1,2,3,4,6-penta-O-benzoyl-β-D-mannopyranose

• 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: 1,2,3,4,6-penta-O-benzoyl-β-D-mannopyranose
• 英文别名: 1,2,3,4,6-tetra-O-benzoyl-β-D-mannopyranose；Penta-O-benzoyl-β-D-mannopyranose；1,2,3,4,6-PENTA-O-BENZOYL-beta-D-MANNOPYRANOSE；[(2R,3R,4S,5S,6S)-3,4,5,6-tetrabenzoyloxyoxan-2-yl]methyl benzoate
• 化学式: C₄₁H₃₂O₁₁
• 分子量: 700.698
• InChiKey: JJNMLNFZFGSWQR-ZEHPTFAOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.9
• 重原子数：
  52
• 可旋转键数：
  16
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  141
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  1,2,3,4,6-penta-O-benzoyl-β-D-mannopyranose 在 氢溴酸 、 溶剂黄146 、 1,2-二氯乙烷 作用下， 生成 methyl 2,3,4,6-tetra-O-benzoyl-α-D-mannopyranoside
  参考文献：
  名称：

  The Reaction of 2,3,4,6-Tetrabenzoyl-α-D-glucopyranosyl Bromide and 2,3,4,6-Tetrabenzoyl-α-D-mannopyranosyl Bromide with Methanol. Certain Benzoylated Derivatives of D-Glucose and D-Mannose

  摘要：

  DOI：

  10.1021/ja01161a091
• 作为产物：
  描述：

  D-甘露糖 、 苯甲酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 以84%的产率得到1,2,3,4,6-penta-O-benzoyl-β-D-mannopyranose
  参考文献：
  名称：

  3-(Dimethylamino)-1-propylamine: A Cheap and Versatile Reagent for Removal of Byproducts in Carbohydrate Chemistry

  摘要：

  Inexpensive 3-(dimethylamino)-1-propylamine (DMAPA) was found to be effective in anomeric deacylation reactions giving 1-O deprotected sugars in high yield as precursors for the formation of imidate glycosyl donors. DMAPA was also found to be useful for removing excess reagents such as benzoyl chloride, tosyl chloride, and 2,2,2-trifluoro-N-phenylacetimidoyl chloride. The deacylation reaction could be conducted in moist THF and did not require chromatographic purification since an acidic wash was sufficient to remove excess reagent and the formed byproduct.

  DOI：

  10.1021/acs.orglett.5b00041

文献信息

• Benzoylated ethyl 1-thioglycosides: direct preparation from per-O-benzoylated sugars
  作者：Deepak Sail、Pavol Kováč

  DOI：10.1016/j.carres.2012.05.012

  日期：2012.8

  the beta-benzoate predominated. Treatment of the foregoing compounds with EtSH at slightly elevated temperature (50-60 degrees C) in the presence of BF(3).Et(2)O as a promoter gave the corresponding ethyl 1-thio glycosides in high yields. The alpha-products predominated in all cases in the anomeric mixtures formed. Individual products of all reactions were isolated by chromatography, they were obtained

  D-葡萄糖、乳糖、麦芽糖和蜜二糖用 Bz(2)O-Et(3)N 试剂苯甲酰化，得到完全苯甲酰化的 β 产品。在相同条件下，D-甘露糖产生了以 β-苯甲酸酯为主的混合物。在BF(3).Et(2)O作为促进剂存在下，在稍微升高的温度(50-60℃)下用EtSH处理上述化合物，以高产率得到相应的乙基1-硫代糖苷。在所有情况下，在所形成的异头混合物中，α-产物占主导地位。所有反应的各个产物均通过色谱法分离，获得分析纯状态的产物，并通过 (1)H 和 (13)C NMR 数据和物理常数进行充分表征。
• Manipulation of free carbohydrates via stannylene acetals. Preparation of β-per-O-acyl derivatives of d-mannose, l-rhamnose, 6-O-trityl-d-talose, and d-lyxose
  作者：György Hodosi、Pavol Kováč

  DOI：10.1016/s0008-6215(97)00155-9

  日期：1997.9

  Abstract A simple and high-yielding method for the preparation of 1- O - β -acyl derivatives of carbohydrates with an axial OH group at C-2 is described. It utilizes the property of unprotected carbohydrates to preferentially form 1,2- O - cis stannylene acetals, when treated with dibutyltin oxide. These acetals can be acylated with retention of configuration at the anomeric position.

  摘要描述了一种简单高效的方法，用于制备在C-2处带有轴向OH基的碳水化合物的1- O-β-酰基衍生物。当用二丁基氧化锡处理时，它利用未保护的碳水化合物的特性优先形成1,2-O-顺式亚锡缩醛。这些缩醛可以被酰化，并保持在异头位置的构型。
• Synthetic Studies on Glycosphingolipids from Protostomia Phyla: Synthesis of Neogala-Series Glycolipid Analogues Containing a Mannose Residue from the Earthworm Pheretima hilgendorfi.
  作者：Noriyasu HADA、Akiko MATSUSAKI、Mutsumi SUGITA、Tadahiro TAKEDA

  DOI：10.1248/cpb.47.1265

  日期：——

  Two kinds of glycosphingolipid analogues from the earthworm Pheretima hilgendorfi were synthesized as follows : the trisaccharide 2-(tetradecyl)hexadecyl α-D-mannopyranosyl-(1→4)-β-D-galactopyranosyl-(1→6)-β-D-galactopyranoside (13) and the tetrasaccharide 2-(tetradecyl) hexadecyl α-D-galactopyranosyl-(1→6)-[α-D-mannopyranosyl-(1→4)]-β-D-galactopyranosyl-(1→6)-β-D-galactpyranoside (20) were synthesized by stepwise condensation of suitably protected monosaccharide units. A 2-(trimethylsilyl)ethyl 2, 3, 4-tri-O-benzoyl-β-D-galactopyranoside derivative (5) was used as the glycosyl acceptor and thiophenyl derivatives of D-galactose and D-mannose were used as donors respectively.

  从蚯蚓 Pheretima hilgendorfi 中合成了以下两种糖磷脂类似物：三糖 2-(十四烷基)十六烷基 α-D-吡喃甘露糖基-(1→4)-β-D-吡喃半乳糖基-(1→6)-β-D-吡喃半乳糖苷 (13) 和四糖 2-(十四烷基)十六烷基 α-D-半乳糖苷-(1→6)-[α-D-吡喃甘露糖基-(1→4)]-β-D-吡喃半乳糖苷-(1→6)-β-D-吡喃半乳糖苷(20)是通过逐步缩合适当保护的单糖单元合成的。2-(trimethylsilyl)ethyl 2, 3, 4-tri-O-benzoyl-β-D-galactopyranoside 衍生物 (5) 用作糖基受体，D-半乳糖和 D-甘露糖的硫代苯衍生物分别用作供体。
• Deciphering the conformation of C-linked α-D-mannopyranosides and their application toward the synthesis of low nanomolar E. coli FimH ligands
  作者：Leila Mousavifar、Gérard Vergoten、René Roy

  DOI：10.24820/ark.5550190.p010.783

  日期：——

  relative conformational energies of the key intermediate was evaluated by molecular modelingwhich showed the conventional 4C1chair conformation to be the lowest energy conformer. This finding was also confirmed by NMR and X-ray crystallography. The perbenzoylated C-allyl mannoside was also converted into 1,1’-biphenyl analogues using a palladium-catalyzed Heck reaction. Two of the resulting minor reaction

  某些符号无法重现。对于完整的摘要，请参阅原始文章 C-烯丙基 α–D-甘露糖苷通过多种途径制备，以确定 α-异头物的最佳途径。通过分子建模评估了关键中间体的相对构象能量，表明常规的4C1椅子构象是能量最低的构象异构体。这一发现也得到了核磁共振和 X 射线晶体学的证实。使用钯催化的 Heck 反应，也将过苯甲酰化的 C-烯丙基甘露糖苷转化为 1,1'-联苯类似物。两个产生的次要反应产物与尿路致病性大肠杆菌FimH 共结晶。或者，主要的和预期的 Heck 产品的 KD 处于低 nM 范围内，如 SPR 所测量的。
• The Reaction of Ammonia with some Acetylated and Benzoylated Monosaccharides. III. Derivatives of D-Galactose
  作者：Jorge O. Deferrari、Venancio Deulofeu

  DOI：10.1021/jo50008a005

  日期：1952.8