(6S,8R,9R,10R,11R)-9,10-Diacetoxy-8-acetoxymethyl-11-azido-3-tert-butoxycarbonylamino-1,7-dioxa-spiro[5.5]undec-4-ene-3-carboxylic acid methyl ester | 364631-79-8

• 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: (6S,8R,9R,10R,11R)-9,10-Diacetoxy-8-acetoxymethyl-11-azido-3-tert-butoxycarbonylamino-1,7-dioxa-spiro[5.5]undec-4-ene-3-carboxylic acid methyl ester
• CAS: 364631-79-8
• 化学式: C₂₃H₃₂N₄O₁₂
• 分子量: 556.527
• InChiKey: FKUYFWUHDAJLKO-GGJAZIJJSA-N

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 (6S,8R,9R,10R,11R)-9,10-Diacetoxy-8-acetoxymethyl-11-azido-3-tert-butoxycarbonylamino-1,7-dioxa-spiro[5.5]undec-4-ene-3-carboxylic acid methyl ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以0.101 mmol的产率得到(3R,6S,8R,9R,10R,11R)-9,10-Diacetoxy-8-acetoxymethyl-11-acetylamino-3-tert-butoxycarbonylamino-1,7-dioxa-spiro[5.5]undecane-3-carboxylic acid methyl ester
  参考文献：
  名称：

  New design concepts for constraining glycosylated amino acids

  摘要：

  In an effort to probe the mechanism by which glycosyltransferases recognize glycoproteins and assemble the core structures of O-linked oligosaccharides, two constrained glycopeptides based on the alpha -N-acetylgalactosaminyl serine substructure were chosen for synthesis. These compounds representing one of the two possible gauche conformations of the D-serine and L-serine configurations of the parent substructure were successfully prepared in reasonable overall yield through a convergent strategy. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00545-2
• 作为产物：
  描述：

  [(6S,8R,9S,10R,11R)-11-Azido-9,10-bis-(tert-butyl-dimethyl-silanyloxy)-8-(tert-butyl-diphenyl-silanyloxymethyl)-3-hydroxymethyl-1,7-dioxa-spiro[5.5]undec-4-en-3-yl]-carbamic acid tert-butyl ester 在 吡啶 、 四丁基氟化铵 、 碳酸氢钠 、 戴斯-马丁氧化剂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 苯 为溶剂， 反应 45.5h， 生成 (6S,8R,9R,10R,11R)-9,10-Diacetoxy-8-acetoxymethyl-11-azido-3-tert-butoxycarbonylamino-1,7-dioxa-spiro[5.5]undec-4-ene-3-carboxylic acid methyl ester
  参考文献：
  名称：

  New design concepts for constraining glycosylated amino acids

  摘要：

  In an effort to probe the mechanism by which glycosyltransferases recognize glycoproteins and assemble the core structures of O-linked oligosaccharides, two constrained glycopeptides based on the alpha -N-acetylgalactosaminyl serine substructure were chosen for synthesis. These compounds representing one of the two possible gauche conformations of the D-serine and L-serine configurations of the parent substructure were successfully prepared in reasonable overall yield through a convergent strategy. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(01)00545-2