TBDMS 2-deoxy-2-(N-benzyloxycarbonylamino)-β-D-glucopyranoside | 1301718-54-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: TBDMS 2-deoxy-2-(N-benzyloxycarbonylamino)-β-D-glucopyranoside
• 英文别名: TBDMS 2-deoxy-N-benzyloxycarbonylamino-β-D-glucopyranoside
• CAS: 1301718-54-6
• 化学式: C₂₀H₃₃NO₇Si
• 分子量: 427.57
• InChiKey: YJWIXZVOGMRUQY-ZKXLYKBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.74
• 重原子数：
  29.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  117.48
• 氢给体数：
  4.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  苯甲醛二甲缩醛 、 TBDMS 2-deoxy-2-(N-benzyloxycarbonylamino)-β-D-glucopyranoside 在 D(+)-10-樟脑磺酸 作用下， 以 乙腈 为溶剂， 反应 18.0h， 以19.8 g的产率得到tert-butyldimethylsilyl 4,6-O-benzylidene-2-(benzyloxycarbonyl)amino-2-deoxy-β-D-glucopyranoside
  参考文献：
  名称：

  Towards a modular synthesis of well-defined chitooligosaccharides: synthesis of the four chitodisaccharides

  摘要：

  The total chemical synthesis of the four well-defined chitodisaccharides is described using N-trichloroacetyl (TCA) and N-benzyloxycarbonyl (Z) as C-2 protecting groups for acetamido and free amino groups, respectively. The synthesis is carried out according to a strategy that paves way to the elaboration of various homo- and hetero-chitooligosaccharides, with perfect control of the number and the position of GIcN and GIcNAc units along the oligomer chain. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.05.010
• 作为产物：
  描述：

  tert-butyldimethylsilyl 3,4,6-tri-O-acetyl-2-(benzyloxycarbonyl)amino-2-deoxy-β-D-glucopyranoside 在 甲醇 、 sodium methylate 作用下， 以96%的产率得到TBDMS 2-deoxy-2-(N-benzyloxycarbonylamino)-β-D-glucopyranoside
  参考文献：
  名称：

  High-Efficiency Synthesis of Chitooligosaccharides

  摘要：

  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。

  DOI：

  10.2174/157017811794557877

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。