5-tert-butyl-2-methylphenyl 3,4,6-tri-O-acetyl-2-(trifluoroacetamido)-2-deoxy-1-thio-β-D-glucopyranoside | 866823-12-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-tert-butyl-2-methylphenyl 3,4,6-tri-O-acetyl-2-(trifluoroacetamido)-2-deoxy-1-thio-β-D-glucopyranoside
• 英文别名: [(2R,3S,4R,5R,6S)-3,4-diacetyloxy-6-(5-tert-butyl-2-methylphenyl)sulfanyl-5-[(2,2,2-trifluoroacetyl)amino]oxan-2-yl]methyl acetate
• CAS: 866823-12-3
• 化学式: C₂₅H₃₂F₃NO₈S
• 分子量: 563.592
• InChiKey: YPOIIJOXQPICDA-FYKMYLNBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  143
• 氢给体数：
  1
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  5-tert-butyl-2-methylphenyl 3,4,6-tri-O-acetyl-2-(trifluoroacetamido)-2-deoxy-1-thio-β-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 乙酸肼 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 22.16h， 生成
  参考文献：
  名称：

  基于酰亚胺酸盐的多天线二等分N-聚糖的高效合成

  摘要：

  在糖蛋白上存在二等分的GlcNAc修饰的N-聚糖的出现对发育和免疫生物学有许多影响。然而，这些特殊的N-聚糖很难从自然界或通过合成获得。我们开发了一种灵活且通用的方法，通过对所有天线采用模块化TFAc保护的供体来合成复杂类型的二等分N-聚糖。TFAc保护的N-聚糖适合于平分GlcNAc的晚期引入。这种综合策略首次允许对单一多酰亚胺N-聚糖及其通过酰亚胺化的二等分衍生物使用单一方法，即使在单罐双糖基化中也具有空前的产量。使用这种新方法，可以容易地获得一分为二的稀有N-聚糖，

  DOI：

  10.1002/anie.201604190
• 作为产物：
  描述：

  1,3,4,6-tetra-O-acetyl-2-deoxy-2-trifluoracetamido-β-D-glucopyranoside 、 5-叔丁基-2-甲基苯硫酚 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到5-tert-butyl-2-methylphenyl 3,4,6-tri-O-acetyl-2-(trifluoroacetamido)-2-deoxy-1-thio-β-D-glucopyranoside
  参考文献：
  名称：

  Convenient Synthesis of an N-Glycan Octasaccharide of the Bisecting Type

  摘要：

  Convenient synthesis of an N-glycan octasaccharide (A) of the bisecting type was described. The stable and easily prepared orthoester F, 3 ''-O-chloroacetyl-4 '',6 ''-O-benzylidene-alpha-D-glucopyranose 1 '',2 ''-(chloromethyl 3',6'-di-O-benzyl-2'-deoxy-2'-phthalimido-beta-D-glucopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosylazide-4'-yl orthoacetate), was designed as the key intermediate with two advantages: (1) distinguishing OH-2 '' from OH-3 '' in beta-D-glucopyranoside to construct the central beta-D-mannopyranoside by inverting the configuration of OH-2 '' in beta-D-glucopyranoside and (2) distinguishing OH-4 '' and OH-6 '' from OH-3 '' in the beta-D-mannopyranoside to introduce the bisecting GlcNAc residue.

  DOI：

  10.1021/jo900016j

文献信息

• Convenient introduction of a bisecting GlcNAc residue into multiantennary N-glycans as the ultimate residue
  作者：Steffen Eller、Claudia Raps、Mathäus Niemietz、Carlo Unverzagt

  DOI：10.1016/j.tetlet.2010.03.031

  日期：2010.5

  A straightforward chemical synthesis was developed for multiantennary N-glycans of the complex-type containing a bisecting GlcNAc moiety. It was found that a bisecting GlcNAc can be introduced as the final residue despite considerable steric hindrance of the buried 4-hydroxyl group of the N-glycan acceptor. This approach circumvents the need for a temporary protecting group on the primary hydroxyl

  已开发出一种简单的化学合成方法，用于包含二等分GlcNAc部分的复杂类型的多天线N-聚糖。已经发现，尽管N-聚糖受体的掩埋的4-羟基具有显着的空间位阻，但是可以将二等分的GlcNAc作为最终残基引入。该方法避免了在中央β-甘露糖苷的伯羟基上需要临时保护基的需要，从而导致了更短和更灵活的合成。因此，具有任选的二等分GlcNAc的N-聚糖的产生可以通过使用相同前体和中间体的统一合成途径来完成。
• Synthesis of a N-glycan nonasaccharide of the bisecting type with additional core-fucose
  作者：Ralf Schuberth、Carlo Unverzagt

  DOI：10.1016/j.tetlet.2005.04.061

  日期：2005.6

  A chemical synthesis was developed for N-glycans substituted with core-fucose and an additional bisecting GlcNAc (LEC10 motif). The synthesis was conducted using a suitably functionalized N-glycan pentasaccharide assembled from modular building blocks. Selective introduction of the bisecting GlcNAc residue was followed by attachment of the alpha 1,6-arm and core-fucose. After introduction of an ammohexanoyl spacer the nonasaccharide was completely deprotected providing a substrate for enzymatic elongation and conjugation to proteins for further biological studies. (c) 2005 Elsevier Ltd. All rights reserved.
• Highly Efficient Synthesis of Multiantennary Bisected N-glycans Based on Imidates
  作者：Manuel Mönnich、Steffen Eller、Theodoros Karagiannis、Lukas Perkams、Thomas Luber、Dimitri Ott、Mathäus Niemietz、Joanna Hoffman、Janika Walcher、Lukas Berger、Matthias Pischl、Markus Weishaupt、Cathrin Wirkner、Rachel G. Lichtenstein、Carlo Unverzagt

  DOI：10.1002/anie.201604190

  日期：2016.8.22

  N‐glycans are suitable for the late introduction of a bisecting GlcNAc. This integrated strategy permits for the first time the use of a single approach for multiantennary N‐glycans as well as their bisected derivatives via imidates, with unprecedented yields even in a one‐pot double glycosylation. With this new method, rare N‐glycans of the bisected type can be obtained readily, thereby providing defined

  在糖蛋白上存在二等分的GlcNAc修饰的N-聚糖的出现对发育和免疫生物学有许多影响。然而，这些特殊的N-聚糖很难从自然界或通过合成获得。我们开发了一种灵活且通用的方法，通过对所有天线采用模块化TFAc保护的供体来合成复杂类型的二等分N-聚糖。TFAc保护的N-聚糖适合于平分GlcNAc的晚期引入。这种综合策略首次允许对单一多酰亚胺N-聚糖及其通过酰亚胺化的二等分衍生物使用单一方法，即使在单罐双糖基化中也具有空前的产量。使用这种新方法，可以容易地获得一分为二的稀有N-聚糖，
• Convenient Synthesis of an <i>N</i>-Glycan Octasaccharide of the Bisecting Type
  作者：Guangfa Wang、Wei Zhang、Zhichao Lu、Peng Wang、Xiuli Zhang、Yingxia Li

  DOI：10.1021/jo900016j

  日期：2009.3.20

  Convenient synthesis of an N-glycan octasaccharide (A) of the bisecting type was described. The stable and easily prepared orthoester F, 3 ''-O-chloroacetyl-4 '',6 ''-O-benzylidene-alpha-D-glucopyranose 1 '',2 ''-(chloromethyl 3',6'-di-O-benzyl-2'-deoxy-2'-phthalimido-beta-D-glucopyranosyl-(1 -> 4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-beta-D-glucopyranosylazide-4'-yl orthoacetate), was designed as the key intermediate with two advantages: (1) distinguishing OH-2 '' from OH-3 '' in beta-D-glucopyranoside to construct the central beta-D-mannopyranoside by inverting the configuration of OH-2 '' in beta-D-glucopyranoside and (2) distinguishing OH-4 '' and OH-6 '' from OH-3 '' in the beta-D-mannopyranoside to introduce the bisecting GlcNAc residue.