3,4-di-O-acetyl-D-fucal | 75829-69-5

• 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: 3,4-di-O-acetyl-D-fucal
• 英文别名: 3,4-di-O-acetyl-1,5-anhydro-2,6-dideoxy-D-lyxo-hex-1-enitol；di-O-acetyl-6-deoxy-d-galactal；[(2R,3S,4R)-3-acetyloxy-2-methyl-3,4-dihydro-2H-pyran-4-yl] acetate
• CAS: 75829-69-5
• 化学式: C₁₀H₁₄O₅
• 分子量: 214.218
• InChiKey: NDEGMKQAZZBNBB-DRTBCBBWSA-N

物化性质

• 沸点：
  295.9±0.0 °C(Predicted)
• 密度：
  1.16±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3,4-di-O-acetyl-D-fucal 在 sodium methylate 、 二正丁基氧化锡 、 cesium fluoride 作用下， 以 甲醇 为溶剂， 反应 16.0h， 生成 1,5-anhydro-2,6-dideoxy-3-O-<(4-methoxyphenyl)methyl>-D-lyxo-hex-1-enopyranoside
  参考文献：
  名称：

  Studies Related to the Carbohydrate Sectors of Esperamicin and Calicheamicin: Definition of the Stability Limits of the Esperamicin Domain and Fashioning of a Glycosyl Donor from the Calicheamicin Domain

  摘要：

  The core trisaccharide regions of esperamicin and the aryltetrasaccharide region of calicheamicin have been synthesized. The minimum protection modalities necessary to stabilize structures against rearrangement to an isomeric azafuranose series were ascertained (see compounds 12 and 65). Deprotection of the 2-(trimethylsilyl)ethoxycarbonyl carbamate from 65 led to azafuranose 14 characterized as methyl glycoside 15. Using this insight, it was possible to fashion, for the first time, a pre-glycosyl donor (see compound 128) corresponding to the complete arylsaccharide sector of calicheamicin gamma(1)(I) at the oxidation level of the domain. Among the key assembly strategies were the conversion of alpha-thiophenylpseudoglycals to allal derivatives (see 44 --> 45); the interfacing of epoxide-mediated glycosylation with iodoglycosylation (see 30 --> 47 --> 48); the synthesis of hydroxylamine glycosides via triflate displacement (see 61 + 91 --> 101); and a new route to p-hydroxybenzonitriles (see formation of 86).

  DOI：

  10.1021/ja00126a013
• 作为产物：
  描述：

  2,3,4-tri-O-acetyl-D-fucopyranosyl bromide 在 N-甲基咪唑 、 锌 作用下， 以 乙酸乙酯 为溶剂， 以70%的产率得到3,4-di-O-acetyl-D-fucal
  参考文献：
  名称：

  摘要：

  In connection with studies on the biosynthesis of capsular polysaccharides from Staphylococcus aureus, a new synthesis of uridine 5'-(2-acetamido-2,6-dideoxy-alpha-D-galactopyranosyl diphosphate) (uridine 5'-diphospho-N-acetyl-alpha-D-fucosamine) using 2-azido-3,4-di-O-acetyl-2,6-dideoxy-alpha-D-galactopyranosyl nitrate as the key intermediate was carried out. The reaction of this product with cesium dibenzyl phosphate smoothly affords the corresponding beta-glycosyl dibenzyl phosphate, which undergoes anomerization on treatment with BF(3).Et(2)O and 2-bromopyridine to give alpha-glycosyl dibenzyl phosphate in high yield. This product was then transformed into 2-amino-3,4-di-O-acetyl-2,6-dideoxy-alpha-D-galactopyranosyl phosphate, subsequently converted into 2-acetamido-2,6-dideoxy-alpha-D-galactopyranosyl phosphate and the target nucleoside diphosphate sugar.

  DOI：

  10.1023/a:1014035613269

文献信息

• Synthesis of the Common Monomeric Unit of Uroleuconaphins and Viridaphins via Hauser–Kraus Annulation
  作者：Kei Kitamura、Hiroto Kaku、Hinano Kanagawa、Chiharu Ozakai、Taichi Nishimura、Hayato Tokuda、Tetsuto Tsunoda

  DOI：10.1055/a-1334-6982

  日期：2021.5

  A stereoselective synthesis of a pyranonaphthoquinone derivative found in aromatic polyketide-derived aphid pigments is reported herein. This approach features the anionic [4+2]-annulation of phthalides with a carbohydrate-derived optically active enone. Additional synthetic steps provide access to the monomer fragment of uroleuconaphins and viridaphins. The optimization for a facile preparation of

  本文报道了在芳族聚酮化合物衍生的蚜虫颜料中发现的吡喃并萘醌衍生物的立体选择性合成。该方法的特征是邻苯二甲酸酯与碳水化合物衍生的旋光性烯酮的阴离子[4 + 2]环化。额外的合成步骤提供了接近尿亮豆球蛋白和维达啡的单体片段的途径。还研究了简便制备带有磺酰基或氰基的邻苯二甲酸酯的优化方法。
• 3-Aminodeoxypyranoses in Glycosylation: Diversity-Oriented Synthesis and Assembly in Oligosaccharides
  作者：Jing Zeng、Guangfei Sun、Wang Yao、Yangbin Zhu、Ruobin Wang、Lei Cai、Ke Liu、Qian Zhang、Xue-Wei Liu、Qian Wan

  DOI：10.1002/anie.201700178

  日期：2017.5.2

  concise, diversity‐oriented approach for the synthesis of naturally occurring 3‐amino‐ and 3‐nitro‐2,3,6‐trideoxypyranose derivatives and analogues thereof from simple sugars has been developed. In addition, we investigated the synthesis of various 3‐aminoglycosyl donors and their application in glycosylation reactions. These studies led to the successful synthesis of a tetrasaccharide containing four different

  已开发出一种简洁，面向多样性的方法，可从简单糖中合成天然存在的3-氨基和3-硝基2,3,6-三苯氧基吡喃糖衍生物及其类似物。此外，我们研究了各种3-氨基糖基供体的合成及其在糖基化反应中的应用。这些研究导致使用邻炔基苯甲酸酯供体成功合成了包含四种不同的3-氨基糖组分的四糖。
• Environmentally compatible C-glycosidation of glycals using montmorillonite K-10
  作者：Kazunobu Toshima、Naoki Miyamoto、Goh Matsuo、Masaya Nakata、Shuichi Matsumura

  DOI：10.1039/cc9960001379

  日期：——

  The C-glycosidations of glycal acetates 1–4 with allyltrimethylsilane 5, vinyloxytrimethylsilane 6 or isopropenyl acetate 7 using montmorillonite K-10 as an environmentally acceptable and inexpensive industrial catalyst under mild conditions proceed effectively to give the corresponding 2,3-unsaturated C-glycosides in high yields.

  甘油醛乙酸酯1-4在温和条件下，以蒙脱土K-10作为环境友好且经济的工业催化剂，与烯丙基三甲基硅烷5、乙烯氧基三甲基硅烷6或异丙烯基乙酸酯7进行C-糖基化反应，高效地生成了相应的2,3-不饱和C-糖苷，产率极高。
• Hydrogen-Bonding-Assisted Exogenous Nucleophilic Reagent Effect for β-Selective Glycosylation of Rare 3-Amino Sugars
  作者：Jing Zeng、Ruobin Wang、Shuxin Zhang、Jing Fang、Shanshan Liu、Guangfei Sun、Bingbing Xu、Ying Xiao、Dengxian Fu、Wenqi Zhang、Yixin Hu、Qian Wan

  DOI：10.1021/jacs.9b01862

  日期：2019.5.29

  Challenges for stereoselective glycosylation of deoxy sugars are notorious in carbohydrate chemistry. We herein report a novel strategy for the construction of the less investigated β-glycosidic bonds of 3,5- trans-3-amino-2,3,6-trideoxy sugars (3,5- trans-3-ADSs), which constitute the core structure of several biologically important antibiotics. Current protocol leverages a C-3 axial sulfonamide group

  脱氧糖的立体选择性糖基化挑战在碳水化合物化学中是众所周知的。我们在此报告了一种构建较少研究的 3,5-反式-3-氨基-2,3,6-三脱氧糖（3,5-反式-3-ADS）的β-糖苷键的新策略，其构成几种生物学上重要的抗生素的核心结构。当前协议利用 3,5-trans-3-ADS 中的 C-3 轴向磺酰胺基团作为氢键（H 键）供体，并将亚化学计量氧化膦重新用作外源亲核试剂（exNu）以建立分子内 H-前者和衍生的α-氧鏻离子之间的键。这种关键的相互作用稳定了 α-面覆盖的中间体，以抑制更具反应性的 β-中间体的形成，从而产生反向的 β-选择性，这对于 exNu 介导的糖基化系统来说是非常规的。适应了广泛的底物，并且通过这种 H 键辅助的 exNu 效应确保了良好到出色的 β 选择性。当前策略的稳健性通过天然产物和含有 3,5-反式-3-ADS 的药物的结构修改以及抗生物素蛋白红素中三糖单元的合成得到进一步证明。
• Synthesis of orthogonally protected and functionalized bacillosamines
  作者：Jeanine van Mechelen、Jim Voorneveld、Hermen S. Overkleeft、Dmitri V. Filippov、Gijsbert A. van der Marel、Jeroen D. C. Codée

  DOI：10.1039/d0ob00256a

  日期：——

  2,4-Diamino-2,4,6-trideoxyglucose (bacillosamine) is a monosaccharide found in many pathogenic bacteria, variation in the functionalities appended to the amino groups occurs depending on the species the sugar is derived from. We here report the first synthesis of bacillosamine synthons that allow for the incorporation of two different functionalities at the C-2-N-acetyl and C-4-amines. We have developed

  2,4-二氨基-2,4,6-三脱氧葡萄糖（bacillosamine）是在许多致病细菌中发现的单糖，取决于糖的来源种类，氨基上附加的官能团会发生变化。我们在这里报道了杆菌胺合成子的首次合成，其允许在C-2- N-乙酰基和C-4-胺上引入两种不同的功能。我们已经开发出化学方法来组装一套易于结合的脑膜炎奈瑟氏球菌C-2- N-乙酰基杆菌胺糖，在C-4胺上带有乙酰基或（R）-或（S）-甘油酰。甘油酰杆菌胺已在C-3-OH处用α- D进一步延伸-半乳糖吡喃糖提供的结构是脑膜炎奈瑟氏菌PilE蛋白的翻译后修饰，构成细菌菌毛。