2SO4-silica only. All glycosylation reactions resulted in the formation of the desired linkage with absolute stereoselectivity and yielded the required derivatives in good to excellent yields. Both azido and phthalimido groups have been used as the precursor of the desired acetamido group depending on the requirement of 1,2-cis- or 1,2-trans-glycosidic linkage. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.08.004
• 作为产物：
  描述：

  p-tolyl 2,3,4-tri-O-benzoyl-1-thio-α-D-mannopyranoside 、 氯乙酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到p-tolyl 2,3,4-tri-O-benzoyl-6-O-chloroacetyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Concise synthesis of the tetrasaccharide repeating unit of the O-polysaccharide isolated from Edwardsiella tarda PCM 1156 strain

  摘要：

  A convergent strategy has been developed for the synthesis of the tetrasaccharide repeating unit of the O-antigen from Edwardsiella tarda PCM 1156. Sequential glycosylations of a series of rationally protected monosaccharide intermediates were achieved either by the activation of thioglycosides using N-iodosuccinimide (NIS) in conjunction with H2SO4-silica or by activation of trichloroacetimidate by H2SO4-silica only. All glycosylation reactions resulted in the formation of the desired linkage with absolute stereoselectivity and yielded the required derivatives in good to excellent yields. Both azido and phthalimido groups have been used as the precursor of the desired acetamido group depending on the requirement of 1,2-cis- or 1,2-trans-glycosidic linkage. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.08.004

文献信息

• Imidazolium Cation Supported Solution-Phase Assembly of Homolinear α(1→6)−Linked Octamannoside: An Efficient Alternate Approach for Oligosaccharide Synthesis
  作者：Charu K. Yerneni、Vibha Pathak、Ashish K. Pathak

  DOI：10.1021/jo901169u

  日期：2009.8.21

  An efficient, simple convergent assembly of a homolinear alpha(1 -> 6)-linked octamannosyl thioglycoside was obtained starting from imidazolium cation-tagged mannosyl fluoride and thiomannoside using block couplings. During chain elongation glycosylation reactions no column chromatographic purifications were used.
• Concise synthesis of the tetrasaccharide repeating unit of the O-polysaccharide isolated from Edwardsiella tarda PCM 1156 strain
  作者：Rituparna Das、Mukul Mahanti、Balaram Mukhopadhyay

  DOI：10.1016/j.carres.2014.08.004

  日期：2014.11

  A convergent strategy has been developed for the synthesis of the tetrasaccharide repeating unit of the O-antigen from Edwardsiella tarda PCM 1156. Sequential glycosylations of a series of rationally protected monosaccharide intermediates were achieved either by the activation of thioglycosides using N-iodosuccinimide (NIS) in conjunction with H2SO4-silica or by activation of trichloroacetimidate by H2SO4-silica only. All glycosylation reactions resulted in the formation of the desired linkage with absolute stereoselectivity and yielded the required derivatives in good to excellent yields. Both azido and phthalimido groups have been used as the precursor of the desired acetamido group depending on the requirement of 1,2-cis- or 1,2-trans-glycosidic linkage. (C) 2014 Elsevier Ltd. All rights reserved.