methyl (2S)-4-[(2S,3R,4S,5R,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]sulfanyl-2-(phenylmethoxycarbonylamino)butanoate | 1263182-18-8

• 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: methyl (2S)-4-[(2S,3R,4S,5R,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]sulfanyl-2-(phenylmethoxycarbonylamino)butanoate
• CAS: 1263182-18-8
• 化学式: C₃₉H₅₁NO₂₁S
• 分子量: 901.894
• InChiKey: DRMVLQUZMSYMCP-XFHYEMFTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  62
• 可旋转键数：
  28
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  302
• 氢给体数：
  1
• 氢受体数：
  22

反应信息

• 作为产物：
  描述：

  (S)-2-(苄氧羰氨基)-3-丁烯酸甲酯 、 2,3,6-tri-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranose 在 安息香双甲醚 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 以89%的产率得到methyl (2S)-4-[(2S,3R,4S,5R,6R)-3,4-diacetyloxy-6-(acetyloxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]sulfanyl-2-(phenylmethoxycarbonylamino)butanoate
  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