N-(9-Fluorenylmethoxycarbonyl)-O-(2-azido-4,6-benzylidene-3-O-chloroacetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester | 282736-09-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N-(9-Fluorenylmethoxycarbonyl)-O-(2-azido-4,6-benzylidene-3-O-chloroacetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester
• 英文别名: N-(9-fluorenylmethoxycarbonyl)-O-(2-azido-4,6-O-benzylidene-3-O-(2-chloroacetyl)-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester；benzyl (2S,3R)-3-[[(2S,4aR,6S,7R,8R,8aR)-7-azido-8-(2-chloroacetyl)oxy-2-phenyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-2-(9H-fluoren-9-ylmethoxycarbonylamino)butanoate
• CAS: 282736-09-8
• 化学式: C₄₁H₃₉ClN₄O₁₀
• 分子量: 783.234
• InChiKey: MOXNYGSEYKAZAB-IOEDDWEISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.3
• 重原子数：
  56
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  142
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  N-(9-Fluorenylmethoxycarbonyl)-O-(2-azido-4,6-benzylidene-3-O-chloroacetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester 在 palladium on activated charcoal N-碘代丁二酰亚胺 、 三氟甲磺酸 、 氢气 、 硫脲 作用下， 以 甲醇 、 二氯甲烷 、 乙腈 为溶剂， 生成 N^α-fluoren-9-ylmethoxycarbonyl-3-O-[2-acetamido-4,6-O-benzylidene-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-galactopyranosyl]-L-threonine
  参考文献：
  名称：

  A concise synthesis of the O-glycosylated amino acid building block; using phenyl selenoglycoside as a glycosyl donor

  摘要：

  A new glycosylation methodology for synthesizing a protected TF antigen is described. The key step is to use phenyl selenoglycoside as a glycosyl donor, thereby successfully establishing O-linked Fmoc-protected threoninyl monosaccharide in an excellent yield with high alpha selectivity. From protected D-galactal, a protected TF antigen building block is obtained in 40% total yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00367-1
• 作为产物：
  描述：

  苯基硒基-2-叠氮基-3,4,6-三-O-乙酰基-α-D-吡喃半乳糖苷 在 calcium sulfate ammonium hydroxide 、 silver trifluoromethanesulfonate 、 碳酸氢钠 、 potassium carbonate 、 对甲苯磺酸 、 1,1,3,3-四甲基脲 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 43.0h， 生成 N-(9-Fluorenylmethoxycarbonyl)-O-(2-azido-4,6-benzylidene-3-O-chloroacetyl-2-deoxy-α-D-galactopyranosyl)-L-threonine benzyl ester
  参考文献：
  名称：

  Facile Solid-Phase Synthesis of an Antifreeze Glycoprotein

  摘要：

  DOI：

  10.1002/1521-3765(20010202)7:3<585::aid-chem585>3.3.co;2-y

文献信息

• A stereocontrolled construction of 2-azido-2-deoxy-1,2-cis-α-galactosidic linkages utilizing 2-azido-4,6-O-benzylidene-2-deoxygalactopyranosyl diphenyl phosphates: stereoselective synthesis of mucin core 5 and core 7 structures
  作者：Kosuke Kakita、Toshifumi Tsuda、Noritoshi Suzuki、Seiichi Nakamura、Hisanori Nambu、Shunichi Hashimoto

  DOI：10.1016/j.tet.2012.04.059

  日期：2012.6

  TMSOTf-promoted glycosidation of 2-azido-4,6-O-benzylidene-2-deoxygalactosyl diphenyl phosphates with fluorenylmethoxycarbonyl (Fmoc)-protected serine and threonine derivatives in THF/Et2O (1:1) gave glycosyl amino acids in high yields and with excellent levels of alpha-selectivity (alpha/beta=94:6-95:5). The synthetic utility of the present glycosidation method was demonstrated by a stereoselective synthesis of mucin-type glycopeptide core 5 and core 7 building blocks, which are suitable for Fmoc-based solid-phase synthesis of O-glycopeptides. (C) 2012 Elsevier Ltd. All rights reserved.
• A concise synthesis of the O-glycosylated amino acid building block; using phenyl selenoglycoside as a glycosyl donor
  作者：Weir-Torn Jiaang、Meng-Yang Chang、Ping-Hui Tseng、Shui-Tein Chen

  DOI：10.1016/s0040-4039(00)00367-1

  日期：2000.4

  A new glycosylation methodology for synthesizing a protected TF antigen is described. The key step is to use phenyl selenoglycoside as a glycosyl donor, thereby successfully establishing O-linked Fmoc-protected threoninyl monosaccharide in an excellent yield with high alpha selectivity. From protected D-galactal, a protected TF antigen building block is obtained in 40% total yield. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Facile Solid-Phase Synthesis of an Antifreeze Glycoprotein
  作者：Ping-Hui Tseng、Weir-Torn Jiaang、Meng-Yang Chang、Shui-Tein Chen

  DOI：10.1002/1521-3765(20010202)7:3<585::aid-chem585>3.3.co;2-y

  日期：2001.2.2