2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside | 174314-08-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
• CAS: 174314-08-0
• 化学式: C₂₀H₃₂Cl₃NO₁₀Si
• 分子量: 580.919
• InChiKey: BPDZTHHRTUXWTL-DUQPFJRNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.96
• 重原子数：
  35.0
• 可旋转键数：
  10.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  135.69
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside 在 三氟化硼乙醚 作用下， 以 二氯甲烷 为溶剂， 反应 3.42h， 生成 ethyl 3,4,6-tri-O-acetyl-2-deoxy-1-thio-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
  参考文献：
  名称：

  N-Troc保护的糖基供体的糖基化。

  摘要：

  将N-Troc保护的（Troc = 2,2,2-三氯乙氧基羰基）葡萄糖胺和半乳糖胺糖基供体（1-O-乙酰基糖，溴糖和硫代糖苷）与相应的N-Phth保护的衍生物的糖基化为2 -（三甲基甲硅烷基）乙醇，2-溴乙醇，3-巯基丙酸甲酯，N-Fmoc保护的丝氨酸和2-（三甲基甲硅烷基）乙基6-O-苄基-2-脱氧-2-邻苯二甲酰亚胺-β-D-吡喃葡萄糖苷。N-Troc保护的供体比N-Phth保护的供体以更高的收率得到纯的β-糖苷。N-Troc保护基可通过用锌还原来去除，从而允许在同时包含N-Troc和N-Phth基团的寡糖中进行选择性N-脱保护。

  DOI：

  10.1016/0008-6215(95)00318-5
• 作为产物：
  描述：

  2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-D-glucopyranose 在 吡啶 、 2,4,6-三甲基吡啶 、 氢溴酸 、 silver trifluoromethanesulfonate 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 生成 2-(trimethylsilyl)ethyl 3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranoside
  参考文献：
  名称：

  Syntheses of 2-NBDG analogues for monitoring stereoselective uptake of d -glucose

  摘要：

  2-NBDG is a widely used fluorescent tracer for monitoring D-glucose uptake into single living cells. However, 2-NBDG alone is not sufficient for monitoring the net stereoselective uptake of D-glucose, unless its possible non-stereoselective uptake is properly evaluated. L-Glucose derivatives, which emit fluorescence distinct from that of 2-NBDG, should provide valuable information on the stereoselective uptake, when used with 2-NBDG in combination. In the present study, we synthesized Texas Red (sulforhodamine 101 acid)-coupled and [2-(benz-2-oxa-1,3-diazol-4-yl)amino]-coupled 2-deoxy-D-glucose, referred to as [2-TRG] and [2-BDG], respectively. These derivatives showed emission wavelength longer and shorter than that of 2-NBDG, respectively. 2-TRLG, an antipode of 2-TRG, proved to be an effective tracer for evaluating the extent of non-stereoselective uptake of 2-NBDG when used simultaneously with 2-NBDG. On the other hand, 2-BDG exhibited very weak fluorescence, but the application of a novel cross coupling in the presence of a benzoxadiazole group may be useful for the future development of effective glucose tracers. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2011.04.148

文献信息

• Synthetic Studies on Glycosphingolipids from Protostomia Phyla: Synthesis of Glycosphingolipids from the Parasite Schistosoma mansoni
  作者：Takayuki Kanaya、Satomi Yagi、Frank Schweizer、Tadahiro Takeda、Fumiyuki Kiuchi、Noriyasu Hada

  DOI：10.1248/cpb.58.811

  日期：——

  Synthetic access to three neutral glycosphingolipids from the parasite Schistosoma mansoni adult worm has been achieved. These structures differ significantly from those of other parasites and exhibit a unique structural motif termed “schisto-core” consisting of GalNAcβ1→4Glcβ1→sequence. We have synthesized glycosphingolipids, β-D-GalNAcp-(1→4)-β-D-Glcp-(1→1)Cer (1), β-D-GlcNAcp-(1→3)-β-D-GalNAcp-(1→4)-β-D-Glcp-(1→1)Cer (2) and β-D-Galp-(1→4)-β-D-GlcNAcp-(1→3)-β-D-GalNAcp-(1→4)-β-D-Glcp-(1→1)Cer (3).

  通过合成获得了来自曼氏血吸虫成虫的三种中性糖磷脂。这些糖磷脂的结构与其他寄生虫的糖磷脂有很大不同，表现出由 GalNAcβ1→4Glcβ1→ 序列组成的称为 "裂核 "的独特结构基团。我们合成了糖磷脂--β-<小>D-GalNAcp-(1→4)-β-<小>D-Glcp-(1→1)Cer (1)、β-D-GlcNAcp-(1→3)-β-D-GalNAcp-(1→4)-β-D-Glcp-(1→1)Cer (2) 和 β-D-Galp-(1→4)-β-D-GlcNAcp-(1→3)-β-D-GalNAcp-(1→4)-β-D-Glcp-(1→1)Cer (3)。
• The synthesis of oligosaccharides containing internal and terminal Galβ1-3GlcNAcβ fragments
  作者：V. V. Severov、G. V. Pazynina、T. V. Ovchinnikova、N. V. Bovin

  DOI：10.1134/s1068162015020120

  日期：2015.3

  Oligosaccharides Gal beta 1-3GlcNAc beta-sp, GlcNAc beta 1-3Gal beta 1-3GlcNAc beta-sp, Gal beta 1-3GlcNAc beta 1-3Gal beta 1-3GlcNAc beta-sp, Gal beta 1-3GlcNAc beta 1-3Gal beta 1-4GlcNAc beta-sp, Gal beta 1-3GlcNAc beta 1-6Gal beta 1-4GlcNAc beta-sp (sp = O(CH2)(3)NH2 or O(CH2)(2)NH2) were synthesized using glycosylation with N-Troc-protected derivatives of glucosamine or disaccharide Le(c).