5,6,7,9-tetra-O-acetyl-4,8-anhydro-1,3-dideoxy-D-glycero-L-gluco-nonulose | 853269-40-6

• 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: 5,6,7,9-tetra-O-acetyl-4,8-anhydro-1,3-dideoxy-D-glycero-L-gluco-nonulose
• 英文别名: 1-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)propan-2-one；[(2R,3S,4R,5S,6S)-3,4,5-triacetyloxy-6-(2-oxopropyl)oxan-2-yl]methyl acetate
• CAS: 853269-40-6
• 化学式: C₁₇H₂₄O₁₀
• 分子量: 388.372
• InChiKey: DWRNVUXNLZJUGM-BQJWPVKWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  27
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  132
• 氢给体数：
  0
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5,6,7,9-tetra-O-acetyl-4,8-anhydro-1,3-dideoxy-D-glycero-L-gluco-nonulose 在 甲醇 、 sodium 、 4-甲基苯磺酸吡啶 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 、 苯 为溶剂， 反应 11.5h， 生成 1-C-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)propan-2-one ethylene ketal
  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：

  D-吡喃葡萄糖 在 吡啶 、 碳酸氢钠 作用下， 以 水 为溶剂， 生成 5,6,7,9-tetra-O-acetyl-4,8-anhydro-1,3-dideoxy-D-glycero-L-gluco-nonulose
  参考文献：
  名称：

  C-肉桂酰基糖苷的合成及其对哺乳动物碳酸酐酶的抑制活性

  摘要：

  通过使糖基酮与适当的苯甲醛反应，已经制备了少量的结合有酚部分的C-肉桂酰基糖苷。测试了糖苷对十二种碳酸酐酶哺乳动物同工型的抑制作用。这是首次研究α-CA与C-糖苷的相互作用的研究，C-糖苷是碳酸酐酶抑制剂设计中的新型碳水化合物支架。该ç-肉桂酰基糖苷通常是有效的CA抑制剂，对CA I，II，IV，VA，VB，VI，VII，IX，XII，XIII，XIV和无效的CA III抑制剂的抑制常数在低微摩尔范围内。这些结果证实，将碳水化合物部分连接至CA酚药效团改善了其抑制活性。

  DOI：

  10.1016/j.bmc.2012.09.002

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。
• 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)
• Diastereoselective addition of sugar radicals to camphorsultam glyoxilic oxime ether: a route toward C-glycosylthreonine and allothreonine
  作者：Nicolas Bragnier、Regis Guillot、Marie-Christine Scherrmann

  DOI：10.1039/b910050d

  日期：——

  C-glucosyl, mannosyl and galactosyl 2-iodopropane, readily obtained from the corresponding C-glycosyl ketones, were coupled with (+)- or (−)-camphorsultam glyoxylic oxime ether with diastereoselectivity ranging from 70:30 to 80:20. C-glucosyl allothreonine was obtained by cleavage of the camphorsultam moiety.

  C-葡萄糖基、甘露糖基和半乳糖基2-碘丙烷很容易从相应的C-糖基酮获得，与(+)-或(-)-樟脑磺内酰胺乙醛酸肟醚偶联，非对映选择性范围为70:30至80:20。 C-葡萄糖基别苏氨酸通过樟脑磺内酰胺部分的裂解获得。
• One-Step Synthesis of β-<i>C</i>-Glycosidic Ketones in Aqueous Media: The Case of 2-Acetamido Sugars
  作者：Marie-Christine Scherrmann、Nicolas Bragnier

  DOI：10.1055/s-2005-861816

  日期：——

  The one step synthesis of β-d-C-glycosidic ketones by condensation of pentane-2,4-dione with unprotected N-acetyl-d-gluco-, manno-, and galactosamine in alkaline aqueous media has been explored. N-Acetyl-d-gluco- and mannosamine gave, in good yield, a mixture of the two gluco and manno C-glycosidic ketones, which were separated by crystallization after acetylation, whereas N-acetyl-d-galactosamine afforded the galacto C-glycosidic ketone which was isolated as its acetylated derivative in 50% yield.

  研究人员探索了在碱性水介质中通过戊烷-2,4-二酮与未受保护的 N-乙酰基-d-葡糖、甘露糖和半乳糖胺缩合一步合成 δ-d-C-糖苷酮的方法。N- 乙酰基-d-葡糖和甘露胺以良好的收率得到了两种葡糖和甘露 C-糖苷酮的混合物，乙酰化后通过结晶将其分离，而 N- 乙酰基-d-半乳糖胺则得到了半乳糖 C-糖苷酮，并以 50%的收率分离出其乙酰化衍生物。