methyl 2-azido-2-deoxy-α-D-mannopyranoside | 223545-38-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl 2-azido-2-deoxy-α-D-mannopyranoside
• 英文别名: (2R,3S,4R,5S,6S)-5-azido-2-(hydroxymethyl)-6-methoxyoxane-3,4-diol
• CAS: 223545-38-8
• 化学式: C₇H₁₃N₃O₅
• 分子量: 219.197
• InChiKey: QYZPIZZUWJKSTF-BIVRFLNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  93.5
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  methyl 2-azido-2-deoxy-α-D-mannopyranoside 在 氢气 作用下， 以 甲醇 为溶剂， 生成 methyl 2-amino-2-deoxy-α-D-mannopyranoside
  参考文献：
  名称：

  使用氨基糖模型量化碳水化合物羟基的电子效应

  摘要：

  合成了具有α-和β-葡萄糖，α-半乳糖或α-甘露糖立体化学的甲基氨基脱氧糖苷，在四个可能的非异头位置中均具有氨基官能团，并通过滴定确定了其p K a值。选择这些模型化合物是因为它们是最常见的糖基受体的氨基衍生物。通过这项研究，有可能评估碳水化合物中每个给定位置的电子密度并进行比较。观察到一些一般趋势：氨基的碱度以6-NH 2 > 3-NH 2 > 2-NH 2 > 4-NH 2的顺序降低。（指的是位置）。当糖环上的一个或多个取代基为轴向时，氨基脱氧糖α的碱性通常会增加。当胺对氧原子为反平面时，碱度降低。这些发现与从糖基化化学和糖的区域选择性保护获得的观察结果一致。

  DOI：

  10.1002/chem.201100020
• 作为产物：
  描述：

  4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 在 吡啶 、 sodium azide 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 methyl 2-azido-2-deoxy-α-D-mannopyranoside
  参考文献：
  名称：

  基于碳水化合物的N-杂环卡宾，用于对映选择性催化†

  摘要：

  报道了从官能化的氨基碳水化合物衍生物多功能合成C 2连接的和C 2对称的基于碳水化合物的咪唑盐。将新型NHC连接到[Rh（COD）Cl] 2上，并在Rh催化的酮的不对称氢化硅烷化中进行了评估，产率高，对映选择性高。

  DOI：

  10.1039/c4ob02056a

文献信息

• Sweet Drugs for Bad Bugs: A Glycomimetic Strategy against the DC-SIGN-Mediated Dissemination of SARS-CoV-2
  作者：Jonathan Cramer、Adem Lakkaichi、Butrint Aliu、Roman P. Jakob、Sebastian Klein、Ivan Cattaneo、Xiaohua Jiang、Said Rabbani、Oliver Schwardt、Gert Zimmer、Matias Ciancaglini、Tiago Abreu Mota、Timm Maier、Beat Ernst

  DOI：10.1021/jacs.1c06778

  日期：2021.10.27

  screening hit yielded a glycomimetic ligand with a more than 100-fold improved binding affinity compared to methyl α-d-mannopyranoside. Analysis of binding thermodynamics revealed an enthalpy-driven improvement of binding affinity that was enabled by hydrophobic interactions with a loop region adjacent to the binding site and displacement of a conserved water molecule. The identified ligand was employed

  C 型凝集素受体 DC-SIGN 是一种在巨噬细胞和树突细胞上表达的模式识别受体。它已被确定为许多病原体的混杂进入受体，包括流行病和大流行病毒，如 SARS-CoV-2、埃博拉病毒和 HIV-1。在最近的 SARS-CoV-2 大流行的背景下，DC-SIGN 介导的病毒传播和先天免疫反应的刺激被认为是严重 COVID-19 发展的潜在因素。因此，抑制病毒与 DC-SIGN 的结合代表了一种有吸引力的宿主导向策略，以减弱先天免疫反应的过度反应并防止疾病的进展。在这项研究中，我们报告了从基于三唑的甘露糖类似物的重点库中发现的一类新的强效糖模拟物 DC-SIGN 拮抗剂。d-吡喃甘露糖苷。结合热力学分析揭示了焓驱动的结合亲和力的提高，这是通过与结合位点相邻的环区域的疏水相互作用和保守水分子的置换来实现的。所标识的配位体用于该能够抑制SARS-CoV的-2刺突糖蛋白结合DC-SIGN表达细胞的多价
• Glycosylation Using 2-Azido-3,4,6-tri-<i>O</i>-benzyl-2-deoxy-D-glucose, -galactose, and -mannose with the Aid of<i>p</i>-Nitrobenzenesulfonyl Chloride–Silver Trifluoromethanesulfonate–Triethylamine System
  作者：Shinkiti Koto、Kazuyasu Asami、Motoko Hirooka、Kazuo Nagura、Mizue Takizawa、Satoko Yamamoto、Nami Okamoto、Mitsuko Sato、Hiromi Tajima、Toyosaku Yoshida、Nobuo Nonaka、Tadaaki Sato、Shonosuke Zen、Kazuo Yago、Fumiya Tomonaga

  DOI：10.1246/bcsj.72.765

  日期：1999.4

  simple synthesis of 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose. Glycosylation using this as well as 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-galactopyranose and -mannopyranose was achieved with the aid of a reagent system consisting of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine, and its modifications. O-(2-Acetamido-2-deoxy-β-D-glucopyranosyl)-(1→4)-O-α-

  本报告描述了 2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose 的简单合成。在由对硝基苯磺酰氯、三氟甲磺酸银组成的试剂系统的帮助下，使用它以及 2-叠氮基-3,4,6-三-O-苄基-2-脱氧-D-吡喃半乳糖和-吡喃甘露糖实现糖基化，和三乙胺，及其变体。O-(2-乙酰氨基-2-脱氧-β-D-吡喃葡萄糖基)-(1→4)-O-α-D-吡喃甘露糖基-(1→4)-α-D-吡喃甘露糖，主要的重复单元合成了大肠杆菌 058 的 O 特异性细胞壁多糖链。
• Towards a Synthetic Glycoconjugate Vaccine Against Neisseria meningitidis A
  作者：Ali Berkin、Bruce Coxon、Vince Pozsgay

  DOI：10.1002/1521-3765(20021004)8:19<4424::aid-chem4424>3.0.co;2-1

  日期：2002.10.4

  Albumin conjugates of synthetic fragments of the capsular polysaccharide of the Gram-negative bacterium Neisseria meningitidis serogroup A were prepared. The fragments include monosaccharides 1 [alpha-D-ManpNAc(1--> 0)-(CH2)(2)NH2] and 2 [6-O-P(O)-(O-)(2)-alpha-D-ManpNAc-(1 --> O)-(CH2)(2)NH2] ,disaccharide 3 [alpha-D-ManpNAc[1-->O-P(O)(O-) --> 6]-alpha-D-ManpNAc(1 --> O)-(CH2)(2)NH2], and trisaccharide 4 [alpha-D-ManpNAc-[1 -->O-P(O)(O-)--> 6]-alpha-D-ManpNAc-[1 -->O-P(O)(O-)--> 6]-alpha-D-ManpNAc-(1 --> O)-(CH2)(2)NH2]. Two monosaccharide blocks were employed as key intermediates. The reduc-ing-end mannose unit featured the NHAc group at C-2, and contained the aminoethyl spacer as the aglycon for the final bioconjugation. The interresidual phosphodiester linkages were fashioned from an anomerically positioned H-phosphonate group in a 2-azido-man-nose building block. The spacer-linked saccharides 1-4 were N-acylated with hepta-4,6-dienoic acid and the resulting conjugated diene-equipped saccharides were subjected to Diels-Alder-type addition with maleimidobutyryl-group functionalized human serum albumin to form covalent conjugates containing up to 26 saccharide haptens per albumin molecule. Complete H-1, C-13, and P-31 NMR assignments for 1-4 are given. Antigenicity of the neoglycoconjugates containing 1-4 was demonstrated by a double immunodiffusion assay which indicated that a fragment as small as a monosaccharide is recognized by a polyclonal meningococcus group A antiserum and that the O-acetyl group(s) present in the natural capsular material is not essential for antigenicity.
• Tandem reduction–reductive alkylation of azido sugars
  作者：Liqiang Chen、David F. Wiemer

  DOI：10.1016/s0040-4039(02)00386-6

  日期：2002.4

  Catalytic hydrogenation of azido sugars has been conducted in the presence of different aldehydes to bring about a tandem reduction-reductive alkylation sequence. The reaction sequence proceeds in generally high yields, and tolerates some benzyl and benzylidene protecting groups that are sensitise to hydrogenolysis. (C) 2002 Elsevier Science Ltd. All rights reserved.
• [EN] CARBOHYDRATE-BASED SCAFFOLD COMPOUNDS, COMBINATORIAL LIBRARIES AND METHODS FOR THEIR CONSTRUCTION<br/>[FR] COMPOSES D'ECHAFAUDAGE A BASE D'HYDRATE DE CARBONE, BANQUES COMBINEES, ET LEURS PROCEDES DE CONSTRUCTION
  申请人：——

  公开号：WO1999061583A2

  公开（公告）日：1999-12-02

  [EN] A compound of structure (I) wherein X is O or S; Z is O or NH; Y is COOH, COOR2, CH2OR3, CH3, or CH(s)Y2(3-s) where Y2 is F, Cl, Br or I, and s is 0, 1, or 2 or Y and one of ZR4 and OR5 are linked to form a 6-membered cyclic acetal; p is O or 1; m is 0 or 1; n is 1 or 2. A library of compounds of structure (II) wherein X is O or S; A1 is a residue of an alpha -amino acid attached through a terminal amino, a peptide residue comprising residues of from 2 to 10 alpha -amino acids and attached through a terminal amino, R1O, R1S, R1, R1NH or R1N-alkyl; A2 is a residue of an alpha -amino acid attached through a terminal carboxyl, a peptide residue comprising residues of from 2 to 10 alpha -amino acids and attached through a terminal carboxyl, R2SO2, R2NHCO, R2OP(O) (OR6), R2P(O) (OR6) or R2, or A2, A3 and N combine to form a nitrogen heterocycle; A3 is hydrogen when A3 is not combined with A2 and N; A4 is OR4, NHR4, CH2OR4 or CH3; A5 is O, NH or N-alkyl; p, q and r are independently 0 or 1; Y1 and Y2 are independently O or CH2; each of L1 and L2 is independently a difunctional alkyl, aryl, aralkyl, alkanoyl, aroyl or aralkanoyl group; L3 is a single bond, CH2, carbonyl, OP(O) (OR7), NHP(O) (OR7), P(O) (OR7) or (III) wherein W is O, NH, N-alkyl or S, and Z is NH, O or S; m is 0 or 1; and n is 1 or 2.
  [FR] L'invention concerne un composé de structure (I), dans laquelle X représente O ou S; Z représente O ou NH; Y représente COOH, COOR2, CH2OR3, CH3, ou CH(s)Y2(3-s), Y2 désignant F, Cl, Br, ou I, et s étant égal à 0, à 1, ou à 2, ou Y, ZR4 ou OR5 sont liés pour former un acétal cyclique à 6 chaînons; p est égal à 0 ou à 1; m est égal à 0 ou à 1; et n est égal à 1 ou à 2. L'invention concerne également une banque de composés de structure (II), dans laquelle X représente O ou S; A1 désigne un reste d'un alpha -aminoacide relié par un amino terminal, un reste peptidique renfermant des restes d'environ 2 à 10 alpha -aminoacides et étant relié par un amino terminal, R1O, R1S, R1, R1NH, ou R1N-alkyle; A2 désigne un reste d'un alpha -aminoacide relié par un carboxyle terminal, un reste peptidique renfermant des restes d'environ 2 à 10 alpha -aminoacides et étant relié par un carboxyle terminal, R2SO2, R2NHCO, R2OP(O) (OR6), R2P(O) (OR6), ou R2, ou A2, A3, et N s'associent pour former un hétérocycle azoté; A3 représente hydrogène quand A3 n'est pas associé à A2 et à N; A4 représente OR4, NHR4, CH2OR4, ou CH3; A5 représente O, NH, ou N-alkyle; p, q, et r sont indépendamment égaux à 0 ou à 1; Y1 et Y2 désignent indépendamment O ou CH2; L1 et L2 représentent chacun un groupe alkyle, aryle, aralkyle, alkanoyle, aroyle, ou aralkanoyle dysfonctionnel; L3 symbolise une liaison simple, CH2, carbonyle, OP(O) (OR7), NHP(O) (OR7), P(O) (OR7), ou (III), dans laquelle W représente O, NH, N-alkyle ou S, et Z désigne NH, O, ou S; m est égal à 0 ou à 1; et n est égal à 1 ou à 2.