甲基6-O-(三苯基甲基)-ALPHA-D-吡喃甘露糖苷三苯甲酸酯 | 198338-59-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 中文名称: 甲基6-O-(三苯基甲基)-ALPHA-D-吡喃甘露糖苷三苯甲酸酯
• 中文别名: 5,5'-二硫代二水杨基&lt邻羟苄基&gt酸
• 英文名称: methyl 2,3,4-tri-O-benzoyl-6-O-trityl-α-D-mannopyranoside
• 英文别名: methyl 2,3,4-tri-O-benzoyl-6-trityl-α-D-mannopyranoside；methyl-(O²,O³,O⁴-tribenzoyl-O⁶-trityl-α-D-mannopyranoside)；Methyl-(O²,O³,O⁴-tribenzoyl-O⁶-trityl-α-D-mannopyranosid)；Methyl 2,3,4-tri-O-benzoyl-6-O-trityl-A-D-mannopyranoside；[(2R,3R,4S,5S,6S)-4,5-dibenzoyloxy-6-methoxy-2-(trityloxymethyl)oxan-3-yl] benzoate
• CAS: 198338-59-9
• 化学式: C₄₇H₄₀O₉
• 分子量: 748.829
• InChiKey: VJVBHUDMUNAIQS-KPPHSOHNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.3
• 重原子数：
  56
• 可旋转键数：
  16
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  107
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  甲基6-O-(三苯基甲基)-ALPHA-D-吡喃甘露糖苷三苯甲酸酯 在 盐酸 、 calcium sulfate 、 silver(l) oxide 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 72.0h， 生成 methyl 2,3,6-tri-O-benzoyl-4-O-methyl-α-D-glucopyranoside
  参考文献：
  名称：

  Studies on the substrate specificity of a GDP-mannose pyrophosphorylase from Salmonella enterica

  摘要：

  一系列甲氧基和去氧衍生物的甘霖糖吡喷酸酯（Manp-1P）经化学合成，研究了它们通过一种来自沙门氏菌（Salmonella enterica）的焦磷酸化酶（GDP-ManPP）能否转化为相应的鸟苷二磷酸甘霖糖（GDP-Manp）类似物的能力。对甲氧基类似物的评价表明，GDP-ManPP对C-2、C-3和C-4位置的庞大取代基不耐受，进而暗示这些位置被埋藏在酶活性位点内部。此外，6-甲氧基和6-去氧 Manp-1P 衍生物均是GDP-ManPP的良好或中等底物，因此表明 Manp-1P 底物的C-6 羟基不是与酶结合所必需的。综合考虑先前发表的其他研究成果，这种酶似乎具有潜在的用途，可用于化酶合成 GDP-Manp 类似物，这些类似物是用于研究以这种糖核苷酸为底物的酶的有用探针。

  DOI：

  10.3762/bjoc.8.136
• 作为产物：
  描述：

  甲基-D-丙噻 在 吡啶 作用下， 反应 60.0h， 生成 甲基6-O-(三苯基甲基)-ALPHA-D-吡喃甘露糖苷三苯甲酸酯
  参考文献：
  名称：

  脱氢丙氨酸的非经典 C-糖连接：C-糖氨基酸和 C-糖肽的合成

  摘要：

  在此，通过向迈克尔受体添加戊糖的 C5 自由基或己糖的 C6 自由基，报道了非经典的C糖键。C(sp 3 )–S 裂解的糖基噻蒽盐被开发为糖基自由基试剂。该反应为合成 β-糖基取代的非天然氨基酸以及肽的后期C糖修饰提供了一个有效的工具包。

  DOI：

  10.1039/d2cc06653j

文献信息

• Visible-Light-Mediated, Chemo- and Stereoselective Radical Process for the Synthesis of <i>C</i>-Glycoamino Acids
  作者：Peng Ji、Yueteng Zhang、Yongyi Wei、He Huang、Wenbo Hu、Patrick A. Mariano、Wei Wang

  DOI：10.1021/acs.orglett.9b00724

  日期：2019.5.3

  for efficient synthesis of C-glycosyl amino acids is described. Different from typical photoredox-catalyzed reactions of imines, the new process follows a pathway in which α-imino esters serve as electrophiles in chemoselective addition reactions with nucleophilic glycosyl radicals. The process is highlighted by the mild nature of the reaction conditions, the highly stereoselectivity attending C–C

  描述了一种有效合成C-糖基氨基酸的方法。与典型的亚胺的光氧化还原催化反应不同，该新方法遵循以下途径：α-亚氨基酯在与亲核糖基发生化学选择性加成反应中充当亲电试剂。反应条件的温和性质，伴随C–C键形成的高度立体选择性及其适用于使用武装和解除武装的戊糖和己糖衍生物进行C-糖基化反应的过程，突显了这一过程。
• TsOH-catalyzed acyl migration reaction of the Bz-group: innovative assembly of various building blocks for the synthesis of saccharides
  作者：Xing-Yong Liang、An-Lin Liu、Hua-Jun Shawn Fan、Lei Wang、Zhi-Ning Xu、Xin-Gang Ding、Bo-Shun Huang

  DOI：10.1039/d2ob02052a

  日期：——

  We developed an efficient method to achieve the regioselective acyl migration of benzoyl ester. In all the cases, the reactions required only the commercially available organic acid catalyst TsOH·H2O. This method enables the benzoyl group to migrate from secondary groups to primary hydroxyl groups, or from equatorial secondary hydroxyl groups to axial hydroxyl groups. The 1,2 or 1,3 acyl migration

  我们开发了一种有效的方法来实现苯甲酰酯的区域选择性酰基迁移。在所有情况下，反应只需要市售的有机酸催化剂 TsOH·H 2 O。该方法使苯甲酰基从仲羟基迁移到伯羟基，或从赤道仲羟基迁移到轴向羟基。1,2 或 1,3 酰基迁移可能通过五元和六元环邻位发生酸中间体。合成了范围广泛的正交保护单糖，它们是合成天然低聚糖的有用中间体。最后，为了证明该方法的实用性，组装了来自分枝杆菌细胞壁多糖的四糖部分。
• Removal of Acid-Labile Protecting Groups on Carbohydrates Using Water-Tolerant and Recoverable Vanadyl Triflate Catalyst
  作者：Ming-Chung Yan、Yeng-Nan Chen、Huan-Ting Wu、Chang-Ching Lin、Chien-Tien Chen、Chun-Cheng Lin

  DOI：10.1021/jo061881g

  日期：2007.1.1

  Acetal, trityl, and TBDMS protecting groups on saccharides were subjected to alcoholysis using a catalytic amount of vanadyl triflate in an MeOH-CH2Cl2 solvent system. The configuration at the anomeric positions of saccharides was retained, and no glycosidic bond cleavage and oxidation of sulfides were observed. The presented method was easily implemented, compatible with diverse functional groups, and regioselective in some cases.
• Detritylation of mono- and di-saccharide derivatives using ferric chloride hydrate
  作者：Xianglan Ding、Wei Wang、Fanzuo Kong

  DOI：10.1016/s0008-6215(97)00190-0

  日期：1997.10

  Quantitative detritylation of mono-and di-saccharide derivatives of diverse structure was achieved with FeCl3.6H(2)O in CH2Cl2 at room temperature. Benzyl, isopropylidene, isopropylthio, allyl, acetyl, and benzoyl O-protecting groups were not effected under the designated conditions. (C) 1997 Elsevier Science Ltd.
• Synthesis and Structure Elucidation of Benzoylated Deoxyfluoropyranosides
  作者：Aslan M. Esmurziev、Nebojsa Simic、Bård Helge Hoff、Eirik Sundby

  DOI：10.1080/07328303.2010.540055

  日期：2010.9

  Benzoylated deoxyfluoropyranosides have been synthesized, starting with protected, unprotected, or fluorinated precursors. Fluorination of eight derivatives was compared using DAST and Deoxo-Fluor as reagents. Deoxo-Fluor was found to be especially useful in the fluorination of methyl 2,3,4-O-tribenzoyl -D-mannopyranoside and -D-glucopyranoside, resulting in better yields and avoiding the 1,6-methoxy migration experienced with DAST for one derivative. The two reagents gave comparable yields in the fluorination of other methyl pyranosides, confirming Deoxo-Fluor as a safer alternative to DAST. Methyl -D-mannopyranoside underwent fluorination to yield the 4,6-difluorotalopyranoside and the corresponding cyclic sulfite. The NMR spectroscopic properties of 11 benzoyl deoxy-fluoropyranosides are reported.