S-(2-methoxy-9H-xanthen-9-yl)cysteine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: S-(2-methoxy-9H-xanthen-9-yl)cysteine
• 英文别名: (2R)-2-amino-3-[(2-methoxy-9H-xanthen-9-yl)sulfanyl]propanoic acid
• 化学式: C₁₇H₁₇NO₄S
• 分子量: 331.392
• InChiKey: YKMTUOCCNDWDRJ-KNVGNIICSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  107
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-芴甲基-N-琥珀酰亚胺基碳酸酯 、 S-(2-methoxy-9H-xanthen-9-yl)cysteine 在 三乙胺 作用下， 以 水 、 乙腈 为溶剂， 反应 3.0h， 以83%的产率得到N^α-(9-fluorenylmethyloxycarbonyl)-S-(2-methoxy-9H-xanthen-9-yl)cysteine
  参考文献：
  名称：

  Novel S-Xanthenyl Protecting Groups for Cysteine and Their Applications for the N^α-9-Fluorenylmethyloxycarbonyl (Fmoc) Strategy of Peptide Synthesis^1-3

  摘要：

  The 9H-xanthen-9-yl (Xan) and 2-methoxy-9H-xanthen-9-yl (2-Moxan) groups can be introduced onto sulfhydryl functions by S-alkylation reactions involving the corresponding xanthydrols, plus trifluoroacetic acid (TFA) as catalyst. Conversely, these groups are removed rapidly by acid in the presence of appropriate silane or thiol scavengers. The 3-methoxy-9H-xanthen-9-yl (3-Moxan) derivative was also studied, but abandoned for several reasons including challenging synthesis, excessive lability to acid, and insufficient stability in the presence of base. The N-alpha-9-fluorenyl-methyloxycarbonyl (Fmoc), S-Xan or 2-Moxan-protected cysteine derivatives were prepared and applied to the solid-phase syntheses of several model peptides. Selective removal of S-Xan and S-2-Moxan groups, while retaining tris(alkoxybenzyl)amide (PAL) anchoring, is best accomplished with TFA-CH2Cl2-Et3SiH (1:98.5:0.5), 25 degrees C, 2 h. Alternatively, oxidative deprotection of S-Xan or S-2-Moxan with iodine (10-20 equiv) or thallium(III) tris(trifluoroacetate) [Tl(tfa)(3)] (1-3 equiv) to provide disulfides can be carried out on peptide substrates both in solution and while polymer-bound. Compared to established chemistries with the acid-labile and oxidizable S-triphenylmethyl (Trt) group, S-Xan and S-2-Moxan gave equal or superior results in terms of peptide purities (including no detectable tryptophan alkylation) and overall yields.

  DOI：

  10.1021/jo961882g
• 作为产物：
  描述：

  L-半胱氨酸 、 2-Methoxyxanthydrol 以 乙二醇二甲醚 、 三氟乙酸 为溶剂， 反应 0.5h， 以97%的产率得到S-(2-methoxy-9H-xanthen-9-yl)cysteine
  参考文献：
  名称：

  Novel S-Xanthenyl Protecting Groups for Cysteine and Their Applications for the N^α-9-Fluorenylmethyloxycarbonyl (Fmoc) Strategy of Peptide Synthesis^1-3

  摘要：

  The 9H-xanthen-9-yl (Xan) and 2-methoxy-9H-xanthen-9-yl (2-Moxan) groups can be introduced onto sulfhydryl functions by S-alkylation reactions involving the corresponding xanthydrols, plus trifluoroacetic acid (TFA) as catalyst. Conversely, these groups are removed rapidly by acid in the presence of appropriate silane or thiol scavengers. The 3-methoxy-9H-xanthen-9-yl (3-Moxan) derivative was also studied, but abandoned for several reasons including challenging synthesis, excessive lability to acid, and insufficient stability in the presence of base. The N-alpha-9-fluorenyl-methyloxycarbonyl (Fmoc), S-Xan or 2-Moxan-protected cysteine derivatives were prepared and applied to the solid-phase syntheses of several model peptides. Selective removal of S-Xan and S-2-Moxan groups, while retaining tris(alkoxybenzyl)amide (PAL) anchoring, is best accomplished with TFA-CH2Cl2-Et3SiH (1:98.5:0.5), 25 degrees C, 2 h. Alternatively, oxidative deprotection of S-Xan or S-2-Moxan with iodine (10-20 equiv) or thallium(III) tris(trifluoroacetate) [Tl(tfa)(3)] (1-3 equiv) to provide disulfides can be carried out on peptide substrates both in solution and while polymer-bound. Compared to established chemistries with the acid-labile and oxidizable S-triphenylmethyl (Trt) group, S-Xan and S-2-Moxan gave equal or superior results in terms of peptide purities (including no detectable tryptophan alkylation) and overall yields.

  DOI：

  10.1021/jo961882g

文献信息

• Novel <i>S</i>-Xanthenyl Protecting Groups for Cysteine and Their Applications for the <i>N</i>^α-9-Fluorenylmethyloxycarbonyl (Fmoc) Strategy of Peptide Synthesis^1-3
  作者：Yongxin Han、George Barany

  DOI：10.1021/jo961882g

  日期：1997.6.13

  The 9H-xanthen-9-yl (Xan) and 2-methoxy-9H-xanthen-9-yl (2-Moxan) groups can be introduced onto sulfhydryl functions by S-alkylation reactions involving the corresponding xanthydrols, plus trifluoroacetic acid (TFA) as catalyst. Conversely, these groups are removed rapidly by acid in the presence of appropriate silane or thiol scavengers. The 3-methoxy-9H-xanthen-9-yl (3-Moxan) derivative was also studied, but abandoned for several reasons including challenging synthesis, excessive lability to acid, and insufficient stability in the presence of base. The N-alpha-9-fluorenyl-methyloxycarbonyl (Fmoc), S-Xan or 2-Moxan-protected cysteine derivatives were prepared and applied to the solid-phase syntheses of several model peptides. Selective removal of S-Xan and S-2-Moxan groups, while retaining tris(alkoxybenzyl)amide (PAL) anchoring, is best accomplished with TFA-CH2Cl2-Et3SiH (1:98.5:0.5), 25 degrees C, 2 h. Alternatively, oxidative deprotection of S-Xan or S-2-Moxan with iodine (10-20 equiv) or thallium(III) tris(trifluoroacetate) [Tl(tfa)(3)] (1-3 equiv) to provide disulfides can be carried out on peptide substrates both in solution and while polymer-bound. Compared to established chemistries with the acid-labile and oxidizable S-triphenylmethyl (Trt) group, S-Xan and S-2-Moxan gave equal or superior results in terms of peptide purities (including no detectable tryptophan alkylation) and overall yields.