1,2-di-O-benzyl-3-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-sn-glycerol | 58438-08-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: 1,2-di-O-benzyl-3-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-sn-glycerol
• 英文别名: (2R)-1,2-di-O-benzyl-3-O-(2′,3′,4′,6′-tetra-O-acetyl-β-D-glucopyranosyl)glycerol；1,2-di-O-benzyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-sn-glycerol；1,2-di-O-benzyl-sn-glyceryl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
• CAS: 58438-08-7
• 化学式: C₃₁H₃₈O₁₂
• 分子量: 602.636
• InChiKey: DCRUXYFMHOHXAW-IOTQWNSASA-N

物化性质

• 沸点：
  648.3±55.0 °C(Predicted)
• 密度：
  1.25±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.89
• 重原子数：
  43.0
• 可旋转键数：
  15.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  142.12
• 氢给体数：
  0.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  1,2-di-O-benzyl-3-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-sn-glycerol 在 N-甲基咪唑 、 4-二甲氨基吡啶 、 hydrazine hydrate 、 偶氮二甲酸二异丙酯 、 palladium 10% on activated carbon 、 氢气 、 碘 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三乙胺 、 乙酰氯 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 甲苯 为溶剂， 反应 5.32h， 生成 (2R)-3-O-β-D-glucopyranosyl-2-O-octanoylamino-1-O-palmitoylglycerol
  参考文献：
  名称：

  Synthesis of N-Oxyamide-Linked Neoglycolipids

  摘要：

  N-Oxyamide-containing compounds have shown improved metabolic stability and interesting secondary structures due to the good hydrogen bond-donating property of N-oxyamide. beta-Glucolipids linked by the N-oxyamide bond have been successfully synthesized as novel mimics of glycoglycerolipids and glycosphingolipids.

  DOI：

  10.1021/jo502128h
• 作为产物：
  描述：

  1,2,5,6-tetra-O-benzyl-3,4-O-isopropylidene-D-mannitol 在 盐酸 、 sodium periodate 、 mercury(II) cyanide 、 mercury dibromide 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 8.0h， 生成 1,2-di-O-benzyl-3-O-(2',3',4',6'-tetra-O-acetyl-β-D-glucopyranosyl)-sn-glycerol
  参考文献：
  名称：

  Synthesis of N-Oxyamide-Linked Neoglycolipids

  摘要：

  N-Oxyamide-containing compounds have shown improved metabolic stability and interesting secondary structures due to the good hydrogen bond-donating property of N-oxyamide. beta-Glucolipids linked by the N-oxyamide bond have been successfully synthesized as novel mimics of glycoglycerolipids and glycosphingolipids.

  DOI：

  10.1021/jo502128h

文献信息

• Synthesis of phosphatidyl-β-glucosyl glycerol containing a dioleoyl diglyceride moiety
  作者：C.A.A. van Boeckel、G.M. Visser、J.H. van Boom

  DOI：10.1016/s0040-4020(01)82350-4

  日期：1985.1

  in a two step procedure, to afford compound ; (c) a 2,4-dichlorophenyl protected phosphatidic acid derivative . Compound could be selectively coupled to the primary hydroxyl function of to afford the fully protected glycophospholipid . Finally, removal of the 2,4-dichlorophenyl and TIPS protecting groups from was performed with syn-4-nitrobenzaldoximate and fluoride ions, respectively, to afford glycophospholipid

  描述了磷脂酰-β-葡萄糖基甘油二酸酯的制备。糖脂的合成是通过以下方法完成的：（a）暂时保留左旋糖基的葡糖羟基功能，然后可以将其转化为被二油酰基取代的衍生物；（b）在两步法中，四异丙基二硅氧烷-1，3-二基（TIPS）基团保护其的3'-和4'-羟基，得到化合物；（c）2，4-二氯苯基保护的磷脂酸衍生物。化合物可以选择性地与的伯羟基功能偶合，以提供充分保护的糖磷脂。最后，去除2,4-二氯苯基和TIPS保护基分别用4-硝基苯并氧肟酸和氟离子进行操作，得到糖脂。
• Mycobacterium tuberculosis β-gentiobiosyl diacylglycerides signal through the pattern recognition receptor Mincle: total synthesis and structure activity relationships
  作者：Mark B. Richardson、Shota Torigoe、Sho Yamasaki、Spencer J. Williams

  DOI：10.1039/c5cc04773k

  日期：——

  Gentiobiosyl diglycerides fromMycobacterium tuberculosisare shown to signal through Mincle; structure–activity relationships reveal analogues with enhanced potency.

  结核分枝杆菌中的甘露二糖基二甘油酸被证明通过Mincle信号传导；结构-活性关系揭示出具有增强效力的类似物。
• Lilioside C, a glycerol glucoside from Lilium lancifolium
  作者：Miyuki Kaneda、Kiyoyasu Mizutani、Keiko Tanaka

  DOI：10.1016/0031-9422(82)80087-3

  日期：——

  Abstract A new glycerol glucoside, lilioside C, has been isolated from the leaves and stems of Lilium lancifolium . Its structure including the configuration of the aglycone moiety has been elucidated by chemical and spectroscopic means and by its synthesis.

  摘要 从百合的叶和茎中分离得到一种新的甘油葡萄糖苷，百合苷C。其结构包括苷元部分的构型已通过化学和光谱手段及其合成阐明。
• A hydrophobic disordered peptide spontaneously anchors a covalently bound RNA hairpin to giant lipidic vesicles
  作者：Alexandra Le Chevalier Isaad、Paolo Carrara、Pasquale Stano、Kollappillil S. Krishnakumar、Dominique Lafont、Alexandra Zamboulis、René Buchet、Denis Bouchu、Florian Albrieux、Peter Strazewski

  DOI：10.1039/c4ob00721b

  日期：——

  Exergonic compartmentation of nucleic acids to liposomes through conjugation with peptides lends experimental support to early evolvable RNA–peptide ‘collaboration’.

  核酸通过与肽共轭形成脂质体的外源性分隔，为早期可进化的RNA-肽“协作”提供了实验支持。
• Synthesis and mesogenic properties of glycosyl diacylglycerols
  作者：H.M von Minden、M Morr、G Milkereit、E Heinz、V Vill

  DOI：10.1016/s0009-3084(01)00202-x

  日期：2002.1

  We synthesised glycosyl diacylglycerols bearing unsaturated or chiral methyl branched fatty acid chains. The thermotropism was measured with polarising microscopy and additionally the lyotropism with the contact preparation method. The synthesised compounds displayed thermotropic S-A (lamellar), cubic and columnar phases and investigation of the lyotropic phase behaviour led to the observation of inverted bicontinuous cubic V-H phases, lamellar L-x phases and normal bicontinuous cubic V-I phases, The phases are discussed with respect to the chemical structures that have been varied systematically to derive structure-property relationships. (C) 2002 Elsevier Science Ireland Ltd. All rights reserved.