p-methoxyphenyl α-D-rhamnopyranoside | 934587-87-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: p-methoxyphenyl α-D-rhamnopyranoside
• 英文别名: 4-methoxyphenyl 1-α-D-rhamnopyranoside；(2R,3S,4S,5S,6R)-2-(4-methoxyphenoxy)-6-methyloxane-3,4,5-triol
• CAS: 934587-87-8
• 化学式: C₁₃H₁₈O₆
• 分子量: 270.282
• InChiKey: QYXDZVRPDLEXIN-FOZMMYHZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  88.4
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  p-methoxyphenyl α-D-rhamnopyranoside 在 吡啶 、 二正丁基氧化锡 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 34.0h， 生成 [(2R,3R,4S,5S,6R)-5-benzoyloxy-6-(4-methoxyphenoxy)-2-methyl-4-phenylmethoxyoxan-3-yl] benzoate
  参考文献：
  名称：

  实用合成有价值的鼠李糖苷寡糖合成原料

  摘要：

  已经开发了d-鼠李糖苷的有效合成及其区域选择性保护和去保护的相应方法，以便为针对细菌感染的疫苗的复杂寡糖合成提供关键的组成部分。

  DOI：

  10.1016/j.tetlet.2007.01.122
• 作为产物：
  描述：

  Α-D-五乙酸甘露糖酯 在 吡啶 、 甲醇 、 三氟化硼乙醚 、 sodium methylate 、 对甲苯磺酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 26.0h， 生成 p-methoxyphenyl α-D-rhamnopyranoside
  参考文献：
  名称：

  由吡喃糖苷 2,4-双三氟甲磺酸酯一锅法偶然合成手性二烯

  摘要：

  L-鼠李糖基2,4-双三氟甲磺酸酯的尝试亲核置换导致通过竞争性级联消除偶然形成手性二烯。该反应也遵循与d-鼠李糖基和d-甘露糖基 2,4-二三氟甲磺酸酯底物相同的途径，提供了具有相反立体化学的二烯。该反应可能通过 C2 三氟甲磺酸酯的E 2 消除进行，然后进行烯丙基重排。易于获得的手性二烯可用于天然产物的合成。

  DOI：

  10.1016/j.carres.2021.108351

文献信息

• En route to a carbohydrate-based vaccine against Burkholderia cepacia
  作者：Régis Fauré、Tze Chieh Shiao、David Lagnoux、Denis Giguère、René Roy

  DOI：10.1039/b708365c

  日期：——

  We report a very high yielding first total synthesis of trisaccharide 5, α-D-Rhap-(1→3)-α-D-Rhap-(1→4)-α-D-Galp, corresponding to the repeating unit 1 of an O-polysaccharide present in the lipopolysaccharide of clinical isolate of Burkholderia cepacia. The approach included two successive glycosylations, based on D-rhamnosyl trichloroacetimidate donors 12 and 14. The oligosaccharide5 has been further functionalized by photochemical coupling or cross-metathesis with non-natural amino acid derivatives. Trisaccharidylamino acids 16 and 17 are now available, with the aim of preparing a novel synthetic carbohydrate-based vaccine.

  我们首次成功合成了三糖5，α-D-Rhap-(1→3)-α-D-Rhap-(1→4)-α-D-Galp，其产量非常高，与伯克霍尔德氏菌临床分离株脂多糖中O-多糖的重复单元1相对应。该方法包括基于D-鼠李糖基三氯乙酰亚胺供体12和14的两次连续糖基化。通过光化学偶联或与非天然氨基酸衍生物的交叉复分解，寡糖5进一步被官能化。三糖基氨基酸16和17现已可用，目的是制备一种新型的合成碳水化合物疫苗。
• Synthesis of 6-Deoxy-D-altrose Used as an Authentic Sample to Identify an Unknown Monosaccharide Isolated from the Fruiting Body of an Edible Mushroom
  作者：Hideharu Ishida、Masashi Yamada、Fumi Yoshida、Hiromune Ando、Makoto Kiso、Masakuni Tako

  DOI：10.3987/com-10-s(e)107

  日期：——

  Here, we describe the synthesis of 6-deoxy-D-altrose and its subsequent use as an authentic sample to verify the structure of a monosaccharide newly isolated from the fruiting body of an edible mushroom. D-Rhamnopyranoside, converted from D-mannopyranoside, was selectively protected to give the 3-OH derivative, which was converted to the corresponding 6-deoxy-D-altropyranoside by nucleophilic substitution of the 3-triflate with acetoxy group. Removal of the protecting group, including the temporary protection of the anomeric position with the THP group, afforded the desired 6-deoxy-D-altrose. Both the NMR data and the [alpha](D) value were identical to the data on the natural product, thus indicating that the recently isolated monosaccharide was 6-deoxy-D-altrose.
• Brønsted Acid-Promoted Glycosylations of Disaccharide Glycal Substructures of the Saccharomicins
  作者：Bradley R. Balthaser、Frank E. McDonald

  DOI：10.1021/ol901923x

  日期：2009.11.5

  An acid-promoted glycosylation and alkynol cycloisomerization sequence provided direct access to the 2-deoxytrisaccharide corresponding to the fucose-saccharosamine-digitoxose substructure of saccharomicin B. In the course of this work, the absolute stereochemistry of the repeating fucose-saccharosamine disaccharide of saccharomicins was also confirmed.
• Practical synthesis of valuable d-rhamnoside building blocks for oligosaccharide synthesis
  作者：Régis Fauré、Tze Chieh Shiao、Sonia Damerval、René Roy

  DOI：10.1016/j.tetlet.2007.01.122

  日期：2007.3

  The efficient synthesis of d-rhamnoside and the corresponding methods for its regioselective protections and deprotections have been developed in order to provide key building blocks for complex oligosaccharide syntheses toward vaccines against bacterial infections.

  已经开发了d-鼠李糖苷的有效合成及其区域选择性保护和去保护的相应方法，以便为针对细菌感染的疫苗的复杂寡糖合成提供关键的组成部分。
• Serendipitous one-pot synthesis of chiral dienes from pyranosidic 2,4-bistriflates
  作者：Diksha Rai、Someswara Rao Sanapala、Suvarn S. Kulkarni

  DOI：10.1016/j.carres.2021.108351

  日期：2021.7

  Attempted nucleophilic displacements of l-rhamnosyl 2,4-bistriflates led to serendipitous formation of a chiral diene via competing cascade eliminations. The reaction also followed the same pathway with d-rhamnosyl and d-mannosyl 2,4-bistriflates substrates providing access to dienes with opposite stereochemistry. The reaction presumably proceeds through E2 elimination of C2 triflate followed by allylic

  L-鼠李糖基2,4-双三氟甲磺酸酯的尝试亲核置换导致通过竞争性级联消除偶然形成手性二烯。该反应也遵循与d-鼠李糖基和d-甘露糖基 2,4-二三氟甲磺酸酯底物相同的途径，提供了具有相反立体化学的二烯。该反应可能通过 C2 三氟甲磺酸酯的E 2 消除进行，然后进行烯丙基重排。易于获得的手性二烯可用于天然产物的合成。