D-glycero-D-galacto-heptose

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: D-glycero-D-galacto-heptose
• 英文别名: D-glycero-D-galacto-heptopyranose；(3R,4S,5R,6R)-6-[(1R)-1,2-dihydroxyethyl]oxane-2,3,4,5-tetrol
• 化学式: C₇H₁₄O₇
• 分子量: 210.184
• InChiKey: BGWQRWREUZVRGI-ZMKYHYQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  131
• 氢给体数：
  6
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  D-glycero-D-galacto-heptose 生成 Hexa-O-acetyl-β-D-glycero-D-gulo-heptopyranose
  参考文献：
  名称：

  合成L-甘油-D-甘露庚糖

  摘要：

  2,3-：5,6-二-O-异亚丙基-D-甘露聚糖与2-lithio-1,3-dithiane的链扩展立体选择性地产生D-甘油-D-半乳糖-庚糖的衍生物。通过醛功能的降低和7-OH基团的氧化将庚糖转化为D-甘油-D-甘露聚糖-庚糖。

  DOI：

  10.1016/s0040-4039(00)89224-2
• 作为产物：
  描述：

  D-甘露糖 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 甲醇 、 水 为溶剂， 生成 D-glycero-D-galacto-heptose
  参考文献：
  名称：

  从 D-甘露糖中方便地合成 3-Deoxy-D-manno-2-octulosonic Acid (KDO) 和 3-Deoxy-D-glycero-D-galacto-2-nonulosonic Acid (KDN) 衍生物

  摘要：

  4-O-苄基-2,3:5,6-二-O-异亚丙基-D-甘露糖和2,3,4,5,6,7-六-O-苄基-6-D的Horner-Wittig反应-glycero-2,3,4,5-D-galacto-heptose 与 2-benzyloxycarbonylamino-2-(diethoxyphosphoryl) 乙酸甲酯分别以良好的产率得到相应的 α-脱氢氨基酸衍生物。它们被转化为甲基 3-deoxy-4,5:7,8-di-O-isopropylidene-α-D-manno-2-octulopyranosonate 和甲基 (methyl 3-deoxy-D-glycero-β-D-galacto- 2-nonulopyranosid)onate 通过 α-氧代链烷酸甲酯衍生物。

  DOI：

  10.1246/cl.1994.129

文献信息

• Conversion of Unprotected Aldose Sugars to Polyhydroxyalkyl and <i>C</i>-Glycosyl Furans via Zirconium Catalysis
  作者：Nima Ronaghi、David M. Fialho、Christopher W. Jones、Stefan France

  DOI：10.1021/acs.joc.0c02176

  日期：2020.12.4

  An efficient, zirconium-catalyzed conversion of unprotected aldose sugars with acetylacetone to polyhydroxyalkyl furans or C-glycosylfurans is reported. The furan products are formed in up to 93% yield using 5–10 mol % ZrCl4. Pentoses are readily converted at room temperature, while hexoses and their oligosaccharides require mild heating (i.e., 50 °C). Efficient conversions of glycolaldehyde, glyceraldehyde

  据报道，未保护的醛糖与乙酰丙酮的有效锆催化转化为聚羟烷基呋喃或C-糖基呋喃。使用5–10 mol％ZrCl 4可以高达93％的产率形成呋喃产物。戊糖在室温下易于转化，而己糖及其寡糖则需要适度加热（即50°C）。还证明了乙醇醛，甘油醛，赤藓糖，庚糖和葡萄糖胺的有效转化。该方法至少在以下方面之一超越了先前的路易斯酸催化方法中的每一种：（i）较低的催化剂负载量；（ii）降低反应温度；（iii）缩短反应时间；（iv）等摩尔底物化学计量；（v）扩大食糖范围；（vi）更高的选择性；（vii）使用富含地球的Zr催化剂。
• The Amadori rearrangement as glycoconjugation method: Synthesis of non-natural <i>C</i>-glycosyl type glycoconjugates
  作者：Katharina Gallas、Gerit Pototschnig、Florian Adanitsch、Arnold E Stütz、Tanja M Wrodnigg

  DOI：10.3762/bjoc.8.185

  日期：——

  The Amadori rearrangement was investigated as a potential method for the conjugation of carbohydrate moieties to suitable amino components. Starting from selected aldoheptoses, which are readily available by means of the Kiliani-Fischer C-elongation reaction of the corresponding aldohexoses, glycoconjugates presenting D-gluco, D-manno and D-galacto as well as GlcNAc motifs have been synthesised. Following

  研究了 Amadori 重排作为碳水化合物部分与合适的氨基组分缀合的潜在方法。从选定的己醛糖开始，它们很容易通过相应的己醛糖的 Kiliani-Fischer C 延伸反应获得，已经合成了呈现 D-葡萄糖、D-甘露糖和 D-半乳糖以及 GlcNAc 基序的糖缀合物。遵循这一策略，可以通过非常短的合成方法获得非天然 C-糖基型糖缀合物，可用作较大分子结构的组成部分。
• The Amadori Rearrangement for Carbohydrate Conjugation: Scope and Limitations
  作者：Cornelia Hojnik、Anne Müller、Tobias-Elias Gloe、Thisbe K. Lindhorst、Tanja M. Wrodnigg

  DOI：10.1002/ejoc.201600458

  日期：2016.9

  The Amadori rearrangement was investigated for the synthesis of C‐glycosyl‐type neoglycoconjugates. Various amines including diamines, amino‐functionalized glycosides, lysine derivatives, and peptides were conjugated with two different heptoses to generate non‐natural C‐glycosyl‐type glycoconjugates of the d‐gluco and d‐manno series. With these studies, the scope and limitations of the Amadori rearrangement

  研究了 Amadori 重排以合成 C-糖基型新糖缀合物。包括二胺、氨基功能化糖苷、赖氨酸衍生物和肽在内的各种胺与两种不同的庚糖结合，生成 d-gluco 和 d-manno 系列的非天然 C-糖基型糖缀合物。通过这些研究，Amadori 重排作为结合方法的范围和局限性已经在碳水化合物底物和氨基成分方面得到了举例说明。
• Are D-<i>manno</i>-configured Amadori products ligands of the bacterial lectin FimH?
  作者：Tobias-Elias Gloe、Insa Stamer、Cornelia Hojnik、Tanja M Wrodnigg、Thisbe K Lindhorst

  DOI：10.3762/bjoc.11.123

  日期：——

  The Amadori rearrangement was employed for the synthesis of C-glycosyl-type D-mannoside analogues, namely 1-propargylamino- and 1-phenylamino-1-deoxy-α-D-manno-heptopyranose. They were investigated as ligands of type 1-fimbriated E. coli bacteria by means of molecular docking and bacterial adhesion studies. It turns out that Amadori rearrangement products have a limited activity as inhibitors of bacterial adhesion because the β-C-glycosidically linked aglycone considerably hampers complexation within the carbohydrate binding site of the type 1-fimbrial lectin FimH.

  Amadori重排法被用于合成C-糖基型D-甘露聚糖类似物，即1-丙炔氨基-和1-苯胺基-1-去氧-α-D-甘露-庚呋醇。通过分子对接和细菌粘附研究，它们被作为1-纤毛E. coli细菌的配体进行了研究。结果表明，Amadori重排产物作为细菌粘附抑制剂的活性有限，因为β-C-糖苷键连接的无糖基团在1-纤毛凝集素FimH的糖基结合位点内显著阻碍了复合作用。
• Hydroxyl group orientation affects hydrolysis rates of methyl α-septanosides
  作者：Shankar D. Markad、Shawn M. Miller、Martha Morton、Mark W. Peczuh

  DOI：10.1016/j.tetlet.2009.12.109

  日期：2010.2

  Hydrolysis rates for three related methyl α-septanosides were obtained. The septanosides were synthesized via mCPBA epoxidation and methanolysis of d-mannose, d-galactose, and d-glucose-based oxepines. The rate of hydrolysis correlates with the orientation of hydroxyl groups on the septanose ring in a manner analogous to pyranosides.

  获得了三种相关的甲基α-septanosides的水解速率。所述septanosides分别通过合成米CPBA环氧化和甲醇分解的d甘露糖，d半乳糖，和ð葡萄糖为基础的oxepines。水解速率以类似于吡喃糖苷的方式与琼脂糖环上羟基的取向相关。