Acetic acid (2R,3R,4S,5R,6R)-5,6-diacetoxy-2-acetoxymethyl-4-phenylcarbamoyloxy-tetrahydro-pyran-3-yl ester | 115533-29-4

• 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: Acetic acid (2R,3R,4S,5R,6R)-5,6-diacetoxy-2-acetoxymethyl-4-phenylcarbamoyloxy-tetrahydro-pyran-3-yl ester
• 英文别名: 1,2,4,6-tetra-O-acetyl-3-O-(N-phenylcarbamoyl)-β-D-glucopyranose
• CAS: 115533-29-4
• 化学式: C₂₁H₂₅NO₁₁
• 分子量: 467.43
• InChiKey: RKWMWADMHWRZTF-OUUBHVDSSA-N

物化性质

• 沸点：
  530.9±50.0 °C(predicted)
• 密度：
  1.34±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.32
• 重原子数：
  33.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  152.76
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-5,6-diacetoxy-2-acetoxymethyl-4-phenylcarbamoyloxy-tetrahydro-pyran-3-yl ester 在 氢溴酸 、 silver trifluoromethanesulfonate 作用下， 以 二氯甲烷 、 溶剂黄146 为溶剂， 生成 (-)-menthyl 2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Kunz, Horst; Guenther, Wolfgang, Angewandte Chemie, 1988, vol. 100, # 8, p. 1118 - 1119

  摘要：

  DOI：
• 作为产物：
  描述：

  1,2-5,6-di-O-isopropylidene-3-O-(N-phenylcarbamoyl)-α-D-glucofuranose 在 硫酸 作用下， 以 1,4-二氧六环 、 吡啶 、 水 为溶剂， 生成 Acetic acid (2R,3R,4S,5R,6R)-5,6-diacetoxy-2-acetoxymethyl-4-phenylcarbamoyloxy-tetrahydro-pyran-3-yl ester
  参考文献：
  名称：

  Kunz, Horst; Guenther, Wolfgang, Angewandte Chemie, 1988, vol. 100, # 8, p. 1118 - 1119

  摘要：

  DOI：

文献信息

• Synthesis of a Core Trisaccharide as a Versatile Building Block for N-Glycans and Glycoconjugates
  作者：Carlo Unverzagt

  DOI：10.1002/chem.200390156

  日期：2003.3.17

  N-linked oligosaccharides from glycoproteins (N-glycans) can be conveniently assembled with a building block approach. A protected form of the core trisaccharide (beta-mannosyl chitobiose) was identified as a key building block. The chitobiose part of the core trisaccharide was built from a glycosyl fluoride, which served as a precursor for the reducing GlcNAc azide and the inner GlcNAc moiety. Beta-mannosylation

  糖蛋白（N-聚糖）中的N-连接寡糖可通过构件方法方便地组装。核心三糖（β-甘露糖基壳二糖）的保护形式被确定为关键组成部分。核心三糖的壳二糖部分由糖基氟化物构建，该糖基氟化物用作还原性GlcNAc叠氮化物和内部GlcNAc部分的前体。β-甘露糖基化是在三糖阶段通过β-葡萄糖基壳二糖的分子内转化来完成的。β-甘露糖苷和叠氮基在核心三糖还原端的亚苄基保护可以模块化合成N-聚糖及其糖缀合物。
• Synthesis of β-d-mannosides from β-d-glucosides via an intramolecular Sn2 reaction at C-2
  作者：Wolfgang Günther、Horst Kunz

  DOI：10.1016/s0008-6215(00)90561-5

  日期：1992.4

  The selective synthesis of beta-D-mannosides was achieved by first synthesizing beta-D-glucosides that carry a N-phenylcarbamoyl protecting group at O-3. These derivatives were transformed into the corresponding beta-D-mannosides by intramolecular nucleophilic substitution with inversion of configuration at C-2, the O-triflyl group being the leaving group. Subsequent intramolecular attack of the neighboring carbamoyl group resulted in the formation of the 2,3-carbonate of the desired beta-D-mannoside.