2'-azidoethyl-2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside | 882873-74-7

• 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'-azidoethyl-2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside
• 英文别名: (2-Azidoethyl)-2,3,4,6-tetra-O-acetyl-alpha-D-galactopyranoside；[(2R,3S,4S,5R,6S)-3,4,5-triacetyloxy-6-(2-azidoethoxy)oxan-2-yl]methyl acetate
• CAS: 882873-74-7
• 化学式: C₁₆H₂₃N₃O₁₀
• 分子量: 417.373
• InChiKey: DPAXDKFCBLGMIZ-CWVYHPPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  29
• 可旋转键数：
  13
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  138
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  2'-azidoethyl-2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 2-azidoethyl α-D-galactopyranoside
  参考文献：
  名称：

  Carbohydrate Microarrays for Assaying Galactosyltransferase Activity

  摘要：

  Carbohydrate microarrays have been used recently for the rapid analysis of glycan-protein or glycan-cell interactions and for the detection of pathogens. As a demonstration of its significance and versatility, the microarray technology has been applied in this effort to assay glycosyltransferase activities. In addition, carbohydrate microarray based methods have been employed to quantitatively determine binding affinities between lectins and carbohydrates.

  DOI：

  10.1021/ol070250l
• 作为产物：
  描述：

  1-O-(2,3,4,6-tetraacetyl-D-galactoside)-2-bromoethane 在 甲醇 、 sodium azide 、 硫酸 、 silica gel 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 生成 2'-azidoethyl-2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside
  参考文献：
  名称：

  异多价糖基寡聚体作为血型抗原的模拟物

  摘要：

  通过在高度定义的合成支架上显示多个聚糖表位，精密糖大分子已被证明是研究多价碳水化合物-凝集素相互作用的重要工具。在本文中，我们提出了一种新的策略，用于杂合多价糖大分子的多功能组装，该杂多价糖大分子在侧链内附近包含不同的碳水化合物基序。开发了一种适用于精密糖大分子固相聚合物合成的新构件，其侧链上的支化点带有一个游离炔和一个TIPS保护的炔部分，这使得随后的不同碳水化合物基序可以通过on-树脂铜介导的叠氮化物-炔烃环加成反应。应用这种综合策略，

  DOI：

  10.1002/chem.201804505

文献信息

• A One-Step Synthesis of Azide-Tagged Carbohydrates: Versatile ­Intermediates for Glycotechnology
  作者：Lara Mahal、Aditya Sanki

  DOI：10.1055/s-2006-926264

  日期：——

  Herein we describe a simple and practical methodology for accessing both the α-anomers (d-mannose, N-acetyl-d-glucosamine, N-acetyl-d-galactosamine, d-lactose) and α- and β-anomers (d-glucose, d-galactose, l-fucose) of 2′-azidoethyl and azidotriethylene glycol glycosides using free sugars and Dowex 50 (resin) as an efficient catalyst. These azidoalkyl glycosides are increasingly useful synthetic intermediates for glycotechnology.

  本文描述了一种简单实用的方法，能够获取2′-氮杂乙基和氮杂三乙烯二醇糖苷的α-异构体（d-甘露糖、N-乙酰-d-葡萄糖胺、N-乙酰-d-半乳糖胺、d-乳糖）以及α-和β-异构体（d-葡萄糖、d-半乳糖、l-岩藻糖），采用游离糖和Dowex 50（树脂）作为高效催化剂。这些氮杂烷基糖苷在糖科技中越来越成为有用的合成中间体。
• GLYCOSIDE DERIVATIVES, PREPARATION THEREOF AND USE THEREOF AS PROSTHETIC GROUPS
  申请人：UNIVERSITÉ DE LORRAINE

  公开号：US20160031923A1

  公开（公告）日：2016-02-04

  The present invention relates to glycoside-derived compounds, to the processes for preparing same and to the use thereof as prosthetic groups for radiolabelling biomolecules. These compounds are co-azido-alkyl 6-deoxy-6-[ 18 F]-fluoroglycosides of formula (I), in which: k is equal to 2 or 3; n is an integer between 1 and 5; R is independently H or a C 1 -C 5 alkyl group, m being an integer between 0 and 2 if k=2 and m between 0 and 3 if k=3; and X is chosen from the group comprising O, S, CH 2 and NR′, in which R′ is independently a C 1 -C 5 alkyl group or an aryl group, including all the stereoisomers thereof.

  本发明涉及糖苷衍生化合物，制备这些化合物的方法以及将其用作放射标记生物分子的假体基团。这些化合物是公式（I）的共氮烷基6-去氧-6-[18F]-氟糖苷，其中：k等于2或3；n是1到5之间的整数；R独立地是H或C1-C5烷基，如果k=2，则m是0到2之间的整数，如果k=3，则m是0到3之间的整数；X从包括O、S、CH2和NR′的群体中选择，其中R′独立地是C1-C5烷基或芳基，包括所有的立体异构体。
• Preparation of dendritic carboranyl glycoconjugates as potential anticancer therapeutics
  作者：Biswa Ranjan Swain、Chandra Sekhara Mahanta、Bibhuti Bhusan Jena、Swaraj Kumar Beriha、Bismita Nayak、Rashmirekha Satapathy、Barada P. Dash

  DOI：10.1039/d0ra07264h

  日期：——

  o-Carborane-appended glycoconjugates containing multiple glucose and galactose moieties are found to be more cytotoxic towards cancer cells than normal cells.

  含有多个葡萄糖和半乳糖基团的o-碳硼烷缀合的糖缀合物被发现对癌细胞的细胞毒性比对正常细胞更高。

• GLYCOMIMETIC COMPOUNDS AS ANTI-INFECTIOUS AGAINST PATHOGENS LECTINS
  申请人：Imberty Anne

  公开号：US20130252910A1

  公开（公告）日：2013-09-26

  The present invention relates to a calixarene-based glycosylated compound (I) having the formula: (I) wherein D is independently selected in the group comprising a —CH 2 -group, an oxygen atom, a sulphur atom, a sulfinyl group or a sulfonyl group, E is independently selected in the group comprising a hydrogen, an alkyl having from 1 to 10 carbon atoms, an aryl having from 6 to 20 carbon atoms, a nitrogen dioxide group, an azide group, an amino group, a guanidinium group, a halogen atom, a —CH 2 R group wherein R is a hydroxyl, a halogen, an amino group, a N(alkyl) 2 group, a NH(alkyl) group, or E represents a —CO—R′ wherein R′ is a hydrogen atom, a hydroxyl group or an amino, B represents a A-C group wherein A is independently selected in the group comprising an oxygen atom, a sulfur atom, a NH group or a (CH 2 ) i group, i being an integer from 1 to 10, C is independently selected in the group comprising a hydrogen, an alkyl, an alkenyl, an alkynyl, or C is a group of formula (II). The present invention also relates to a pharmaceutical composition characterized in that it comprises the said calixarene-based glycosylated compound (I), in combination with pharmaceutically acceptable carriers or diluents. The present invention also relates to the use of the said calixarene-based glycosylated compound (I) or the said pharmaceutical composition, for the manufacture of a drug intended to prevent or treat bacterial infections from pathogens that use lectins in the first steps of infection.

  本发明涉及一种基于杯芳烃的糖基化化合物（I），其化学式如下：（I）其中D在以下组中独立选择：—CH2基团、氧原子、硫原子、亚砜基或磺酰基；E在以下组中独立选择：氢、具有1至10个碳原子的烷基、具有6至20个碳原子的芳基、亚硝基团、叠氮基团、氨基、胍胺基、卤原子、— R基团（其中R是羟基、卤原子、氨基、N（烷基）2基团、NH（烷基）基团）或E代表—CO—R'（其中R'是氢原子、羟基或氨基），B代表A-C基团（其中A在以下组中独立选择：氧原子、硫原子、NH基团或（ ）i基团，i为1至10的整数），C在以下组中独立选择：氢、烷基、烯基、炔基，或C是化学式（II）的基团。本发明还涉及一种药物组合物，其特征在于它包括所述的基于杯芳烃的糖基化化合物（I），与药学上可接受的载体或稀释剂结合。本发明还涉及所述的基于杯芳烃的糖基化化合物（I）或所述的药物组合物的用途，用于制造用于预防或治疗利用凝集素进行感染起始阶段的病原体引起的细菌感染的药物。
• A convenient approach for solution-phase synthesis of water-soluble galactoside libraries
  作者：Feng Hong、Erkang Fan

  DOI：10.1016/s0040-4039(01)01180-7

  日期：2001.8

  A convenient approach for the solution-phase synthesis of water-soluble galactoside libraries through tributylphosphine promoted reaction of azido compounds with carboxylic acids is described.

  描述了一种通过三丁基膦促进叠氮基化合物与羧酸的反应液相合成水溶性半乳糖苷文库的简便方法。