4-penten-1-yl 2-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranoside | 143706-45-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 4-penten-1-yl 2-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranoside
• 英文别名: 4-pentenyl-2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside；Pentenyl 2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranoside；[(2S,3S,4S,5R,6R)-2-pent-4-enoxy-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-yl] acetate
• CAS: 143706-45-0
• 化学式: C₃₄H₄₀O₇
• 分子量: 560.687
• InChiKey: IQQXSPPFSYETFE-ZOHVZMGWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  41
• 可旋转键数：
  17
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  72.4
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  4-penten-1-yl 2-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranoside 在 N-碘代丁二酰亚胺 、 三乙基硅基三氟甲磺酸酯 、 碳酸氢钠 、 硫脲 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 生成 Dibromopentanyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-2,4-di-O-benzyl-α-D-mannopyranoside
  参考文献：
  名称：

  n-Pentenyl glycoside methodology for rapid assembly of homoglycans exemplified with the nonasaccharide component of a high-mannose glycoprotein

  摘要：

  DOI：

  10.1021/ja00047a080
• 作为产物：
  描述：

  4-戊烯-1-醇 在 氢氧化钾 、 三氟甲磺酸三甲基硅酯 、 四丁基溴化铵 作用下， 以 四氢呋喃 、 2,4,6-三甲基吡啶 、 二氯甲烷 为溶剂， 反应 2.0h， 生成 4-penten-1-yl 2-O-acetyl-2,3,6-tri-O-benzyl-α-D-glucopyranoside
  参考文献：
  名称：

  Intramolecular C-glycosylation of 2-O-benzylated pentenyl mannopyranosides: remarkable 1,2-trans stereoselectivity

  摘要：

  The IDCP-promoted intramolecular C-glycosylation of pentenyl alpha-mannopyranosides carrying, at O-2, an activated benzyl group gave, unexpectedly, the 1,2-trans-fused bicyclic product which corresponds to an alpha-C-aryl mannopyranose derivative. This remarkable, strained C-glycosyl compound was rapidly epimerized to the more stable 1,2-cis product on treatment with BF3.Et2O. The IDCP-reaction product could be elaborated into a 2-(alpha-C-mannopyranosyl)-3,4,5-trimethoxybenzyl alcohol derivative. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2003.10.006

文献信息

• Au^III-Halide/Phenylacetylene-Cata­lysed Glycosylations Using 1-<i>O</i>-Acetyl­furanoses and Pyranose 1,2-Ortho­esters as Glycosyl Donors
  作者：Asadulla Mallick、Yakkala Mallikharjunarao、Parasuraman Rajasekaran、Rashmi Roy、Yashwant D. Vankar

  DOI：10.1002/ejoc.201501245

  日期：2016.1

  1-O-Acetylfuranoses and pyranose 1,2-orthoesters were activated with an AuIII halide/phenylacetylene relay catalyst system, and they acted as excellent glycosyl donors. Thus, 1-O-acetyl-D-ribofuranose, 1-O-acetyl-D-lyxofuranose, and 1,2-orthoesters selectively gave the corresponding 1,2-trans glycosides, whereas 1-O-acetyl-D-arabinofuranose and 1-O-acetyl-D-xylofuranose both gave mixtures of 1,2-trans

  1-O-乙酰呋喃糖和吡喃糖 1,2-原酸酯用 AuIII 卤化物/苯乙炔中继催化剂系统活化，它们是优良的糖基供体。因此，1-O-乙酰基-D-呋喃核糖、1-O-乙酰基-D-lyxofuranose 和 1,2-原酸酯选择性地产生相应的 1,2-反式糖苷，而 1-O-乙酰基-D-阿拉伯呋喃糖和1-O-乙酰基-D-呋喃木糖均产生1,2-反式和1,2-顺式糖苷的混合物，其中以1,2-反式糖苷为主。
• Solid-Phase Oligosaccharide Synthesis:  Preparation of Complex Structures Using a Novel Linker and Different Glycosylating Agents
  作者：Rodrigo B. Andrade、Obadiah J. Plante、Luis G. Melean、Peter H. Seeberger

  DOI：10.1021/ol991071+

  日期：1999.12.1

  [formula: see text] A beta-(1-->4)-linked trisaccharide was prepared in 53% yield on a polymer support using glycosyl phosphates and released by cross-metathesis of a novel linker to reveal the anomeric n-pentenyl glycoside. Heptasaccharide 33 was prepared in 9% yield in 14 steps.

  [公式：参见文本]使用糖基磷酸酯在聚合物载体上以53％的收率制备β-（1-> 4）连接的三糖，并通过新型连接子的复分解而释放，从而揭示异头正戊烯糖苷。通过14个步骤以9％的产率制备七糖33。
• <i>n</i>-Pentenyl Glycoside Methodology in the Stereoselective Construction of the Tetrasaccharyl Cap Portion of <i>Leishmania</i> Lipophosphoglycan
  作者：Ashok Arasappan、Bert Fraser-Reid

  DOI：10.1021/jo9520102

  日期：1996.1.1

  Efficient and high yielding stereoselective assembly of the tetrasaccharyl cap region of the lipophosphoglycan from the protozoan parasite Leishmania using the n-pentenyl glycoside protocol is described in this paper. Both convergent and linear syntheses lead to the protected tetrasaccharide 14; however, the convergent assembly is more efficient in terms of product recovery. Regioselective reductive cleavage of benzylidene acetal 4 with triethylsilane-trifluoroacetic acid system liberates the required C-4 OH in excellent yield, without affecting the resident chloroacetate functionality.
• n-Pentenyl Mannoside Precursors for Synthesis of the Nonamannan Component of High Mannose Glycoproteins
  作者：J. Robert Merritt、Elizabeth Naisang、Bert Fraser-Reid

  DOI：10.1021/jo00095a020

  日期：1994.8

  The high-mannose oligosaccharide 1 is present on the conserved V3 loop of the viral coat of HIV1 known as GP-120. The mannan portion of this molecule has been prepared by utilization of halogen-promoted n-pentenyl glycoside (NPG) coupling. Two advantageous properties of NPG's facilitated construction of 1, one being the ability to activate the donor, even when C2 esterified (i.e., ''disarmed''), with NIS/Et(3)SiOTf, under which all reactions are complete within the time required to take a TLC sample. The second advantage was the ''side-tracking'' strategy which allowed the pentenyl group of a glycosyl acceptor to be rendered temporarily inactive by conversion to the dibromide. After coupling, the ''side-tracked'' NPG could be reactivated by reductive elimination to serve as the glycosyl donor in a subsequent step. With the appropriately protected monosaccharide precursors in hand, the nonamannan could be assembled by a virtually iterative protocol involving deprotection-coupling- deprotection-coupling...etc. as the only synthetic manipulations.
• Methods for Debrominating 4,5-Dibromopentanyl Glycosides
  作者：J. Robert Merritt、John S. Debenham、Bert Fraser-Reid

  DOI：10.1080/07328309608005425

  日期：1996.1

  Debromination of 4,5-dibromopentanyl glycosides to (re)generate n-pentenyl glycosides has been accomplished using zinc, samarium(II) iodide, and sodium iodide, respectively. The choice of reagent is dependent upon the reactivity of the substrate, as well as the protecting groups thereon.