(1S,2R)-1-((2R,3R,4S)-4-acetoxy-3-(N-(tert-butoxycarbonyl)acetamido)-6-(dodecylthio)-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate | 957218-48-3

• 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: (1S,2R)-1-((2R,3R,4S)-4-acetoxy-3-(N-(tert-butoxycarbonyl)acetamido)-6-(dodecylthio)-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate
• CAS: 957218-48-3
• 化学式: C₃₇H₆₁NO₁₄S
• 分子量: 775.956
• InChiKey: WFOFMYIQELIECE-BYXGWVTCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.81
• 重原子数：
  53.0
• 可旋转键数：
  21.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  187.34
• 氢给体数：
  0.0
• 氢受体数：
  15.0

反应信息

• 作为反应物：
  描述：

  (1S,2R)-1-((2R,3R,4S)-4-acetoxy-3-(N-(tert-butoxycarbonyl)acetamido)-6-(dodecylthio)-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 、 双丙酮半乳糖 在 N-碘代丁二酰亚胺 、 三氟甲磺酸 作用下， 反应 16.0h， 以100%的产率得到methyl (2R,4S,5R,6R)-5-[acetyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]-4-acetyloxy-2-[[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]methoxy]-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
  参考文献：
  名称：

  Synthesis of N,N-Ac,Boc laurylthio sialoside and its application to O-sialylation

  摘要：

  The combination of the 5-N-tert-butoxycarbonyl (Boc) group of laurylthio sialoside and cyclopentyl methyl ether (CPME) as a solvent enhanced the reactivity and alpha-selectivity of the sialyl donor during sialylation. Selective deprotection of the N-Boc group of sialoside, including an acid-sensitive isopropylidene function, was successfully achieved by Yb(OTf)(3)-SiO2. Transformation of NN-Ac,Boc into an N-acetylglycolyl group of sialoglycoside was easily performed via selective N-deacylation of the mixed Ac-N-Boc carbamate, subsequent Boc group removal, and acylation. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.08.088
• 作为产物：
  描述：

  二碳酸二叔丁酯 、 (4S,5R,6R)-4-Acetoxy-5-acetylamino-2-dodecylsulfanyl-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester 在 4-二甲氨基吡啶 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以99%的产率得到(1S,2R)-1-((2R,3R,4S)-4-acetoxy-3-(N-(tert-butoxycarbonyl)acetamido)-6-(dodecylthio)-6-(methoxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate
  参考文献：
  名称：

  Synthesis of N,N-Ac,Boc laurylthio sialoside and its application to O-sialylation

  摘要：

  The combination of the 5-N-tert-butoxycarbonyl (Boc) group of laurylthio sialoside and cyclopentyl methyl ether (CPME) as a solvent enhanced the reactivity and alpha-selectivity of the sialyl donor during sialylation. Selective deprotection of the N-Boc group of sialoside, including an acid-sensitive isopropylidene function, was successfully achieved by Yb(OTf)(3)-SiO2. Transformation of NN-Ac,Boc into an N-acetylglycolyl group of sialoglycoside was easily performed via selective N-deacylation of the mixed Ac-N-Boc carbamate, subsequent Boc group removal, and acylation. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.08.088