Allyl 2,3,4,6-Tetra-O-acetyl-β-D-mannopyranoside | 119111-32-9

• 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: Allyl 2,3,4,6-Tetra-O-acetyl-β-D-mannopyranoside
• 英文别名: [(2R,3R,4S,5S,6R)-3,4,5-triacetyloxy-6-prop-2-enoxyoxan-2-yl]methyl acetate
• CAS: 119111-32-9
• 化学式: C₁₇H₂₄O₁₀
• 分子量: 388.372
• InChiKey: CRUHDGOVWKFJBM-UHDSXZAQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  27
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  10

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  2,3,4,6-O-四乙酰基-D-吡喃甘露糖	2,3,4,6-tetra-O-acetyl-D-mannopyranose	140147-37-1	C14H20O10	348.307
  Α-D-五乙酸甘露糖酯	D-Mannose pentaacetate	25941-03-1	C16H22O11	390.344
  甘露糖	D-Mannose	530-26-7	C6H12O6	180.158

反应信息

• 作为反应物：
  描述：

  Allyl 2,3,4,6-Tetra-O-acetyl-β-D-mannopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 以100%的产率得到allyl β-D-mannopyranoside
  参考文献：
  名称：

  Synthesis of allyl 2-O-(α-l-arabinofuranosyl)-6-O-(α-d-mannopyranosyl)-β-d-mannopyranoside, a unique plant N-glycan motif containing arabinose

  摘要：

  The synthesis of the trisaccharide allyl 2-O-(alpha -L-arabinofuranosyl)-6-O-(alpha -D-mannopyranosyl)-beta -D-mannopyranoside is reported. Stereoselective glycosylation at C-6 of a non-protected allyl beta -mannoside with the acetylated alpha -D-mannosyl bromide gave the alpha-(1 --> 6)-disaccharide as the main product and the crystalline 3,6-branched trisaccharide as minor compound. Further glycosylation of the 2,3 diol (1 --> 6) disaccharide with L-arabinofuranosyl bromide furnished a mixture of 3-O- and 2-O-alpha -L-Ara-trisaccharides from which the title compound was isolated. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(00)00185-3
• 作为产物：
  描述：

  甘露糖 在 吡啶 、 sodium hydride 作用下， 以 various solvent(s) 为溶剂， 反应 12.0h， 生成 Allyl 2,3,4,6-Tetra-O-acetyl-β-D-mannopyranoside
  参考文献：
  名称：

  Klotz, Wolfgang; Schmidt, Richard R., Liebigs Annalen der Chemie, 1993, # 6, p. 683 - 690

  摘要：

  DOI：

文献信息

• Synthesis of Benzaldehyde-Functionalized Glycans: A Novel Approach Towards Glyco-SAMs as a Tool for Surface Plasmon Resonance Studies
  作者：Sebastian Kopitzki、Knud J. Jensen、Joachim Thiem

  DOI：10.1002/chem.200902693

  日期：——

  In recent years the interest in tools for investigating carbohydrate–protein (CPI) and carbohydrate‐carbohydrate interactions (CCI) has increased significantly. For the investigation of CPI and CCI, several techniques employing different linking methods are available. Surface plasmon resonance (SPR) imaging is a most appropriate tool for analyzing the formation of self‐assembled monolayers (SAM) of

  近年来，人们对研究碳水化合物-蛋白质（CPI）和碳水化合物-碳水化合物相互作用（CCI）的工具的兴趣大大增加。为了调查CPI和CCI，可以使用几种采用不同链接方法的技术。表面等离振子共振（SPR）成像是分析碳水化合物衍生物可模仿糖萼的自组装单分子膜（SAM）形成的最合适工具。与先前用于分析CPI和CCI的SPR成像方法相反，本文报道的新颖方法可轻松，快速地合成接头间隔子和碳水化合物衍生物，并通过控制配体的数量和方向来增强结合作用。为了通过还原胺化固定在具有生物排斥性的氨基官能化SPR芯片上，已通过包括烯烃复分解在内的几个简便步骤合成了多种醛官能化的聚糖结构（葡萄糖，半乳糖，甘露糖，葡糖胺，纤维二糖，乳糖和乳糖胺）。提出了针对凝集素伴刀豆球蛋白A的有效固定方法和首次结合研究。
• BiBr₃-Promoted Activation of Peracetylated Glycosyl Iodides: Straightforward Access to Synthetically Useful 2-<i>O</i>-Deprotected Allyl Glycosides
  作者：Antonello Pastore、Matteo Adinolfi、Alfonso Iadonisi

  DOI：10.1002/ejoc.200800914

  日期：2008.12

  anomeric activation of acetylated glycosyl iodides. This reactivity can be exploited for straightforward access to allyl glycosides unprotected at the O-2 position. The reported protocol appears to be convenient in comparison with the pre-existing ones in that shorter experimental times are needed and the use of strong acids is avoided. Suitable structural features of substrates (6-deoxy sugars or use

  亚化学计量量的 BiBr3 能够促进乙酰化糖基碘的异头活化。这种反应性可用于直接获得在 O-2 位置未受保护的烯丙基糖苷。与先前存在的协议相比，报告的协议似乎很方便，因为需要更短的实验时间并且避免使用强酸。底物的合适结构特征（6-脱氧糖或使用苯甲酰基或甲氧基羰基 2-O 参与基团）将过程切换到优先糖苷化，而不会在 O-2 位置脱保护。（© Wiley-VCH Verlag GmbH & Co. KGaA , 69451 德国魏因海姆, 2008)
• A Practical Synthetic Method for a- and b-Glycosyloxyacetic Acids
  作者：Tadakatsu Mandai、Hiroshi Okumoto、Tetsuta Oshitari、Katsuyoshi Nakanishi、Katsuhiko Mikuni、Ko-ji Hara、Ko-zo Hara

  DOI：10.3987/com-99-s43

  日期：——

  Dihydroxylation of allyl 2,3,4-tri-O-benzyl-6-O-tritylglycosides provides diols, the anomers of which can easily be separated by column chromatography in a practical scale. These anomers can be cleanly transformed into alpha- and beta-glycosyloxyacetic acids, respectively, via oxidative cleavage of the diol followed by oxidation.
• Klotz, Wolfgang; Schmidt, Richard R., Liebigs Annalen der Chemie, 1993, # 6, p. 683 - 690
  作者：Klotz, Wolfgang、Schmidt, Richard R.

  DOI：——

  日期：——
• Synthesis of allyl 2-O-(α-l-arabinofuranosyl)-6-O-(α-d-mannopyranosyl)-β-d-mannopyranoside, a unique plant N-glycan motif containing arabinose
  作者：Jean-Pierre Utille、Bernard Priem

  DOI：10.1016/s0008-6215(00)00185-3

  日期：2000.11

  The synthesis of the trisaccharide allyl 2-O-(alpha -L-arabinofuranosyl)-6-O-(alpha -D-mannopyranosyl)-beta -D-mannopyranoside is reported. Stereoselective glycosylation at C-6 of a non-protected allyl beta -mannoside with the acetylated alpha -D-mannosyl bromide gave the alpha-(1 --> 6)-disaccharide as the main product and the crystalline 3,6-branched trisaccharide as minor compound. Further glycosylation of the 2,3 diol (1 --> 6) disaccharide with L-arabinofuranosyl bromide furnished a mixture of 3-O- and 2-O-alpha -L-Ara-trisaccharides from which the title compound was isolated. (C) 2000 Elsevier Science Ltd. All rights reserved.