tert-butyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylpentanoate | 1263182-13-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylpentanoate
• CAS: 1263182-13-3
• 化学式: C₃₈H₄₇NO₁₃S
• 分子量: 757.856
• InChiKey: RHBSLCYSCYIMND-KBEGACGUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  53
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  204
• 氢给体数：
  1
• 氢受体数：
  14

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylpentanoate 在 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 21.0h， 生成 ethyl (2S)-2-[[(2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylpentanoyl]amino]-3-phenylpropanoate
  参考文献：
  名称：

  Synthesis of S-glycosyl amino acids and S-glycopeptides via photoinduced click thiol–ene coupling

  摘要：

  We report on the photoinduced addition of glycosyl thiols to alkenyl glycines (thiol-ene coupling) to give S-glycosyl amino acids in high yields (53-90%). One of the amino acids thus prepared was used in the construction of a tripeptide via solution phase chemistry. Moreover, a one-pot two-step approach to an S-glycopeptide was developed using glutathione (GSH) as model starting material. This approach involved GSH S-alkenylation followed by photoinduced hydrothiolation by a glycosyl thiol. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2010.11.097
• 作为产物：
  描述：

  1,2,3,4,6-alpha-D-葡萄糖五乙酸酯 在 三乙基硅烷 、 碘 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 4.33h， 生成 tert-butyl (2S)-2-(9H-fluoren-9-ylmethoxycarbonylamino)-5-[(2S,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]sulfanylpentanoate
  参考文献：
  名称：

  Straightforward Entry to S-Glycosylated Fmoc-Amino Acids and Their Application to Solid Phase Synthesis of Glycopeptides and Glycopeptidomimetics

  摘要：

  Streamlined access to S-glycosylated Fmoc-amino acids was developed. The process provides diverse glycosylated modified amino acids in high yield and stereoselectivity taking advantage of the in situ generation of a glycosylthiolate obtained from carbohydrate acetates in a few steps. Mild basic conditions make the conjugation reaction compatible with Fmoc-iodo-amino acids. To validate the strategy the glycosylated building blocks were used for SPPS and the unprecedented incorporation of a long thio-oligosaccharide to the peptide chain was demonstrated.

  DOI：

  10.1021/ol503664t