allyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside | 866325-70-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside
• 英文别名: [(2R,3R,4S,5R,6R)-4,5-dibenzoyloxy-2-(hydroxymethyl)-6-prop-2-enoxyoxan-3-yl] benzoate
• CAS: 866325-70-4
• 化学式: C₃₀H₂₈O₉
• 分子量: 532.547
• InChiKey: CVVKCLAZIXFXMQ-YFIKXWTHSA-N

物化性质

• 熔点：
  114.0-115.8 °C(Solv: hexane (110-54-3); ethyl acetate (141-78-6))
• 沸点：
  679.7±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  39
• 可旋转键数：
  13
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  allyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside 在 lithium acetate 、 sodium methylate 、 copper diacetate 、 silver trifluoromethanesulfonate 、 palladium diacetate 、 1,1,3,3-四甲基脲 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 14.0h， 生成 络塞维
  参考文献：
  名称：

  Synthesis of Rosavin and its analogues based on a Mizoroki-Heck type reaction

  摘要：

  The Rosavin framework could be constructed with either phenylboronic acids, the protected arabinopyranosyl bromide 4 or the protected xylopyranosyl bromide 5, along with allyl O-beta-D-glucopyranoside 7 that could be easily prepared based on direct beta-glucosidation between allyl alcohol and D-glucose using the immobilized beta-glucosidase (EC 3.2.1.21). The key reaction was the Pd(II)-catalyzed Mizoroki-Heck type reaction between allyl beta-D-glucopyranoside congeners 9 or 10 and arylboronic acids. Deprotection of the coupling products afforded synthetic Rosavin 1, 4-methoxycinnamyl 6-O-(alpha-L-arabinopyranosyl)-beta-D-glucopyranoside 2, and cinnamyl 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyrano side 3, which were identical with the natural products in respect to the specific rotation and spectral data. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.06.040
• 作为产物：
  描述：

  Acetic acid (2R,3R,4S,5R,6R)-3,5-diacetoxy-2-acetoxymethyl-6-allyloxy-tetrahydro-pyran-4-yl ester 在 吡啶 、 四丁基氟化铵 、 sodium methylate 、 溶剂黄146 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 1.0h， 生成 allyl 2,3,4-tri-O-benzoyl-β-D-glucopyranoside
  参考文献：
  名称：

  通过使用TiCl4的酰化叠氮化物和苯甲酰化二糖的区域专一性化。

  摘要：

  当路易斯酸（例如TiCl 4或SnCl 4）与吡喃糖环的氧原子和另一个位点配位时，会促进螯合诱导的异构化，从而导致内环裂解和异构化为更稳定的异构体。在这项研究中，证明了区域特异性定点异构化。的TiCl 4（2.5当量）用于诱导15种反应性低的糖基叠氮化物和二糖底物的异构化，并获得高产率（＞ 75％）和立体选择性（α/β＞ 9∶1）。实例包括吡喃葡萄糖醛酸，吡喃葡萄糖醛酸和甘露吡喃醛酸酯以及N-乙酰化吡喃葡萄糖醛酸和吡喃葡萄糖醛酸酯衍生物。包括在聚半乳糖醛酸中发现的具有α1→4键的二糖。已发现使用苯甲酰化的糖类在二糖异构化中非常重要，因为尝试使相关的乙酰基保护的2,3-碳酸酯保护的衍生物异构化的尝试并不成功。

  DOI：

  10.1002/chem.201302572

文献信息

• Total Synthesis of Marine Glycosphingolipid Vesparioside B
  作者：Peng-Cheng Gao、San-Yong Zhu、Hui Cao、Jin-Song Yang

  DOI：10.1021/jacs.5b12589

  日期：2016.2.10

  The first total synthesis of a major component of marine glycolipid vesparioside B ( Scheme 1 , 1, R1 = n-C22H45, R2 = n-C14H29) has been accomplished through a convergent [4 + 3] coupling strategy. Key steps included stereoselective installment of a set of challenging 1,2-cis-glycoside bonds. A 2-quinolinecarbonyl-assisted α-galactosylation and a novel β-arabinosylation were developed, respectively

  海洋糖脂 vesparioside B 的主要成分的首次全合成（方案 1, 1, R1 = n-C22H45, R2 = n-C14H29）已通过收敛 [4 + 3] 耦合策略完成。关键步骤包括立体选择性安装一组具有挑战性的 1,2-顺式糖苷键。分别开发了 2-喹啉羰基辅助的 α-半乳糖基化和新型 β-阿拉伯糖基化，以合成 α-呋喃半乳糖苷和 β-阿拉伯吡喃糖苷键。此外，4,6-O-亚苄基控制的α-吡喃半乳糖基化反应允许左侧四糖供体2与右侧二糖脂质受体3有效连接，从而导致1的全合成。
• [EN] β-1,6-GLUCAN CETUXIMAB ANTIBODY CONJUGATES<br/>[FR] CONJUGUÉS DE Β-1,6-GLUCANE ET DE L'ANTICORPS CÉTUXIMAB
  申请人：IMMUNEXCITE INC

  公开号：WO2016196682A1

  公开（公告）日：2016-12-08

  The present invention encompasses embodiments in which cetuximab or a related cetuximab antibody is conjugated to β-1,6-glucan oligomers. Thus, the present invention includes, among other things, compositions including cetuximab conjugated to one or more β-1,6-glucan oligomers. The present invention further includes, among other things, methods of making and/or using such β-1,6-glucan conjugates. In certain embodiments, a β-1,6-glucan conjugate of the present invention is useful as a therapeutic or in a method of therapy.

  本发明涵盖了将Cetuximab或相关的Cetuximab抗体与β-1,6-葡聚糖寡聚体结合的实施例。因此，本发明包括将Cetuximab与一个或多个β-1,6-葡聚糖寡聚体结合的组合物，以及制备和/或使用这样的β-1,6-葡聚糖结合物的方法等。在某些实施例中，本发明的β-1,6-葡聚糖结合物可用作治疗或治疗方法中的治疗剂。
• DAST-Mediated Regioselective Anomeric Group Migration in Saccharides
  作者：Po-Chiao Lin、Avijit Kumar Adak、Shau-Hua Ueng、Li-De Huang、Kuo-Ting Huang、Ja-an Annie Ho、Chun-Cheng Lin

  DOI：10.1021/jo900516r

  日期：2009.6.5

  When saccharides bearing a sulfur, selenium, or oxygen substituent at the anomeric center and an unprotected hydroxyl group either at C-4 or C-6 were subjected to fluorination with DAST in dichloromethane, a regioselective migration of the anomeric substituent to the C-4 or C-6 position was observed. Certain saccharides gave a mixture of migration and normal fluorination products whereas others yielded mainly or exclusively migration products (beta-glycosyl fluorides). The high thermal and chemical stability of migrated glycosyl fluorides were demonstrated to be an important precursor for many significant carbohydrate analogies. It is therefore suggested that these migrations may have useful applications in organic synthesis.
• Regiospecific Anomerisation of Acylated Glycosyl Azides and Benzoylated Disaccharides by Using TiCl₄
  作者：Mark Farrell、Jian Zhou、Paul V. Murphy

  DOI：10.1002/chem.201302572

  日期：2013.10.25

  5 equiv) was employed to induce anomerisation of 15 glycosyl azide and disaccharide substrates of low reactivity, and high yields (>75 %) and stereoselectivies (α/β>9:1) were achieved. The examples included glucopyranuronate, galactopyranuronate and mannopyranuronate as well as N‐acetylated glucopyranuronate and galactopyranuronate derivatives. A disaccharide with the α1→4 linkage found in polygalacturonan

  当路易斯酸（例如TiCl 4或SnCl 4）与吡喃糖环的氧原子和另一个位点配位时，会促进螯合诱导的异构化，从而导致内环裂解和异构化为更稳定的异构体。在这项研究中，证明了区域特异性定点异构化。的TiCl 4（2.5当量）用于诱导15种反应性低的糖基叠氮化物和二糖底物的异构化，并获得高产率（＞ 75％）和立体选择性（α/β＞ 9∶1）。实例包括吡喃葡萄糖醛酸，吡喃葡萄糖醛酸和甘露吡喃醛酸酯以及N-乙酰化吡喃葡萄糖醛酸和吡喃葡萄糖醛酸酯衍生物。包括在聚半乳糖醛酸中发现的具有α1→4键的二糖。已发现使用苯甲酰化的糖类在二糖异构化中非常重要，因为尝试使相关的乙酰基保护的2,3-碳酸酯保护的衍生物异构化的尝试并不成功。
• Synthesis of Rosavin and its analogues based on a Mizoroki-Heck type reaction
  作者：Msashi Kishida、Hiroyuki Akita

  DOI：10.1016/j.tetasy.2005.06.040

  日期：2005.8

  The Rosavin framework could be constructed with either phenylboronic acids, the protected arabinopyranosyl bromide 4 or the protected xylopyranosyl bromide 5, along with allyl O-beta-D-glucopyranoside 7 that could be easily prepared based on direct beta-glucosidation between allyl alcohol and D-glucose using the immobilized beta-glucosidase (EC 3.2.1.21). The key reaction was the Pd(II)-catalyzed Mizoroki-Heck type reaction between allyl beta-D-glucopyranoside congeners 9 or 10 and arylboronic acids. Deprotection of the coupling products afforded synthetic Rosavin 1, 4-methoxycinnamyl 6-O-(alpha-L-arabinopyranosyl)-beta-D-glucopyranoside 2, and cinnamyl 6-O-(beta-D-xylopyranosyl)-beta-D-glucopyrano side 3, which were identical with the natural products in respect to the specific rotation and spectral data. (c) 2005 Elsevier Ltd. All rights reserved.