4,8-anhydro-1,3-dideoxy-D-glycero-L-gluco-nonulose | 469873-52-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4,8-anhydro-1,3-dideoxy-D-glycero-L-gluco-nonulose
• 英文别名: 1-((2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)propan-2-one；1-[(2S,3R,4R,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]propan-2-one
• CAS: 469873-52-7
• 化学式: C₉H₁₆O₆
• 分子量: 220.222
• InChiKey: XMNOVTHWCLGVID-QKAWAISNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4,8-anhydro-1,3-dideoxy-D-glycero-L-gluco-nonulose 在 potassium tert-butylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 18.92h， 生成 2-(1-C-β-D-galactopyranosylmethyl)propene
  参考文献：
  名称：

  Multigram Synthesis of Isobutyl-β-C-galactoside as a Substitute of Isopropylthiogalactoside for Exogenous Gene Induction in Mammalian Cells

  摘要：

  Herein we report that isobutyl-beta-C-galactoside (IBCG) is also a promising inducer of gene expression in mammalian cells and report a new synthetic route to the compound that should make obtaining the multigram quantities of material required for animal studies more feasible. A convenient synthesis of IBCG, an inducer of genes controlled by the lac operon system in bacterial cells, was achieved in 5 steps from galactose in 81% overall yield without any chromatographic separation steps. An optimized microwave-assisted reaction at high concentration was key to making the C-glycosidic linkage. A Wittig reaction on a per-O-silylated rather than per-O-acetylated or -benzylated substrate proved most effective in installing the final carbon atom.

  DOI：

  10.1021/jo2024569
• 作为产物：
  描述：

  5,6,7,9-tetra-O-acetyl-4,8-anhydro-1,3-dideoxy-D-glycero-L-gluco-nonulose 在 甲醇 、 sodium methylate 作用下， 以100%的产率得到4,8-anhydro-1,3-dideoxy-D-glycero-L-gluco-nonulose
  参考文献：
  名称：

  Synthesis of stable and selective inhibitors of human galectins-1 and -3

  摘要：

  The syntheses of glycolytically stable galactosides and lactosides have been made toward the selective inhibition of human galectins-1 and -3. Transition metal-catalyzed cross-coupling reactions were used to create carbon-carbon bond formation (Sonogashira, Suzuki, Heck, Glaser). Additionally, Hantzsch condensation was used to create novel 2-aminothiazoles which reacted with a panel of acylating and sulfonylating reagents. Moreover, dimeric galactosides and lactosides bearing triazoles, regiospeci.cally prepared using copper-catalyzed Huisgen azide-alkyne [1,3]-dipolar cycloaddition, provided efficient galectins-1 and -3 inhibitors. Best monovalent inhibitor among the tested series was (E)-methyl 2-phenyl-4-(beta-D-galactopyranosyl)-but-2-enoate 15 with inhibitory potency of 313 mu M against galectin-1 and best dimers were bis-lactoside 68 and 75 having both inhibitory properties of 160 mu M against Galectin-3. (c) 2008 Elsevier Ltd. All rights reserved..

  DOI：

  10.1016/j.bmc.2008.06.044

文献信息

• [EN] GLYCOLIPIDS AND PHARMACEUTICAL COMPOSITIONS THEREOF FOR USE IN THERAPY<br/>[FR] GLYCOLIPIDES ET LEURS COMPOSITIONS PHARMACEUTIQUES DESTINÉES À ÊTRE UTILISÉES EN THÉRAPIE
  申请人：UNIV NOTTINGHAM

  公开号：WO2015150839A1

  公开（公告）日：2015-10-08

  A compound of Formula I: R1 -L1 -C(A)(A') - CH2, - L2-R2 or a pharmaceutically acceptable salt thereof, for use in medicine, for example in the treatment of a disease or condition selected from the group comprising cancer, autistic spectrum disorders. Alzheimer' s disease, Parkinson's disease, Huntingdon' s disease, muscie wasting and viral infection, wherein: R1 is selected from a carbohydrate group or derivative thereof, hydrogen, a C1-C24 alkyl or a C1-C24 derivative of an alkyl group, a C2-C24 alkenyl or a C2-C24 derivative of an aikenyl group, and a C2-C24 alkynyl group or a C2-C24 derivative of an alkynyl group; L1 is a linking group; L2 is a linking group; R2 is selected from hydrogen, a C1-C24 alkyl or a C1-C24 derivative of an alkyl group, a C2-C24 alkenyl or a C2-C24 derivative of an alkenyl group, and a C2-C24 alkynyl group or a C2-C24 derivative of an alkynyl group; A is selected from hydrogen and a C1 -C6 alkyl group: A' is selected from hydrogen, a C3 -C6 alkyl group, and L3-R3; wherein L3 is a linking group; and R3 is selected from hydrogen, a C1-C24 alkyl or a C1-C24 derivative of an alkyl group, a C2-C24 alkenyl or a C2-C24 derivative of an alkenyl group, and a C2-C24 alkynyl group or a C2-C24 derivative of an alkynyl group; and wherein if A' is not L3-R3, then R2 is a C10-C24 alkyl or a C10-C24 derivative of an alkyl group, a C10-C24 alkenyl or a C10-C24 derivative of an alkenyl group, or a C10-C24 alkynyl group or a C10-C24 derivative of an alkynyl group; and wherein if A' is L3-R3, then one or both of R2 and R3 are a C10-C24 alkyl or a C10-C24 derivative of an alkyl group, a C10-C24 alkenyl or a C10-C24 derivative of an alkenyl group, or a C10-C24 alkynyl group or a C10-C24 derivative of an alkynyl group.

  一种化合物，其化学式为：R1 -L1 -C(A)(A') - CH2, - L2-R2或其药学上可接受的盐，用于医药领域，例如用于治疗来自包括癌症、自闭症谱系障碍、阿尔茨海默病、帕金森病、亨廷顿病、肌肉萎缩和病毒感染在内的疾病或症状，其中：R1选自碳水化合物基团或其衍生物、氢、C1-C24烷基或C1-C24烷基衍生物、C2-C24烯基或C2-C24烯基衍生物、C2-C24炔基或C2-C24炔基衍生物；L1为连接基团；L2为连接基团；R2选自氢、C1-C24烷基或C1-C24烷基衍生物、C2-C24烯基或C2-C24烯基衍生物、C2-C24炔基或C2-C24炔基衍生物；A选自氢和C1-C6烷基；A'选自氢、C3-C6烷基和L3-R3；其中L3为连接基团；R3选自氢、C1-C24烷基或C1-C24烷基衍生物、C2-C24烯基或C2-C24烯基衍生物、C2-C24炔基或C2-C24炔基衍生物；如果A'不是L3-R3，则R2为C10-C24烷基或C10-C24烷基衍生物、C10-C24烯基或C10-C24烯基衍生物、或C10-C24炔基或C10-C24炔基衍生物；如果A'是L3-R3，则R2和/或R3为C10-C24烷基或C10-C24烷基衍生物、C10-C24烯基或C10-C24烯基衍生物、或C10-C24炔基或C10-C24炔基衍生物。
• Vanillin enones as selective inhibitors of the cancer associated carbonic anhydrase isoforms IX and XII. The out of the active site pocket for the design of selective inhibitors?
  作者：Leonardo E. Riafrecha、Macarena S. Le Pors、Martín J. Lavecchia、Silvia Bua、Claudiu T. Supuran、Pedro A. Colinas

  DOI：10.1080/14756366.2021.1982933

  日期：2021.1.1

  Abstract New C-glycosides and α,β-unsaturated ketones incorporating the 4-hydroxy-3-methoxyphenyl (vanillin) moiety as inhibitors of carbonic anhydrase (CA, EC 4.2.1.1) isoforms have been investigated. The inhibition profile of these compounds is presented against four human CA (hCA) isozymes, comprising hCAs I and II (cytosolic, ubiquitous enzymes) and hCAs IX and XII (tumour associated isozymes)

  摘要 新C已经研究了含有 4-羟基-3-甲氧基苯基（香草醛）部分的β-糖苷和 α,β-不饱和酮作为碳酸酐酶（CA，EC 4.2.1.1）异构体的抑制剂。这些化合物对四种人类 CA (hCA) 同工酶具有抑制作用，包括 hCAs I 和 II（细胞溶质、普遍存在的酶）和 hCAs IX 和 XII（肿瘤相关同工酶）。已经对这些酶的活性位点内的抑制剂进行了对接分析并进行了讨论，表明观察到的选择性可以解释为 CA 活性位点之外的替代口袋，其中一些化合物可能结合。几种衍生物被鉴定为肿瘤相关 hCA IX 和 XII 的选择性抑制剂。
• Acylation of carbohydrates over Al2O3: preparation of partially and fully acylated carbohydrate derivatives and acetylated glycosyl chlorides
  作者：Pallavi Tiwari、Anup Kumar Misra

  DOI：10.1016/j.carres.2005.11.035

  日期：2006.2

  protocol does not require the addition of any base or activator. This methodology has been further extended to the selective acylation of carbohydrate diols and the one-pot preparation of acetylated glycosyl chlorides direct from free reducing sugars. The yields obtained in most of the cases are excellent.

  据报道，使用酰氯和固体支持剂Al2O3对碳水化合物衍生物进行选择性和全O酰化。该协议不需要添加任何碱或活化剂。该方法已经进一步扩展到碳水化合物二醇的选择性酰化和直接从游离还原糖直接制备一锅乙酰化糖基氯的方法。在大多数情况下所获得的产量是极好的。
• Efficient Acetylation of Carbohydrates Promoted by Imidazole
  作者：Pallavi Tiwari、Rishi Kumar、Prakas R. Maulik、Anup Kumar Misra

  DOI：10.1002/ejoc.200500555

  日期：2005.10

  An efficient per-O-acetylation of carbohydrate derivatives and unprotected reducing sugars promoted by imidazole is reported. The reaction conditions have been successfully employed to acetylate carbohydrate derivatives containing acid-susceptible functional groups. In most of the cases the yields obtained were excellent. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)

  据报道，由咪唑促进的碳水化合物衍生物和未受保护的还原糖的有效过-O-乙酰化。该反应条件已成功用于乙酰化含有酸敏感官能团的碳水化合物衍生物。在大多数情况下，获得的产率非常好。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
• Synthesis of Reverse Glycosyl Fluorides and Rare Glycosyl Fluorides Enabled by Radical Decarboxylative Fluorination of Uronic Acids
  作者：Pengwei Chen、Peng Wang、Qing Long、Han Ding、Guoqiang Cheng、Tiantian Li、Ming Li

  DOI：10.1021/acs.orglett.0c03514

  日期：2020.12.4

  for synthesizing reverse glycosyl fluorides is described, relying on silver-promoted decarboxylative fluorination of structurally diverse pentofuran- and hexopyranuronic acids under the mild reaction conditions. The potential applications of the reaction are further demonstrated by converting readily available d-uronic acid derivatives into uncommon d-/l-glycosyl fluorides through a C1-to-C5 switch

  描述了一种有效的合成逆向糖基氟化物的方法，该方法依赖于在温和的反应条件下，银促进结构上多样的戊呋喃和六吡喃葡萄糖醛酸的脱羧氟化作用。该反应的潜在应用通过通过C1-C5转换策略将容易获得的d-糖醛酸衍生物转化为不常见的d - 1-糖苷氟来进一步证明。反应机理是通过5-证实外切-三角函数烯丙基α-的自由基环化d -C葡吡喃糖醛酸通过脱羧氟化触发。