2,3,4-tri-O-acetyl-L-rhamnopyranosyl (N-phenyl)-2,2,2-trifluoroacetimidate | 339276-10-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4-tri-O-acetyl-L-rhamnopyranosyl (N-phenyl)-2,2,2-trifluoroacetimidate
• 英文别名: 2,3,4-tri-O-acetyl-L-rhamnopyranosyl trifluoroacetimidate；2,3,4-tri-O-acetyl-L-rhamnopyranosyl (N-phenyl)trifluoroacetimidate；[(2S,3S,4R,5R)-4,5-diacetyloxy-2-methyl-6-[N-phenyl-C-(trifluoromethyl)carbonimidoyl]oxyoxan-3-yl] acetate
• CAS: 339276-10-7
• 化学式: C₂₀H₂₂F₃NO₈
• 分子量: 461.392
• InChiKey: DSNYPEWWBKDGKS-HATYWHASSA-N

物化性质

• 沸点：
  444.1±55.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  32
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  110
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-acetyl-L-rhamnopyranosyl (N-phenyl)-2,2,2-trifluoroacetimidate 在 三氟甲磺酸 、 D(+)-10-樟脑磺酸 、 氢气 、 palladium(II) hydroxide 作用下， 以 四氢呋喃 、 乙醇 、 二氯甲烷 、 乙腈 为溶剂， 生成
  参考文献：
  名称：

  甜叶菊叶中含甜菊糖苷的鼠李糖或木糖的鉴定、化学合成及甜度评价

  摘要：

  从甜叶菊叶中获得的甜菊糖苷越来越多地作为天然低热量甜味剂用于食品工业。其中，由葡萄糖残基组成的主要苷类（如甜菊苷和莱鲍迪苷A）的甜味已被广泛研究。然而，含有鼠李糖或木糖残基的次要天然产物的性质研究很少。在这项研究中，从我们正在发育的甜菊叶中提取了五种未报道的含有鼠李糖或木糖的甜菊糖苷，并评估了它们的甜度。鉴定了高度糖基化的甜菊糖苷，并使用质谱法通过碎片分析检查了它们的结构。这些糖苷的化学合成证实了它们的结构，并允许对少量甜菊醇糖苷进行感官评价。我们的研究表明，一种含木糖的糖苷莱鲍迪甙 FX1 具有均衡的甜味，因此，它是食品工业中使用的天然甜味剂的有前途的候选者。

  DOI：

  10.1021/acs.jafc.3c01753
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-L-rhamnopyranose 、 2,2,2-三氟-N-苯基亚氨代乙酰氯 在 potassium carbonate 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以90%的产率得到2,3,4-tri-O-acetyl-L-rhamnopyranosyl (N-phenyl)-2,2,2-trifluoroacetimidate
  参考文献：
  名称：

  Glycosyl trifluoroacetimidates. Part 1: Preparation and application as new glycosyl donors

  摘要：

  Glycosyl (N-phenyl)trifluoroacetimidates, readily prepared from 1-hydroxyl sugars by treatment with (N-phenyl)trifluoroacetimidoyl chloride in the presence of K2CO3, were demonstrated to be effective glycosyl donors. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(01)00157-5

文献信息

• A set of rhamnosylation-specific antibodies enables detection of novel protein glycosylations in bacteria
  作者：Daniel Gast、Franziska Koller、Ralph Krafczyk、Lukas Bauer、Swetlana Wunder、Jürgen Lassak、Anja Hoffmann-Röder

  DOI：10.1039/d0ob01289k

  日期：——

  Chemical curiosity or not? Specific antibodies to study the rhamnoproteome in bacteria.

  化学好奇心还是没有？特异性抗体用于研究细菌中的rhamnoproteome。
• Efficient synthesis of kaempferol 3,7-O-bisglycosides via successive glycosylation with glycosyl ortho-alkynylbenzoates and trifluoroacetimidates
  作者：Weizhun Yang、Jiansong Sun、Zhongyi Yang、Wei Han、Wei-Dong Zhang、Biao Yu

  DOI：10.1016/j.tetlet.2012.03.103

  日期：2012.5

  Selective glycosylation of the 3-OH of 5,4'-di-O-acetyl-kaempferol was achieved with glycosyl orthoalkynylbenzoates as donors under the catalysis of Ph(3)PALINTf(2), and subsequent glycosylation of the remaining 7-OH with glycosyl trifluoroacetimidates under the catalysis of BF3.OEt2, after global deprotection, afforded the kaempferol 3,7-O-bisglycosides conveniently. (C) 2012 Elsevier Ltd. All rights reserved.
• Glycosyl Trifluoroacetimidates. 2. Synthesis of Dioscin and Xiebai Saponin I
  作者：Biao Yu、Houchao Tao

  DOI：10.1021/jo026103c

  日期：2002.12.1

  Two trisaccharide steroidal saponins, dioscin (1) and Xiebai saponin 1 (2) with various bioactivities, were efficiently synthesized using the newly developed glycosyl N-phenyl trifluoroacetimidates (10-13) as glycosylation donors. Thus, dioscin was synthesized in five steps and a 33% overall yield from diosgenin and glycosyl trifluoroacetimidates (10 and 11). Xiebai saponin I was synthesized in eight steps and a 32% overall yield from laxogenin and glycosyl trifluoroacetimidates (10, 12, and 13), whereupon, the rare steroid laxogenin was prepared from diosgenin in four steps and an overall 69% yield. All the glycosylation reactions involved in the present syntheses demonstrated that glycosyl trifluoroacetimidates were successful donors comparable to the corresponding glycosyl trichloroacetimidates.
• An improved procedure for nucleoside synthesis using glycosyl trifluoroacetimidates as donors
  作者：Jinxi Liao、Jiansong Sun、Biao Yu

  DOI：10.1016/j.carres.2009.03.010

  日期：2009.5

  Using glycosyl trifluoroacetimidates as donors and nitromethane (or acetonitrile) as solvent, silylation and subsequent glycosylation were realized in a 'one-pot' procedure to provide the corresponding nucleosides derivatives in high yields.[GRAPHICS](C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of Anemoclemoside B, the First Natural Product with an Open-Chain Cyclic Acetal Glycosidic Linkage
  作者：Jiansong Sun、Xiuwen Han、Biao Yu

  DOI：10.1021/ol050324y

  日期：2005.5.1

  [GRAPHICS]Anemoclemoside B (1), the first natural product containing a brand-new glycosidic linkage, the open-chain cyclic acetal linkage, was synthesized.