2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->4)-1,2,3,6-tetra-O-benzoyl-D-glucopyranose | 91280-47-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->4)-1,2,3,6-tetra-O-benzoyl-D-glucopyranose
• 英文别名: 1,2,3,6,2',3',4',6'-octa-O-benzoyl-lactose；per-O-benzoylated lactose；1,2,3,6,2’,3’4’,6’-octa-O-benzoyllactose；2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1-4)-1,2,3,6-tetra-O-benzoyl-D-glucopyranose；2,3,4,6-Tetra-O-benzoyl-beta-D-galactopyranosyl-(1->4)-1,2,3,6-tetra-O-benzoyl-D-glucopyranose；[(2R,3R,4S,5R)-4,5,6-tribenzoyloxy-3-[(2S,3R,4S,5S,6R)-3,4,5-tribenzoyloxy-6-(benzoyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl benzoate
• CAS: 91280-47-6
• 化学式: C₆₈H₅₄O₁₉
• 分子量: 1175.17
• InChiKey: KYNIIJHTACNXNG-USJPCQPGSA-N

物化性质

• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.6
• 重原子数：
  87
• 可旋转键数：
  28
• 环数：
  10.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  238
• 氢给体数：
  0
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->4)-1,2,3,6-tetra-O-benzoyl-D-glucopyranose 在 吡啶 、 2,4,6-三甲基吡啶 、 N-溴代丁二酰亚胺(NBS) 、 3 A molecular sieve 、 盐酸羟胺 、 氢溴酸 、 碘 、 一水合肼 、 二乙胺 、 1,1,3,3-四甲基脲 、 sodium iodide 作用下， 以 1,4-二氧六环 、 四氯化碳 、 乙醇 、 水 、 溶剂黄146 、 1,2-二氯乙烷 为溶剂， 反应 114.75h， 生成 methyl hexa-O-benzoyl-α-D-lactosuloside oxime
  参考文献：
  名称：

  Disaccharide-derived 2-oxo- and 2-oximinoglycosyl bromides: novel, conveniently accessible building blocks for the expedient construction of oligosaccharides with .alpha.-D-glucosamine, .beta.-D-mannose, and .beta.-D-mannosamine as constituent sugars

  摘要：

  DOI：

  10.1021/jo00219a017
• 作为产物：
  描述：

  Lactose 生成 2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl-(1->4)-1,2,3,6-tetra-O-benzoyl-D-glucopyranose
  参考文献：
  名称：

  [EN] SYNTHETIC METHODS FOR THE LARGE SCALE PRODUCTION FROM GLUCOSE OF ANALOGS OF SPHINGOSINE, AZIDOSPHINGOSINE, CERAMIDES, LACTOSYL CERAMIDES, AND GLYCOSYL PHYTOSPHINGOSINE
  [FR] METHODES DE SYNTHESE PERMETTANT LA PRODUCTION A GRANDE ECHELLE A PARTIR DE GLUCOSE D'ANALOGUES DE SPHINGOSINE, AZIDOSPHINGOSINE, CERAMIDES, LACTOSYLCERAMIDES, ET GLYCOSYLE PHYTOSPHINGOSINE

  摘要：

  揭示了一种从葡萄糖生产类似物的合成方法，包括鞘氨醇、偶氮鞘氨醇、酰胺、乳糖基酰胺、糖基植物鞘氨醇以及植物鞘氨醇及/或其同系物的对映体衍生物，用于药物应用。所揭示的合成方法简单、直接且易于扩展。

  公开号：

  WO2003101937A1

文献信息

• A new glycosidation method through nitrite displacement on substituted nitrobenzenes
  作者：Xavier Álvarez-Micó、Mario J.F. Calvete、Michael Hanack、Thomas Ziegler

  DOI：10.1016/j.carres.2006.11.017

  日期：2007.2

  protected 1-OH and 1-SH glycoses in the glucose, glucosamine, galactose, mannose, and lactose series react with nitrobenzenes activated by one or two electron withdrawing substituents like nitro and cyano to afford the corresponding aryl glycosides in 50-100% yield. The S(N)Ar displacement of nitrite by 1-OH glycoses is reversible and gives predominantly the alpha-glycosides, whereas 1-SH glycoses do not

  葡萄糖，葡糖胺，半乳糖，甘露糖和乳糖系列中的苄基，苯甲酰基和乙酰基保护的1-OH和1-SH糖基与由一个或两个吸电子取代基（如硝基和氰基）活化的硝基苯反应，得到相应的芳基糖苷50-100％的产率。1-OH糖苷对亚硝酸盐的S（N）Ar置换是可逆的，并且主要产生α-糖苷，而1-SH糖苷则不会发生异化作用而提供β-糖苷。因此，制备的二氰基苯基糖苷是用于通过模板合成制备酞菁-糖缀合物的有用的结构单元。
• [EN] NOVEL SULFATED OLIGOSACCHARIDE DERIVATIVES<br/>[FR] NOUVEAUX DÉRIVÉS D'OLIGOSACCHARIDES SULFATÉS
  申请人：PROGEN PHARMACEUTICALS LTD

  公开号：WO2009049370A1

  公开（公告）日：2009-04-23

  The invention relates to novel compounds that have utility as inhibitors of heparan sulfate-binding proteins; compositions comprising the compounds, and use of the compounds and compositions thereof for the antiangiogenic, antimetastatic, anti-inflammatory, antimicrobial, anticoagulant and/or antithrombotic treatment of a mammalian subject.

  这项发明涉及具有作为肝素硫酸结合蛋白抑制剂的效用的新化合物；包含这些化合物的组合物；以及利用这些化合物和组合物对哺乳动物主体进行抗血管生成、抗转移、抗炎、抗微生物、抗凝血和/或抗血栓治疗的用途。
• AuBr₃-catalyzed azidation of per-<i>O</i>-acetylated and per-<i>O</i>-benzoylated sugars
  作者：Jayashree Rajput、Srinivas Hotha、Madhuri Vangala

  DOI：10.3762/bjoc.14.56

  日期：——

  Herein we report, for the first time, the successful anomeric azidation of per-O-acetylated and per-O-benzoylated sugars by catalytic amounts of oxophilic AuBr₃ in good to excellent yields. The method is applicable to a wide range of easily accessible per-O-acetylated and per-O-benzoylated sugars. While reaction with per-O-acetylated and per-O-benzoylated monosaccharides was complete within 1–3 h at room temperature, the per-O-benzoylated disaccharides needed 2–3 h of heating at 55 °C.

  在这里，我们首次报道了对经过O-乙酰化和O-苯甲酰化的糖进行顺式异构体化合成的成功实例，通过使用催化量的亲氧化金Br₃，产率良好至优良。该方法适用于广泛易得的O-乙酰化和O-苯甲酰化糖。虽然与O-乙酰化和O-苯甲酰化的单糖在室温下1-3小时内反应完成，但O-苯甲酰化的二糖需要在55°C下加热2-3小时。
• Synthesis and Antitumor Activity of a New Ergosterol Derivative
  作者：Zhen-Yuan Zhu、Zhen-qian Wang、Fei Liu、Xiao-Cui Liu、Li-Jing Chen、Xiao-Ran Ge、An-Jun Liu、Yong-Min Zhang

  DOI：10.1007/s10600-016-1607-6

  日期：2016.3

  ranosyl-(1→4)-β-D-glucopyranoside) was efficiently synthesized and evaluated for its inhibitory activities against S180 cell lines compared with ergosterol. The structures of all synthesized compounds were fully characterized by spectroscopic data (NMR, MS). The antitumor activity of the new derivative was significantly enhanced compared with ergosterol.

  Ergosterol-3-O-(β-D-吡喃半乳糖基-(1→4)-β-D-吡喃葡萄糖苷)被有效合成并评估其对S180细胞系的抑制活性与麦角固醇相比。所有合成化合物的结构都通过光谱数据（NMR、MS）进行了充分表征。与麦角甾醇相比，新衍生物的抗肿瘤活性显着增强。
• Streamlined chemoenzymatic total synthesis of prioritized ganglioside cancer antigens
  作者：Hai Yu、Abhishek Santra、Yanhong Li、John B. McArthur、Tamashree Ghosh、Xiaoxiao Yang、Peng G. Wang、Xi Chen

  DOI：10.1039/c8ob01087k

  日期：——

  A highly efficient streamlined chemoenzymatic strategy for total synthesis of four prioritized ganglioside cancer antigens GD2, GD3, fucosyl GM1, and GM3 from commercially available lactose and phytosphingosine is demonstrated. Lactosyl sphingosine (LacβSph) was chemically synthesized (on a 13 g scale), subjected to sequential one-pot multienzyme (OPME) glycosylation reactions with facile C18-cartridge

  展示了一种高效的简化化学酶策略，可从市售乳糖和植物鞘氨醇中合成四种优先神经节苷脂类癌抗原GD2，GD3，岩藻糖基GM1和GM3。化学合成了乳糖基鞘氨醇（LacβSph）（13 g规模），进行了连续一锅多酶（OPME）糖基化反应，并进行了简便的C18碳粉纯化，然后改善了酰化条件，形成了目标神经节苷脂，包括岩藻糖基GM1，以前从未合成过。