octyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside | 187139-92-0

• 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: octyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside
• CAS: 187139-92-0
• 化学式: C₂₂H₃₆O₉S
• 分子量: 476.588
• InChiKey: XIROMIKWUKFPAA-LXHROKJGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  32.0
• 可旋转键数：
  13.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  114.43
• 氢给体数：
  0.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  octyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside 在 吡啶 、 咪唑 、 氢氟酸 、 sodium methylate 作用下， 以 吡啶 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 40.42h， 生成 octyl 2-O-benzoyl-4-O-(1-fluoro-1,1,3,3-tetraisopropyl-1,3-disiloxane-3-yl)-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of octyl O- and S-glycosides related to the GPI anchor of Trypanosoma brucei and their in vitro galactosylation by trypanosomal α-galactosyltransferases

  摘要：

  Octyl O- and S-glycosides of mono- to tri-saccharides related to the core structure alpha-D-Manp-(1-->2)-alpha-D-Manp-(1-->6)-alpha-D-Manp of the GPI anchor of Trypanosoma brucei have been prepared via regioselective protodesilylation and glycodesilylation of octyl O- and S-glycosides of 2-O-benzoyl-4,6-O-(1,1,3,3-tetraisopropyl-1,3-disiloxane-1,3-diyl)-alpha-D-mannopyranoside. The synthetic saccharides have been used as substrates for enzymatic alpha-galactosylation with membrane fractions of bloodstream forms of T. brucei strain 427 variants MIT at 1.4, MIT at 1.2, and MIT at 1.5, respectively. (C) 1996 Elsevier Science Ltd.

  DOI：

  10.1016/s0008-6215(96)00215-7
• 作为产物：
  描述：

  1-溴辛烷 、 1,2,3,4,6-O-五乙酰基-Alpha-甘露糖 在 硫脲 、 三乙胺 作用下， 以 乙腈 为溶剂， 反应 3.25h， 生成 octyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside
  参考文献：
  名称：

  通过S-糖基异硫脲盐从未保护的醛糖中制备硫糖苷的修改的一锅方案*

  摘要：

  据报道，一种有效的一锅法方案可直接从未保护的还原糖开始，通过S-糖基异硫脲盐直接制备硫糖苷。在这种一锅法中，BF3·OEt2已被用作糖的全O-乙酰化和糖的过O-乙酸转化为S-糖基异硫脲盐的通用催化剂，该盐可与烷化剂反应在碱的存在下以优异的产率提供硫代糖苷。* CDRI通讯号 6767.作者对这项工作做出了同等的贡献。

  DOI：

  10.1080/07328300500256775

文献信息

• Synthesis of alkyl and cycloalkyl α-d-mannopyranosides and derivatives thereof and their evaluation in the mycobacterial mannosyltransferase assay
  作者：Monika Poláková、Martina Beláňová、Ladislav Petruš、Katarína Mikušová

  DOI：10.1016/j.carres.2010.03.011

  日期：2010.7

  The synthesis of a series of alkyl (having from C6 to C20 aglycones), cyclohexyl, and cyclohexylalkyl alpha-d-mannopyranosides, 6-deoxygenated analogs, thioglycosides, and sulfones derived thereof, is reported. Here, under the in vitro assay conditions used, none of the 15 tested compounds acted as an inhibitor of the mannose transfer catalyzed by the enzymes present in mycobacterial membrane and cell

  据报道，合成了一系列烷基（具有从C 6至C 20的糖苷配基），环己基和环己基烷基α-d-甘露吡喃糖苷，6-脱氧类似物，硫代糖苷及其衍生的砜。在此，在所用的体外测定条件下，15种被测化合物均未充当分枝杆菌膜和细胞壁组分中存在的酶催化的甘露糖转移的抑制剂。在分枝杆菌甘露糖基转移酶反应中，包含较短的脂族，最多8个碳原子长的线性或环状糖苷的甘露吡喃糖苷用作受体底物。与砜相反，该硫糖苷表现出相似的行为，而后者基本上未被分枝杆菌酶所识别。6-脱氧糖苷未被酶处理，
• Synthesis, purification and liquid-crystalline behaviour of several alkyl 1-thio-d-glycopyranosides
  作者：Saskia A. Galema、Jan B.F.N. Engberts、Henk A. van Doren

  DOI：10.1016/s0008-6215(97)00185-7

  日期：1997.10

  This paper describes the synthesis, purification, and liquid-crystalline behaviour of a series of alkyl 1-thioglycopyranosides. The synthesis of these derivatives was carried out via a Lewis acid mediated coupling of the fully acetylated monosaccharide with an alkanethiol. The choice of the Lewis acid depends on the configuration of AcO-2, The carbohydrate-derived surfactants exhibit thermotropic liquid-crystalline behaviour. The alkyl 1-thioglycopyranosides form the expected smectic A phases upon heating. The clearing temperatures vary with alkyl chain length which is in accordance with the accepted model for the S-A phase of amphiphilic carbohydrate mesogens. For the alkyl 1-thiotalopyranosides, the clearing points are much lower than expected, presumably due to the formation of an intramolecular hydrogen bond in the talose moiety. (C) 1997 Elsevier Science Ltd.