1,3,4,6-tetra-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside | 82264-19-5

• 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: 1,3,4,6-tetra-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
• 英文别名: α-1,3,4,6-tetra-O-acetyl-2-N-benzyoxycarbonyl-D-glucosamine；(tetra-O-acetyl-α-D-glucopyranose-2-yl)-carbamic acid benzyl ester；(Tetra-O-acetyl-α-D-glucopyranose-2-yl)-carbamidsaeure-benzylester；[(2R,3S,4R,5R,6R)-3,4,6-triacetyloxy-5-(phenylmethoxycarbonylamino)oxan-2-yl]methyl acetate
• CAS: 82264-19-5
• 化学式: C₂₂H₂₇NO₁₁
• 分子量: 481.456
• InChiKey: WFUOWCBLXHATHL-ONUIULTDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  34
• 可旋转键数：
  13
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  153
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 生成 四-O-乙酰-2-氨基-D-葡萄糖
  参考文献：
  名称：

  Mild and simple biomimetic conversion of amines to carbonyl compounds

  摘要：

  DOI：

  10.1021/ja00380a019
• 作为产物：
  描述：

  N-benzyloxycarbonyl-D-glucosamine 在 吡啶 、 乙酸酐 作用下， 生成 2-(acetoxymethyl)-5-{[(benzyloxy)carbonyl]amino}tetrahydropyran-3,4,6-triyl triacetate 、 1,3,4,6-tetra-O-acetyl-2-benzyloxycarbonylamino-2-deoxy-α-D-glucopyranoside
  参考文献：
  名称：

  THE SYNTHESIS OF OXAZOLINE DERIVATIVES OF MONOSACCHARIDES AND THEIR RELATIONSHIP TO THE AMINO SUGARS¹

  摘要：

  DOI：

  10.1021/jo01180a002

文献信息

• Solid-Phase Synthesis of Di-N-Acetyl-β-Chitobiosyl NAG-Thiazoline
  作者：Gangliang Huang、Ya Chen

  DOI：10.2174/157018011796235220

  日期：2011.8.1

  The solid-phase synthesis of di-N-acetyl-β-chitobiosyl NAG (N-acetyl D-glucosamine)-thiazoline 3 was reported. After the 6-O-benzyl NAG-thiazoline 9, NHCbz trichloroacetimidate donors 14, and 21 were synthesized, and solid-phase synthesis was performed using the Wang resin as support. The target di-N-acetyl-β-chitobiosyl NAGthiazoline 3 was obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, and deacetylation, respectively.

  据报道，进行了双-N-乙酰-β-壳二糖基NAG（N-乙酰-D-葡萄糖胺）噻唑啉3的固相合成。首先合成了6-O-苄基NAG噻唑啉9、NHCbz三氯乙酸亚胺供体14和21，然后使用Wang树脂作为支持体进行固相合成。通过迭代糖基化反应、催化氢化、乙酰化和脱乙酰化，分别获得了目标双-N-乙酰-β-壳二糖基NAG噻唑啉3。
• Solid-Phase Synthesis of Di-N-Acetyl-β-Chitobiosyl Allosamizoline
  作者：Gangliang Huang

  DOI：10.2174/157017811799304331

  日期：2011.11.1

  The solid-phase synthesis of di-N-acetyl-β-chitobiosyl allosamizoline 2 was reported. After the 6-O-benzyl allosamizoline 16, NHCbz trichloroacetimidate donors 7, and 14 were synthesized; solid-phase synthesis was performed using the Wang resin as support. The target di-N-acetyl-β-chitobiosyl allosamizoline 2 was obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, and deacetylation, respectively.

  固相合成二-N-乙酰-β-壳二糖基别山黧豆碱2已见报道。在合成了6-O-苄基别山黧豆碱16、NHCbz三氯乙酰亚胺酯供体7和14之后，采用Wang树脂作为载体进行固相合成。目标二-N-乙酰-β-壳二糖基别山黧豆碱2通过反复糖基化反应、催化氢化、乙酰化和脱乙酰化分别获得。
• High-Efficiency Synthesis of Chitooligosaccharides
  作者：Gangliang Huang

  DOI：10.2174/157017811794557877

  日期：2011.1.1

  The solid-phase synthesis of chitooligosaccharides is described. After the NHCbz trichloroacetimidate donors 6 and 14 were synthesized; solid-phase synthesis was performed using the Wang resin as support. The illustrated tetra-Nacetyl- chitotetraose 1 was obtained by iterative glycosylation reactions, catalytic hydrogenation, acetylation, and deacetylation, respectively.

  固相合成壳寡糖的方法被描述如下：在合成NHCbz三氯乙亚胺酯供体6和14之后，使用Wang树脂作为载体进行固相合成。通过迭代的糖基化反应、催化氢化、乙酰化和脱乙酰化，分别得到了示例性的四乙酰化壳四糖1。
• Micheel et al., Chemische Berichte, 1955, vol. 88, p. 2011,2015
  作者：Micheel et al.

  DOI：——

  日期：——
• Mild and simple biomimetic conversion of amines to carbonyl compounds
  作者：Thomas F. Buckley、Henry Rapoport

  DOI：10.1021/ja00380a019

  日期：1982.8