2,3,4,6-tetra-O-benzoyl-D-galactopyranosyl trichloroacetimidate | 203435-09-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4,6-tetra-O-benzoyl-D-galactopyranosyl trichloroacetimidate
• 英文别名: [(2R,3S,4S,5R)-3,4,5-tribenzoyloxy-6-(2,2,2-trichloroethanimidoyl)oxyoxan-2-yl]methyl benzoate
• CAS: 203435-09-0
• 化学式: C₃₆H₂₈Cl₃NO₁₀
• 分子量: 740.978
• InChiKey: KTHFOWIANASXOK-FBGIRCPFSA-N

物化性质

• 沸点：
  758.7±70.0 °C(Predicted)
• 密度：
  1.40±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.2
• 重原子数：
  50
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  148
• 氢给体数：
  1
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2,3,4,6-tetra-O-benzoyl-D-galactopyranosyl trichloroacetimidate 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 5.0h， 生成 ergosterol-3-O-β-D-galactopyranoside
  参考文献：
  名称：

  Highly efficient synthesis and antitumor activity of monosaccharide saponins mimicking components of Chinese folk medicineCordyceps sinensis

  摘要：

  Ergosterol 3-O-beta-D-glucopyranoside (1a) and ergosterol 3-O-beta-D-galactopyranoside (1b) were highly efficiently synthesized and evaluated for their inhibitory activities against two tumor cell lines. The structures of these compounds were extensively confirmed by H-1, C-13 NMR, IR, and HRMS. Compounds 1a and 1b exhibited interesting cytotoxic profiles. The antitumor activity of compound 1a was higher than that of 1b.

  DOI：

  10.1080/10286020.2012.670220
• 作为产物：
  描述：

  alpha-D-半乳糖 在 吡啶 、 N-溴代丁二酰亚胺(NBS) 、 偶氮二异丁腈 、 水 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 乙酰氯 作用下， 以 二氯甲烷 为溶剂， 反应 1.17h， 生成 2,3,4,6-tetra-O-benzoyl-D-galactopyranosyl trichloroacetimidate
  参考文献：
  名称：

  无四氯化碳的烯丙基卤化介导的烯丙基糖苷糖基化

  摘要：

  烯丙基糖苷的烯丙基溴化使用 NBS/AIBN 试剂在 (EtO) 2 CO 和 PhCF 3溶液中进行，不使用 CCl 4作为溶剂。活化的混合卤代烯丙基糖苷导致糖基化，由三氟甲磺酸酯介导，以潜在活性的方式，烯丙基糖苷充当供体和受体。使用不同的三氟甲磺酸酯启动子、非糖基受体和各种烯丙基糖基供体进行系统糖基化研究。在 PhCF 3溶液中开发了一锅烯丙基卤化和随后的糖基化。这种较新的糖基化方法用于获得木糖-吡喃糖苷二糖和三糖。

  DOI：

  10.1039/d1ob01298c

文献信息

• Synthesis of a chlorogenin glycoside library using an orthogonal protecting group strategy
  作者：Ying-Hsin Wang、Hsien-Wei Yeh、Hsiao-Wen Wang、Chia-Chun Yu、Jih-Hwa Guh、Der-Zen Liu、Pi-Hui Liang

  DOI：10.1016/j.carres.2013.04.022

  日期：2013.6

  Naturally occurring spirostanol saponins bear a chacotriose, alpha-L-rhamnopyranosyl-(1-->2)-[alpha-L-rhamnopyranosyl-(1-->4)]-beta-D-glucopyr anose residue as the oligosaccharide moiety which is believed to be important for biological activity. Herein the development of a concise, combinatorial method for the synthesis of two series of glycan variants at the 2' and/or 4' positions of chacotriose is

  天然存在的螺固醇皂苷带有低聚部分的三甘醇，α-L-鼠李糖基-（1-> 2）-[α-L-鼠李糖基-（1-> 4）]-β-D-葡萄糖吡喃糖残基。据信对于生物学活性是重要的。在本文中，描述了一种简明的组合方法的开发，该方法用于合成在chacotriose的2'和/或4'位置上的两个系列的聚糖变体，并研究了叶绿素在3-OH处的糖苷部分的结构-活性关系。发现这些化合物对白血病细胞系CCRF和HL-20的细胞毒性较弱，表明茶三糖部分对于抗癌活性很重要。
• Glycosylation of a Ketone with an <i>O</i>-Glycosyl Trichloroacetimidate Provides an Enol Glycoside
  作者：Xianglai Liu、Sumei Ren、Qi Gao、Chun Hu、Yingxia Li、Ning Ding

  DOI：10.1021/acs.orglett.8b02126

  日期：2018.9.7

  An enol-type glycosylation reaction has been investigated. Enol glycosides can be obtained from the reaction between O-glycosyl trichloroacetimidates and the corresponding ketones promoted by an acid. The enol glycosides derived from cyclic ketones can be afforded efficiently and isolated in good yield, while those from acyclic ketones are prepared in low conversion or are too labile for isolation

  已经研究了烯醇型糖基化反应。烯醇糖苷可以从O-糖基三氯乙亚氨酸酯与相应的由酸促进的酮之间的反应中获得。可以有效地提供衍生自环状酮的烯醇糖苷并以高收率分离，而衍生自无环酮的烯醇糖苷转化率低或太不稳定而无法分离。对不同糖基供体类型的进一步研究表明，只有O-糖基三氯乙酰亚氨酸酯可以很好地用作烯醇糖基化的供体。
• TRITERPENES DERIVATIVES AND USES THEREOF AS ANTITUMOR AGENTS OR ANTI-INFLAMMATORY AGENTS
  申请人：PICHETTE ANDRE

  公开号：US20080167254A1

  公开（公告）日：2008-07-10

  A compound of formula (1): wherein R 1 is selected from the group consisting of H, α-L-Rhamnopyranose, α-D-Mannopyranose, β-D-Xylopyranose, β-D-Glucopyranose, and α-D-Arabinopyranose; R 2 is selected from CH 3 , COOH, CH 2 OH, COOCH 3 and CH 2 O-α-D-Arabinopyranose; with the proviso that the compound of formula (I) is not a compound of formula (I) wherein R 1 is β-D-Glucopyranose and R 2 is COOH; wherein R 1 is α-L-Rhamnopyranose and R 2 is CH 3 ; wherein R 1 is β-D-Glucopyranose and R 2 is CH 2 OH; wherein R 1 is β-D-Xylopyranose and R 2 is CH 2 OH; wherein R 1 is α-L-Rhamnopyranose and R 2 is COOCH 3 , wherein R 1 is H and R 2 is CH 3 ; wherein R 1 is H and R 2 is CH 2 OH; wherein R 1 is H and R 2 is COOH; or wherein R 1 is H and R 2 is COOCH 3 , or a pharmaceutically acceptable salt thereof.

  式（1）的化合物：其中R1选自H、α-L-葡萄糖苷、α-D-甘露糖苷、β-D-木糖苷、β-D-葡萄糖苷和α-D-阿拉伯糖苷组成的群；R2选自CH3、COOH、CH2OH、COOCH3和CH2O-α-D-阿拉伯糖苷；但化合物的式（I）不是式（I）中R1为β-D-葡萄糖苷且R2为COOH的化合物；其中R1为α-L-葡萄糖苷且R2为CH3；其中R1为β-D-葡萄糖苷且R2为CH2OH；其中R1为β-D-木糖苷且R2为CH2OH；其中R1为α-L-葡萄糖苷且R2为COOCH3；其中R1为H且R2为CH3；其中R1为H且R2为CH2OH；其中R1为H且R2为COOH；或其中R1为H且R2为COOCH3，或其药学上可接受的盐。
• Synthesis of the Cytotoxic Gitogenin 3β-<i>O</i>-[2-<i>O</i>-(α-l-Rhamnopyranosyl)-β-d-galactopyranoside] and its Congeners
  作者：Yingxia Li、Biao Yu、Yichun Zhang、Tiantian Guo、Huashi Guan、Yan Hao

  DOI：10.1055/s-2006-926316

  日期：——

  (25R)-5a-Spirostan-2a,3b-diol (gitogenin) 3β-O-[2-O-(α-l-rhamnopyranosyl)-β-d-galactopyranoside] (1), a cytotoxic spirostan saponin isolated from the underground parts of Hosta longipes (Liliaceae), was concisely synthesized. In this context, its congeners 2-4 were also prepared. All four compounds showed comparable potency to dioscin in inhibition against the growth of tumor cells.

  (25R)-5a-螺甾-2a,3b-二醇 (gitogenin) 3β-O-[2-O-(α-l-鼠李吡喃糖基)-β-d-半乳吡喃糖苷] (1)，一种从长茎黄精（百合科）地下部分分离得到的细胞毒性螺甾皂苷，被简明地合成出来。在此过程中，其类似物2-4也被制备出来。所有四个化合物在抑制癌细胞生长方面与薯蓣皂苷具有相当的效力。
• Synthesis and structure–activity relationship study of cytotoxic germanicane- and lupane-type 3β-O-monodesmosidic saponins starting from betulin
  作者：Dominic Thibeault、Charles Gauthier、Jean Legault、Jimmy Bouchard、Philippe Dufour、André Pichette

  DOI：10.1016/j.bmc.2007.06.033

  日期：2007.9

  triterpenes betulin (1) and betulinic acid (2), respectively. The medical uses of betulinic acid (2) and its derivatives are limited because of their poor hydrosolubility and pharmacokinetics properties. In order to overcome this major problem, we synthesized and studied the in vitro anticancer activity of a series of 3beta-O-monodesmosidic saponins derived from betulin (14-16), betulinic acid (20-22)

  可以通过Wagner-Meerwein重排分别获得更广泛的丁烷型三萜白桦蛋白（1）和桦木酸（2）来获得锗烷型三萜烯别白蛋白（3）和28-氧脂球蛋白（4）。桦木酸（2）及其衍生物的医学用途因其水溶性差和药代动力学特性差而受到限制。为了克服这个主要问题，我们合成并研究了一系列由桦木素（14-16），桦木酸（20-22），同素白蛋白（23-28）衍生的3β-O-单去糖苷皂苷的体外抗癌活性。以及基于六个不同天然糖残基（d-葡萄糖，l-鼠李糖，d-阿拉伯糖，d-半乳糖，d-甘露糖和d-木糖）的28-氧脂球蛋白（29-34）。这项结构与活性之间的关系研究证实，桦木酸皂苷通常比衍生自桦木素的体外抗癌药更好，但桦木素3β-O-α-d-甘露吡喃糖苷除外（15），对肺癌具有有效的细胞毒性作用（ A-549）和大肠腺癌（DLD-1）人细胞系，IC（50）范围为7.3至10.1μmol/ L。此外，尽管成功合成了