5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-1-(methoxycarbonyl)-D-glycero-α-D-galacto-2-nonulopyranosyl diethyl phosphite | 145240-79-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-1-(methoxycarbonyl)-D-glycero-α-D-galacto-2-nonulopyranosyl diethyl phosphite
• 英文别名: 4,5,7,8,9-pentaacetyl-2-(diethylphospho)-β-neuraminic acid methyl ester；1-O-diethylphosphite-4,7,8,9-tetra-O-acetyl-N-acetylneuraminic acid methyl ester；methyl (2R,4S,5R,6R)-5-acetamido-4-acetyloxy-2-diethoxyphosphanyloxy-6-[(1S,2R)-1,2,3-triacetyloxypropyl]oxane-2-carboxylate
• CAS: 145240-79-5
• 化学式: C₂₄H₃₈NO₁₅P
• 分子量: 611.537
• InChiKey: AMYUXHLIZHHOQZ-KZXFCMPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  41
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  198
• 氢给体数：
  1
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-1-(methoxycarbonyl)-D-glycero-α-D-galacto-2-nonulopyranosyl diethyl phosphite 在 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 sodium methylate 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Investigation of the Stability of Thiosialosides toward Hydrolysis by Sialidases Using NMR Spectroscopy

  摘要：

  H-1 NMR spectroscopy has been used to investigate whether the alpha(2-->6)-linked thiosialoside 3 and the alpha(2-->3)-linked thiosialoside 9 are hydrolyzed in the presence of Vibrio cholerae sialidase, Similarly, the hydrolysis of the O-ketosides Neu5Ac-2-O-alpha-(2-->3)-Gal beta Me (4) and the alpha-(2-->6)-sialyllactoside 7, representing natural alpha(2-->3)- and alpha(2-->6)-linked sialosides, respectively, was investigated. The results of the H-1 NMR experiments clearly demonstrate that the thiosialosides are not hydrolyzed by Vibrio cholerae sialidase, As expected, the O-sialosides are hydrolyzed to give N-acetyl-alpha-D-neuraminic acid as the first product of substrate cleavage.

  DOI：

  10.1021/ol990652w
• 作为产物：
  描述：

  N-乙酰神经氨酸甲酯 生成 5-acetamido-4,7,8,9-tetra-O-acetyl-3,5-dideoxy-1-(methoxycarbonyl)-D-glycero-α-D-galacto-2-nonulopyranosyl diethyl phosphite
  参考文献：
  名称：

  神经节苷脂GM3的全合成。

  摘要：

  审查了神经节苷脂GM3（NeuAc alpha3Gal beta4Glc beta1Cer）的先前合成，并研究了化学酶和化学全合成方法。在化学酶学方法中，（2S，3R，4E）-5'''-乙酰基-α-神经氨酸-（2'''-> 3''）-β-吡喃半乳糖基-（1''-> 4'使用重组β-Gal-（1''-> 3'可以轻松制备）-β-吡喃葡萄糖基-（1'-> 1）-2-叠氮基-4-十八碳烯1，，3-二醇（azidoGM3） / 4'）-GlcNAcα-（2'''-> 3''）-唾液酸转移酶，被评估为神经节苷脂GM3的合成中间体。神经节苷脂GM3的化学全合成以迄今报道的最大规模之一进行。该合成的亮点包括最小化制备作为有用的异头混合物的乳糖基受体所必需的步骤，对于与已知神经氨酰基供体的高度区域选择性和相当立体选择性的唾液酸化，过量存在以得到被保护的GM3三糖。合成方法通过充分表征的GM3三糖三氯乙亚氨

  DOI：

  10.1016/s0008-6215(00)00121-x

文献信息

• Microbial Glycosyltransferases for Carbohydrate Synthesis:  α-2,3-Sialyltransferase from <i>Neisseria </i><i>g</i><i>onorrheae</i>
  作者：Masayuki Izumi、Gwo-Jenn Shen、Shirley Wacowich-Sgarbi、Takuji Nakatani、Oliver Plettenburg、Chi-Huey Wong

  DOI：10.1021/ja011382r

  日期：2001.11.1

  exploitation of its substrate specificity and synthetic utility. Several potential acceptor substrates were synthesized in this study, including mono- and oligosaccharides, glycolipids, and glycopeptides and their sulfate derivatives. Some CMP-sialic acid derivatives with modification at the C-5 position were also prepared for evaluation as donor substrates. It was found that the enzyme exhibits a broader

  来自淋病奈瑟菌的 α-2,3-唾液酸转移酶在大肠杆菌中过度生产，以利用其底物特异性和合成效用。本研究合成了几种潜在的受体底物，包括单糖和寡糖、糖脂、糖肽及其硫酸盐衍生物。还制备了一些在 C-5 位进行修饰的 CMP-唾液酸衍生物作为供体底物进行评估。发现与其他唾液酸转移酶相比，该酶表现出更广泛的受体底物特异性，尽管供体特异性非常有限。已证明该酶在代表性唾液酸糖缀合物的制备性合成中的应用。在这项工作和其他人的工作的基础上，
• O-Glycosyl Amino Acids by 2-Nitrogalactal Concatenation − Synthesis of a Mucin-Type O-Glycan
  作者：Gottfried A. Winterfeld、Ahmed I. Khodair、Richard R. Schmidt

  DOI：10.1002/ejoc.200390142

  日期：2003.3

  N-Fmoc-protected serine and threonine esters to 2-nitrogalactal derivatives 2 and 26 led highly selectively to α-glycosides 4a−d and 27a,c, respectively. Ensuing transformation of threonine derivative 4d and serine derivatives 4a,b resulted in compounds useful as lysine and dipeptide mimetics. 6-O-Desilylation of 27a,c, then 6-O-sialylation, and transformation of the nitro group of the galactose moiety into a 2-acetamido

  N-Boc 和 N-Fmoc 保护的丝氨酸和苏氨酸酯的碱基促进迈克尔型加成到 2-硝基半乳糖衍生物 2 和 26 分别导致高度选择性地生成 α-糖苷 4a-d 和 27a,c。随后苏氨酸衍生物4d和丝氨酸衍生物4a、b的转化产生用作赖氨酸和二肽模拟物的化合物。27a,c 的 6-O-脱甲硅烷基化，然后 6-O-唾液酸化，并将半乳糖部分的硝基转化为 2-乙酰氨基官能团，得到 N-Boc 保护的丝氨酸和苏氨酸叔丁酯 31a,c在羟基上携带 O 保护的 STN 抗原。然后将苏氨酸衍生物 31c 转化为 N-Fmoc 保护的氨基酸结构单元 33，其用于合成粘蛋白重复单元部分结构 Ac-GS(STN)-TAPPAHG-NH2 (1)。
• Synthesis of oligosaccharides structurally related to E-selection ligands
  作者：Kamaljit Singh、Alfonso Fernández-Mayoralas、Manuel Martín-Lomas

  DOI：10.1039/c39940000775

  日期：——

  A tri- and a tetra-saccharide derived from methyl 3-fucosyl-β-lactoside with sulfate and N-acetylneuraminyl groups at the C-3 position of the galactose unit, analogues of sulfated Lewis X trisaccharide and sialyl Lewis X respectively, have been efficiently prepared from methyl β-lactoside in short syntheses.

  从甲基3-富果糖-β-乳糖苷衍生的三糖和四糖，分别在半乳糖单元的C-3位置引入硫酸盐和N-乙酰神经氨酸基团，其结构类似于硫酸化的Lewis X三糖和唾液酸Lewis X，已通过短时间合成有效地从甲基β-乳糖苷中制备。
• βGal(1–3)GalNAc block donor for the synthesis of TF and α Sialy(2–6)TF as glycopeptide building blocks
  作者：Dongxu Qiu、Sham S. Gandhi、R.Rao Koganty

  DOI：10.1016/0040-4039(95)02229-5

  日期：1996.1

  with peracetylated galactose is found to be an excellent donor for the synthesis of Thomsen-Freidenreich (TF) family of antigens. These may serve further as building blocks for the synthesis of mucin derived glycopeptides and as intermediates for further extention to trisaccharides such as sialyl-TF and 6-O-βGlcNAc-TF(core 2). TF and Sialylated TF are widely regarded as tumor associated and are being

  发现在3位用过乙酰化的半乳糖保护的4,6-苄叉基保护的N-乙酰半乳糖胺β-糖基化是合成Thomsen-Freidenreich（TF）家族抗原的极好供体。这些可以进一步用作合成粘蛋白衍生的糖肽的基础，并用作进一步延伸至三糖如唾液酸-TF和6-O-βGlcNAc-TF（核心2）的中间体。TF和唾液酸化的TF被广泛认为是与肿瘤相关的，并且正在被研究作为抗原用于上皮来源的癌症的免疫治疗。
• Synthesis of N-modified ganglioside GM3 derivatives
  作者：Mingwei Zheng、Xin-Shan Ye

  DOI：10.1016/j.tet.2011.12.019

  日期：2012.2

  Ganglioside GM3 and its derivatives have many important biological functions. Using diethyl phosphite protected sialic acid as glycosyl donor and 3,2′,3′,4′-unprotected lactose as glycosyl acceptor, the sialic acid-containing trisaccharide was assembled with excellent anomeric stereoselectivity. The trisaccharide was further coupled with ceramide precursor to yield sphingosine 1. Based on this key

  神经节苷脂GM3及其衍生物具有许多重要的生物学功能。使用亚磷酸二乙酯保护的唾液酸作为糖基供体，并用3,2'，3'，4'-未保护的乳糖作为糖基受体，以优异的异头立体选择性组装了含唾液酸的三糖。将该三糖进一步与神经酰胺前体偶联以产生鞘氨醇1。基于该关键中间体，顺利合成了唾液酸残基的氮或神经酰胺部分的氮具有修饰的两个不同系列的N-修饰的GM3类似物和GM3本身。