1-O-acetyl-2,3,4-tri-O-benzyl-6-deoxy-α-L-mannose | 80152-99-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-O-acetyl-2,3,4-tri-O-benzyl-6-deoxy-α-L-mannose
• 英文别名: 1-O-Acetyl-2,3,4-tri-O-benzyl-α-L-rhamnopyranose；[(2S,3R,4R,5S,6S)-6-methyl-3,4,5-tris(phenylmethoxy)oxan-2-yl] acetate
• CAS: 80152-99-4
• 化学式: C₂₉H₃₂O₆
• 分子量: 476.569
• InChiKey: OOQYKGWPDLNECP-XJQDHBRNSA-N

物化性质

• 沸点：
  576.6±50.0 °C(Predicted)
• 密度：
  1.19±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1-O-acetyl-2,3,4-tri-O-benzyl-6-deoxy-α-L-mannose 在 palladium on activated charcoal 、 Ag-silicate 3 A molecular sieve 、 氢溴酸 、 氢气 、 sodium methylate 作用下， 以 1,4-二氧六环 、 甲醇 、 二氯甲烷 为溶剂， 反应 5.07h， 生成 3-O-β-L-Rhamnopyranosyl-L-rhamnopyranose
  参考文献：
  名称：

  Paulsen, Hans; Kutschker, Wolfram; Lockhoff, Oswald, Chemische Berichte, 1981, vol. 114, # 10, p. 3233 - 3241

  摘要：

  DOI：
• 作为产物：
  描述：

  Benzyl-2,3,4-tri-O-benzyl-β-L-rhamnopyranosid 在 盐酸 作用下， 以 1,4-二氧六环 、 吡啶 为溶剂， 反应 42.0h， 生成 1-O-acetyl-2,3,4-tri-O-benzyl-6-deoxy-α-L-mannose
  参考文献：
  名称：

  Paulsen, Hans; Kutschker, Wolfram; Lockhoff, Oswald, Chemische Berichte, 1981, vol. 114, # 10, p. 3233 - 3241

  摘要：

  DOI：

文献信息

• Sc(OTf)₃as Efficient Catalyst for Aryl<i>C</i>-Glycoside Synthesis
  作者：Keisuke Suzuki、Akimi Ben、Takahito Yamauchi、Takashi Matsumoto

  DOI：10.1055/s-2003-44988

  日期：——

  s: Sc(OTf) 3 was found to be an efficient catalyst for the C-glycosylation of phenols. Reactions of various functionalized phenols and glycosyl acetates, including an azido-bearing one, are achieved by using a catalytic amount of Sc(OTf) 3 (10 mol % for neutral sugars or 50 mol% for an azido sugar) under mild conditions.

  s：Sc(OTf) 3 被发现是苯酚C-糖基化的有效催化剂。通过在温和条件下使用催化量的 Sc(OTf) 3 （中性糖为 10 mol% 或叠氮糖为 50 mol%），可以实现各种官能化酚和醋酸糖基乙酸酯的反应，包括含叠氮基的反应。
• The role of sugar configuration in the acetolysis of 6-deoxyhexose methyl glycosides
  作者：Luigi Cirillo、Annalida Di Nola、Emiliano Bedini、Michelangelo Parrilli

  DOI：10.1016/j.carres.2009.08.037

  日期：2009.11

  equiv ZnCl(2) in 2:1 v/v Ac(2)O-AcOH at 5 degrees C; 10:10:1 v/v/v Ac(2)O-AcOH-TFA at 70 degrees C) was studied. We focused on the effect of sugar configuration on the competition between mechanisms with activation at exocyclic or endocyclic oxygen site. No effect was detected in acetolysis using the TFA protocol promoting an exo-activation mechanism, which affords 1-O-Ac-pyranosides regardless of sugar

  在两个温和的条件下（5当量10：10：1 v / v Ac（2）O-AcOH; 10：10：1 v / v / v中的10个当量ZnCl（2）在两个温和的条件下乙酰化几个过苄基的6-脱氧己糖甲基糖苷研究了在70摄氏度下的Ac（2）O-AcOH-TFA）。我们专注于糖构型对环外或环内氧位点激活机制之间竞争的影响。使用TFA方案促进外泌激活机制的乙酰分解没有发现任何作用，该机制可提供1-O-Ac-吡喃糖苷，而与糖的构型无关。相反，它在确定ZnCl（2）促进的乙解中的内-外-产品分布上具有主要作用。
• A new, efficient method for hydrolysis of the anomeric acetyl group in substituted hexopyranoses
  作者：Anna Banaszek、Xavier Bordas Cornet、Aleksander Zamojski

  DOI：10.1016/s0008-6215(00)90683-9

  日期：1985.12
• First synthesis of astilbin, biologically active glycosyl flavonoid isolated from Chinese folk medicine
  作者：Ken Ohmori、Hiroki Ohrui、Keisuke Suzuki

  DOI：10.1016/s0040-4039(00)00826-1

  日期：2000.7

  A synthetic route to a biologically active glycosyl flavonoid, astilbin (1), was developed. The tetra-benzyl ether 4, derived from (+)-catechin, was glycosylated with the L-rhamnosyl donor 10 by using Cp2HfCl2AgClO4, and subsequent oxidation of the C(4) position of the flavan skeleton followed by deprotection gave 1. (C) 2000 Elsevier Science Ltd. All rights reserved.
• Cationic zirconocene- or hafnocene-based Lewis acids in organic synthesis: glycoside–flavonoid analogy
  作者：Ken Ohmori、Keisuke Hatakeyama、Hiroki Ohrui、Keisuke Suzuki

  DOI：10.1016/j.tet.2003.08.076

  日期：2004.2

  Cationic metallocene species, generated from Cp2MCl2 and AgClO4 (M=Zr, Hf), were used for the glycosylation of catechin derivative 2, enabling a concise synthesis of a glycosyl flavonoid, astilbin (1). Further study revealed the efficiency of this Lewis acidic species for S(N)1-type activation of the C(4) position of catechin derivative 11, enabling selective substitution with various nucleophiles. (C) 2003 Elsevier Ltd. All rights reserved.