allyl 2,3-di-O-benzyl-α-D-galactopyranoside | 100605-69-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3-di-O-benzyl-α-D-galactopyranoside
• 英文别名: (2R,3S,4S,5R,6S)-2-(hydroxymethyl)-4,5-bis(phenylmethoxy)-6-prop-2-enoxyoxan-3-ol
• CAS: 100605-69-4
• 化学式: C₂₃H₂₈O₆
• 分子量: 400.472
• InChiKey: XPNQNMXIMFZLNP-YSFPZDHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  allyl 2,3-di-O-benzyl-α-D-galactopyranoside 在 lithium aluminium tetrahydride 作用下， 以 吡啶 、 乙醚 为溶剂， 反应 0.33h， 生成 Allyl-2,3-di-O-benzyl-6-desoxy-α-D-galactopyranosid
  参考文献：
  名称：

  In situ Activating Glycosylation of 6-Deoxysugars: Synthesis ofO-α-D-Fucosyl-(1→4)-O-α-D-fucosyl-(1→4)-O-α-D-quinovosyl-(1→4)-D-quinovose

  摘要：

  线性四糖α-D-岩藻吡喃糖基-(1→4)-α-D-岩藻吡喃糖基-(1→4)-α-D-奎诺吡喃糖基-(1→4)-D-奎诺吡喃糖，即海星（Asterias amurensis）中星皂苷A的糖簇，通过汇聚合成法被成功合成。我们采用了位点特异性活化的糖基化方法，使用1-羟基糖衍生物以及p-硝基苯磺酰氯、三氟甲磺酸银和三乙胺组成的一套糖基化系统及相关体系。

  DOI：

  10.1246/bcsj.73.967
• 作为产物：
  描述：

  D-吡喃葡萄糖 在 甲烷磺酸 、 sodium hydride 、 碳酸氢钠 、 对甲苯磺酸 作用下， 以 吡啶 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.7h， 生成 allyl 2,3-di-O-benzyl-α-D-galactopyranoside
  参考文献：
  名称：

  In situ Activating Glycosylation of 6-Deoxysugars: Synthesis ofO-α-D-Fucosyl-(1→4)-O-α-D-fucosyl-(1→4)-O-α-D-quinovosyl-(1→4)-D-quinovose

  摘要：

  线性四糖α-D-岩藻吡喃糖基-(1→4)-α-D-岩藻吡喃糖基-(1→4)-α-D-奎诺吡喃糖基-(1→4)-D-奎诺吡喃糖，即海星（Asterias amurensis）中星皂苷A的糖簇，通过汇聚合成法被成功合成。我们采用了位点特异性活化的糖基化方法，使用1-羟基糖衍生物以及p-硝基苯磺酰氯、三氟甲磺酸银和三乙胺组成的一套糖基化系统及相关体系。

  DOI：

  10.1246/bcsj.73.967

文献信息

• Thiem, Joachim; Duckstin, Viola; Prahst, Archibald, Liebigs Annalen der Chemie, 1987, p. 289 - 295
  作者：Thiem, Joachim、Duckstin, Viola、Prahst, Archibald、Matzke, Michael

  DOI：——

  日期：——
• Synthesis of oligosaccharide fragments of the rhamnogalacturonan of Nerium indicum
  作者：Yuyong Ma、Xin Cao、Biao Yu

  DOI：10.1016/j.carres.2013.05.008

  日期：2013.8

  Three trisaccharides, one pentasaccharide, and one heptasaccharide, namely alpha-D-GalA-(1 -> 2)-alpha-L-Rha(1 -> 4)-beta-D-GalA-OC3H7 (1), alpha-L-Rha-(1 -> 4)-alpha-D-GalA-(1 -> 4)-beta-D-GalA-OC3H7 (2), alpha-D-GalA-(1 -> 4)-alpha-D-GalA-(1 -> 2)-alpha-L-Rha-OC3H7 (3), alpha-D-GalA-(1 -> 2)-alpha-L-Rha-(1 -> 4)-alpha-D-GalA-(1 -> 2)-alpha-L-Rha-(1 -> 4)-beta-D-GalA-OC3H7 (4), and alpha-D-GalA-(1 -> 2)-alpha-L-Rha-(1 -> 4)-alpha-D-GalA-(1 -> 2)-alpha-L-Rha-(1 -> 4)-alpha-D-GalA-(1 -> 2)-alpha-L-Rha-(1 -> 4)-beta-D-GalA-OC3H7 (5), which are relevant to the fragments of the rhamnogalacturonan of Nerium indicum, were concisely synthesized. The syntheses feature highly stereoselective formation of the alpha-D-GalA-linkage with GalA N-phenyltrifluoroacetimidates as donors. (c) 2013 Elsevier Ltd. All rights reserved.
• Selective TEMPO‐Catalyzed Chemicals vs. Electrochemical Oxidation of Carbohydrate Derivatives
  作者：Maximilien Barbier、Tony Breton、Karine Servat、Eric Grand、Boniface Kokoh、José Kovensky

  DOI：10.1080/07328300600636819

  日期：2006.5.1

  TEMPO-catalyzed electrochemical oxidation of carbohydrate derivatives was performed and compared with chemical oxidation, which requires the use of co-oxidants. Allyl-protected derivatives could be readily oxidized by both methods. Electrochemical selectivE oxidation of primary positions has been adapted to unprotected mono- and oligosaccharides.
• In situ Activating Glycosylation of 6-Deoxysugars: Synthesis of<b><i>O</i></b>-<b><i>α</i></b>-<b>D</b>-Fucosyl-(1→4)-<b><i>O</i></b>-<b><i>α</i></b>-<b>D</b>-fucosyl-(1→4)-<b><i>O</i></b>-<b><i>α</i></b>-<b>D</b>-quinovosyl-(1→4)-<b>D</b>-quinovose
  作者：Shinkiti Koto、Ami Kusunoki、Motoko Hirooka

  DOI：10.1246/bcsj.73.967

  日期：2000.4

  The linear tetrasaccharide, α-D-fucopyranosyl-(1→4)-α-D-fucopyranosyl-(1→4)-α-D-quinovopyranosyl-(1→4)-D-quinovopyranose, the sugar cluster of asterosaponin A from the starfish, Asterias amurensis, was synthesized in a convergent manner. We employed an in situ activating glycosylation using 1-OH sugar derivatives and a system of p-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, and triethylamine as well as a related system.

  线性四糖α-D-岩藻吡喃糖基-(1→4)-α-D-岩藻吡喃糖基-(1→4)-α-D-奎诺吡喃糖基-(1→4)-D-奎诺吡喃糖，即海星（Asterias amurensis）中星皂苷A的糖簇，通过汇聚合成法被成功合成。我们采用了位点特异性活化的糖基化方法，使用1-羟基糖衍生物以及p-硝基苯磺酰氯、三氟甲磺酸银和三乙胺组成的一套糖基化系统及相关体系。