9-decenyl α-D-mannopyranoside | 155197-26-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 9-decenyl α-D-mannopyranoside
• 英文别名: dec-9-enyl a-D-mannopyranoside；mannose；(2S,3S,4S,5S,6R)-2-dec-9-enoxy-6-(hydroxymethyl)oxane-3,4,5-triol
• CAS: 155197-26-5
• 化学式: C₁₆H₃₀O₆
• 分子量: 318.411
• InChiKey: LLSMPAPCRPMKQQ-OWYFMNJBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  22
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  99.4
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9-decenyl α-D-mannopyranoside 在 2,4,6-三甲基吡啶 、 盐酸 、 silver trifluoromethanesulfonate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 氯仿 为溶剂， 反应 23.5h， 生成
  参考文献：
  名称：

  Nikolaev, Andrey V.; Rutherford, Trevor J.; Ferguson, Michael A. J., Journal of the Chemical Society. Perkin transactions I, 1995, # 16, p. 1977 - 1988

  摘要：

  DOI：
• 作为产物：
  描述：

  2,3,4,6-四-O-乙酰基-1-溴-Alpha-D-甘露糖 在 sodium methylate 、 氰化汞 、 mercury dibromide 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 生成 9-decenyl α-D-mannopyranoside
  参考文献：
  名称：

  Nikolaev, Andrey V.; Rutherford, Trevor J.; Ferguson, Michael A. J., Journal of the Chemical Society. Perkin transactions I, 1995, # 16, p. 1977 - 1988

  摘要：

  DOI：

文献信息

• CARBOHYDRATE CONJUGATES AS DELIVERY AGENTS FOR OLIGONUCLEOTIDES
  申请人：Alnylam Pharmaceuticals, Inc.

  公开号：US20160051691A1

  公开（公告）日：2016-02-25

  The present invention provides iRNA agents comprising at least one subunit of the formula (I): wherein: A and B are each independently for each occurrence O, N(R N ) or S; X and Y are each independently for each occurrence H, OH, a hydroxyl protecting group, a phosphate group, a phosphodiester group, an activated phosphate group, an activated phosphite group, a phosphoramidite, a solid support, —P(Z′)(Z″)O-nucleoside, —P(Z′)(Z″)O-oligonucleotide, a lipid, a PEG, a steroid, a lipophile, a polymer, —P(Z′)(Z″)O-Linker-OP(Z′″)(Z″″)O-oligonucleotide, a nucleotide, an oligonucleotide, —P(Z′)(Z″)-formula(I), —P(Z′)(Z″)— or -Linker-R; R is L G , -Linker-L G , or has the structure shown below: L G is independently for each occurrence a carbohydrate, e.g., monosaccharide, disaccharide, trisaccharide, tetrasaccharide, oligosaccharide, polysaccharide; R N is independently for each occurrence H, methyl, ethyl, propyl, isopropyl, butyl, or benzyl; and Z′, Z″, Z′″ and Z″″ are each independently for each occurrence O or S.

  本发明提供了包含至少一个式(I)的亚单位的iRNA试剂： 其中： A和B分别独立于每次出现O、N(RN)或S； X和Y分别独立于每次出现H、OH、一个羟基保护基团、一个磷酸基团、一个磷酸二酯基团、一个活化磷酸基团、一个活化亚磷酸基团、一个磷酰胺基团、一个固相支持、-P(Z')(Z″)O-核苷、-P(Z')(Z″)O-寡核苷酸、一个脂质、一个PEG、一个类固醇、一个亲脂物质、一个聚合物、-P(Z')(Z″)O-连接子-OP(Z′″)(Z″″)O-寡核苷酸、一个核苷酸、一个寡核苷酸、-P(Z')(Z″)-式(I)、-P(Z')(Z″)-或-连接子-R； R是LG、-连接子-LG，或具有下面所示结构： LG独立于每次出现的是一种碳水化合物，例如，单糖、双糖、三糖、四糖、寡糖、多糖； RN独立于每次出现的是H、甲基、乙基、丙基、异丙基、丁基或苄基； Z'、Z″、Z′″和Z″″分别独立于每次出现的是O或S。
• Synthetic tools for the characterization of galactofuranosyl transferases: glycosylations via acylated glycosyl iodides
  作者：Luciana Baldoni、Carla Marino

  DOI：10.1016/j.carres.2013.03.032

  日期：2013.6

  With the aim of developing synthetic tools for the characterization of galactofuranosyltransferases, the synthesis of 9-decenyl glycosides of D-Manp, D-Galf, and beta-D-Galf-(1 -> 3)-D-Manp was targeted. The interest in the alkenyl aglycone arises via potential conjugation reactions, once the terminal double bond has been conveniently functionalized. The glycosylation of beta-D-Galf-(1 -> 3)-D-Manp was attempted by two different approaches: the trichloroacetimidate method and the glycosylation via the glycosyl iodide. The conditions for the latter were established on the basis of glycosylation assays of per-O-acetylmannose. On the other hand, the study of glycosylation reactions via per-O-benzoylated galactofuranosyl iodide confirms the versatility of glycosyl iodides as donors. (C) 2013 Elsevier Ltd. All rights reserved.
• Synthesis and anti-tumor activity of carbohydrate analogues of the tetrahydrofuran containing acetogenins
  作者：Stewart Bachan、K.A. Tony、Akira Kawamura、Diego Montenegro、Anjali Joshi、Himanshu Garg、David R. Mootoo

  DOI：10.1016/j.bmc.2013.08.027

  日期：2013.11

  The tetrahydrofuran (THF) containing annonaceous acetogenins (AAs) are attractive candidates for drug development because of their potent cytotoxicity against a wide range of tumors and their relatively simple and robust structures. Replacement of the THF segment with a sugar residue may deliver analogues with improved tumor selectivity and pharmacokinetics and are therefore attractive for drug development. As a first test to the feasibility of such structures, a set of such monosaccharide analogues was synthesized and assayed against four human tumor cell lines, cervical (HeLa), breast (MDA-MB231), T-cell leukemia (Jurkat) and prostate (PC-3). Certain analogues showed low micromolar activity that was comparable to a structurally similar, naturally occurring mono-THF acetogenin. A preliminary examination of the structure-activity profile of these carbohydrate analogues suggests that they have a similar mechanism of action as their THF congeners. (C) 2013 Elsevier Ltd. All rights reserved.
• Nikolaev, Andrey V.; Rutherford, Trevor J.; Ferguson, Michael A. J., Journal of the Chemical Society. Perkin transactions I, 1995, # 16, p. 1977 - 1988
  作者：Nikolaev, Andrey V.、Rutherford, Trevor J.、Ferguson, Michael A. J.、Brimacombe, John S.

  DOI：——

  日期：——