1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glycerol | 544686-85-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glycerol
• 英文别名: (2S)-3-[tert-butyl(diphenyl)silyl]oxy-2-[(4-methoxyphenyl)methoxy]propan-1-ol
• CAS: 544686-85-3
• 化学式: C₂₇H₃₄O₄Si
• 分子量: 450.65
• InChiKey: BLFKIOFLJWLBGG-DEOSSOPVSA-N

物化性质

• 沸点：
  535.7±50.0 °C(Predicted)
• 密度：
  1.10±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glycerol 在 4-二甲氨基吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘苯二乙酸 、 (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylaminomorpholinocarbenium hexafluorophosphate 、 sodium methylate 、 四丁基碘化铵 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 、 氟化氢吡啶 、 N,N-二异丙基乙胺 、 2,4,6-三叔丁基嘧啶 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 197.0h， 生成 benzyl (1-O-palmityl-2-O-(4-methoxybenzyl)-sn-glyceryl 2,3,4-tri-O-benzyl-α-D-glucopyranosid)uronate
  参考文献：
  名称：

  Synthesis, Structural Elucidation, And Biochemical Analysis of Immunoactive Glucuronosyl Diacylglycerides of Mycobacteria and Corynebacteria

  摘要：

  Glucuronosyl diacylglycerides (GlcAGroAc(2)) are functionally important glycolipids and membrane anchors for cell wall lipoglycans in the Corynebacteria. Here we describe the complete synthesis of distinct acyl-isoforms of GlcAGroAc(2) bearing both acylation patterns of (R)-tuberculostearic acid (C-19:0) and palmitic acid (C-16:0) and their mass spectral characterization. Collision-induced fragmentation mass spectrometry identified characteristic fragment ions that were used to develop "rules" allowing the assignment of the acylation pattern as C-19:0 (sn-1), C-16:0 (sn-2) in the natural product from Mycobacterium smegmatis, and the structural assignment of related C-18:1 (sn-1), C-16:0 (sn-2) GlcAGroAc(2) glycolipids from M. smegmatis and Corynebacterium glutamicum. A synthetic hydrophobic octyl glucuronoside was used to characterize the GDP-mannose-dependent mannosyltransferase MgtA from C. g/utamicum that extends GlcAGroAc(2). This enzyme is an Mg2+/Mn2+-dependent metalloenzyme that undergoes dramatic activation upon reduction with dithiothreitol.

  DOI：

  10.1021/jo302508e
• 作为产物：
  描述：

  tert-Butyl-{(S)-2-(4-methoxy-benzyloxy)-3-[((E)-propenyl)oxy]-propoxy}-diphenyl-silane 在 盐酸 作用下， 以 丙酮 为溶剂， 反应 0.17h， 以10.5 g的产率得到1-O-(tert-butyldiphenylsilyl)-2-O-(4-methoxybenzyl)-sn-glycerol
  参考文献：
  名称：

  Synthesis of structural variants of Staphylococcus aureus lipoteichoic acid (LTA)

  摘要：

  Based on 1,2-O-isopropylidene-sn-glyerol, which is readily available from D-mannitol, five chiral building blocks for the construction of structural variants of Staphylococcus aureus LTA designed and synthesized. Ligation of these building blocks led readily to the target molecules 1 and 2. They demonstrated that the D-alanine residues at the glycerophosphate backbone are decisive for the activation of the immune system. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.11.070

文献信息

• Regioselective phosphorylation of myo-inositol with BINOL-derived phosphoramidites and its application for protozoan lysophosphatidylinositol
  作者：Toshihiko Aiba、Masaki Sato、Daichi Umegaki、Takanori Iwasaki、Nobuaki Kambe、Koichi Fukase、Yukari Fujimoto

  DOI：10.1039/c6ob01062h

  日期：——

  BINOL-derived phosphoramidites enabled a regioselective phosphorylation of myo-inositol. The method was applied for the first total synthesis of a protozoan lysophosphatidylinositol, EhPIa.

  BINOL衍生的磷酰胺使得对肌醇的选择性磷酸化成为可能。该方法被首次应用于原生动物溶酶磷脂肌醇的全合成，EhPIa。
• Convergent Synthesis of Digalactosyl Diacylglycerols
  作者：Shinsuke Inuki、Junichiro Kishi、Emi Kashiwabara、Toshihiko Aiba、Yukari Fujimoto

  DOI：10.1021/acs.orglett.7b03043

  日期：2017.12.15

  diacylglycerols (DGDGs), which have both a galactose–galactose α(1→6)-linkage and a galactose–glycerol β-linkage along with a diacylglycerol containing various kinds of fatty acids, have been accomplished. In order to achieve a concise synthesis, we chose to use allylic protective groups as permanent protective groups. We have also achieved α- and β-selective glycosylations for the respective linkages with

  已经完成了具有半乳糖-半乳糖α（1→6）-键和半乳糖-甘油β-键以及含有多种脂肪酸的二酰基甘油的高效二聚半乳糖基二酰基甘油（DGDG）的聚合化学合成。为了实现简洁的合成，我们选择使用烯丙基保护基作为永久保护基。作为关键步骤，我们还以高收率获得了各自键的α-和β-选择性糖基化。
• [EN] NEW IMMUNOSTIMULATORY COMPOUNDS<br/>[FR] NOUVEAUX COMPOSÉS IMMUNOSTIMULANTS
  申请人：BERNHARD NOCHT INST FÜR TROPENMEDIZIN

  公开号：WO2016046419A1

  公开（公告）日：2016-03-31

  The present invention relates to novel immunostimulatory molecules which are derived from the intestinal protozoan Entamoeba histolytica.The compounds have been found to be useful for enhancing and/or inducing an immune response in a subject in need thereof. Specifically, the compounds have been found to be useful for the treatment of cancer diseases, such as breast cancer, and parasitic diseases, such as leishmaniasis. The invention also provides pharmaceutical compositions comprising the novel compounds.

  本发明涉及一种新型的免疫刺激分子，这些分子源自肠道原虫组织阿米巴。已发现这些化合物可用于增强和/或引起需要免疫反应的受体的免疫反应。具体来说，这些化合物已被发现可用于治疗癌症疾病，如乳腺癌，以及寄生虫病，如利什曼病。本发明还提供了包含这些新型化合物的制药组合物。
• A Staphylococcus aureus lipoteichoic acid (LTA) derived structural variant with two diacylglycerol residues
  作者：A STADELMAIER、I FIGUEROAPEREZ、S DEININGER、S VONAULOCK、T HARTUNG、R SCHMIDT

  DOI：10.1016/j.bmc.2006.05.055

  日期：2006.9.15

  Based on 1,2-O-isopropylidene-sn-glycerol five chiral building blocks containing differently modified glycerol residues were required for the synthesis of the target molecule 2. One of these building blocks is diacylglyceryl beta-gentiobioside carrying a phosphite residue at 6b-O position. Ligation of these five building blocks led to the desired glycerol phosphate backbone to which D-alanyl residues were attached, thus generating after O-deprotection the target molecule 2, a bisamphiphilic structural variant of Staphylococcus aureus LTA. This compound displayed higher potency in terms of cytokine release by human blood leukocytes than the monoamphiphilic variant LTA. (c) 2006 Elsevier Ltd. All rights reserved.
• Synthesis, Structural Elucidation, And Biochemical Analysis of Immunoactive Glucuronosyl Diacylglycerides of Mycobacteria and Corynebacteria
  作者：Benjamin Cao、Xingqiang Chen、Yoshiki Yamaryo-Botte、Mark B. Richardson、Kirstee L. Martin、George N. Khairallah、Thusita W.T. Rupasinghe、Roisin M. O’Flaherty、Richard A.J. O’Hair、Julie E. Ralton、Paul K. Crellin、Ross L. Coppel、Malcolm J. McConville、Spencer J. Williams

  DOI：10.1021/jo302508e

  日期：2013.3.15

  Glucuronosyl diacylglycerides (GlcAGroAc(2)) are functionally important glycolipids and membrane anchors for cell wall lipoglycans in the Corynebacteria. Here we describe the complete synthesis of distinct acyl-isoforms of GlcAGroAc(2) bearing both acylation patterns of (R)-tuberculostearic acid (C-19:0) and palmitic acid (C-16:0) and their mass spectral characterization. Collision-induced fragmentation mass spectrometry identified characteristic fragment ions that were used to develop "rules" allowing the assignment of the acylation pattern as C-19:0 (sn-1), C-16:0 (sn-2) in the natural product from Mycobacterium smegmatis, and the structural assignment of related C-18:1 (sn-1), C-16:0 (sn-2) GlcAGroAc(2) glycolipids from M. smegmatis and Corynebacterium glutamicum. A synthetic hydrophobic octyl glucuronoside was used to characterize the GDP-mannose-dependent mannosyltransferase MgtA from C. g/utamicum that extends GlcAGroAc(2). This enzyme is an Mg2+/Mn2+-dependent metalloenzyme that undergoes dramatic activation upon reduction with dithiothreitol.