Phenyl-carbamic acid (2R,3R,4S,5R,6R)-2,3,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester | 115533-28-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: Phenyl-carbamic acid (2R,3R,4S,5R,6R)-2,3,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester
• 英文别名: 3-O-(N-phenylcarbamoyl)-D-glucopyranose
• CAS: 115533-28-3
• 化学式: C₁₃H₁₇NO₇
• 分子量: 299.28
• InChiKey: NTMYXLCWFQITLF-JPIWQCGSSA-N

物化性质

• 沸点：
  510.5±50.0 °C(predicted)
• 密度：
  1.52±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.97
• 重原子数：
  21.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  128.48
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  Phenyl-carbamic acid (2R,3R,4S,5R,6R)-2,3,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester 在 吡啶 、 4-二甲氨基吡啶 、 三氟甲磺酸三甲基硅酯 作用下， 以 二氯甲烷 为溶剂， 反应 149.0h， 生成 (-)-menthyl 2,4,6-tri-O-acetyl-3-O-(N-phenylcarbamoyl)-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of β-d-mannosides from β-d-glucosides via an intramolecular Sn2 reaction at C-2

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(00)90561-5
• 作为产物：
  描述：

  1,2-O-isopropylidene-3-O-phenylcarbamoyl-α-D-glucofuranose 在 硫酸 作用下， 以 1,4-二氧六环 为溶剂， 反应 5.0h， 以87%的产率得到Phenyl-carbamic acid (2R,3R,4S,5R,6R)-2,3,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-4-yl ester
  参考文献：
  名称：

  Synthesis of β-d-mannosides from β-d-glucosides via an intramolecular Sn2 reaction at C-2

  摘要：

  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.

  DOI：

  10.1016/s0008-6215(00)90561-5

文献信息

• Synthesis of a core-fucosylated, biantennary octasaccharide as a precursor for glycopeptides of complex N-glycans
  作者：Joachim Seifert、Carlo Unverzagt

  DOI：10.1016/0040-4039(96)01394-9

  日期：1996.9

  A convergent synthesis of the biantennary and core-fucosylated octasaccharide 20 (a protected form of A) is described. Octasaccharide 20 is designed to serve as a precursor for dodecasaccharide 1, a complex N-glycan frequently found in glycoproteins of the serum and the cell surface.

  描述了双触角和岩藻糖基化的八糖20（A的保护形式）的会聚合成。八糖20被设计用作十二糖1的前体，十二糖1是在血清和细胞表面的糖蛋白中经常发现的一种复杂的N-聚糖。
• 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。