phenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside | 113019-35-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: phenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside
• 英文别名: phenyl 2,3-dideoxy-4,6-di-O-benzyl-α-D-erythro-hex-2-enopyranoside；phenyl 4,6-di-O-benzyl-2,3-dideoxy-α-D-erythro-hex-2-enopyranoside；(2R,3S,6R)-6-phenoxy-3-phenylmethoxy-2-(phenylmethoxymethyl)-3,6-dihydro-2H-pyran
• CAS: 113019-35-5
• 化学式: C₂₆H₂₆O₄
• 分子量: 402.49
• InChiKey: RZCPXTOWVSJJCF-NXCFDTQHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  phenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside 在 偶氮二异丁腈 、 三正丁基氢锡 、 1,4-双(二苯基膦)丁烷 、 bis(dibenzylideneacetone)-palladium⁽⁰⁾ 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 4.5h， 生成 ethyl 2-(4',6'-di-O-benzyl-2',3'-dideoxy-α-D-erythro-hex-2'-enopyranosyl)-2-(ethoxycarbonyl)acetate
  参考文献：
  名称：

  Palladium(0)-based approach to functionalized C-glycopyranosides

  摘要：

  DOI：

  10.1021/jo00269a026
• 作为产物：
  描述：

  Acetic acid (2R,3S,6R)-2-acetoxymethyl-6-phenoxy-3,6-dihydro-2H-pyran-3-yl ester 在 氢氧化钾 、 sodium methylate 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 14.75h， 生成 phenyl 4,6-di-O-benzyl-2,3-dideoxy-α,β-D-erythro-hex-2-enopyranoside
  参考文献：
  名称：

  Palladium(0)-based approach to functionalized C-glycopyranosides

  摘要：

  DOI：

  10.1021/jo00269a026

文献信息

• FeCl₃/C as an efficient catalyst for Ferrier rearrangement of 3,4,6-tri-<i>O</i>-Benzyl-D-glucal
  作者：Yuling Mei、Youxian Dong、Juan Li、Bo Zhang、Guosheng Sun、Jiafen Zhou、Wenshuai Si、Yiwen Han、Zhenliang Wu、Jianbo Zhang

  DOI：10.1080/07328303.2020.1788575

  日期：2020.7.23

  Abstract FeCl3/C was used as an efficient and convenient promoter for glycosylation through Ferrier-type rearrangement of 3,4,6-tri-O-benzyl-D-glucal, which is a relatively unreactive substrate for this type of reaction. The method was applicable to a wide range of alcohols, especially phenols. A series of 2,3-unsaturated-O-glucosides were prepared efficiently (47–92%) by this method under mild conditions

  摘要FeCl3 / C被用作通过3,4,6-tri-O-苄基-D-葡糖的Ferrier型重排进行糖基化的有效且方便的启动子，它是此类反应的相对反应性底物。该方法适用于多种醇，尤其是酚。通过该方法在温和的条件下，可以有效地制备一系列2，3-不饱和的O-葡萄糖苷（47-92％）。
• NaHSO4 supported on silica gel: an alternative catalyst for Ferrier rearrangement of glycals
  作者：Henok H. Kinfe、Fanuel M. Mebrahtu、Khuphukile Sithole

  DOI：10.1016/j.carres.2011.08.023

  日期：2011.11

  NaHSO(4) supported on silica gel catalyses the Ferrier rearrangement reaction of 3,4,6-tri-O-acetyl-D-glucal with alcohols and thiols to give the corresponding 2,3-unsaturated glycosides in high anomeric selectivity and good to excellent yield in short reaction time.

  载于硅胶上的NaHSO（4）催化3,4,6-tri-O-乙酰基-D-葡萄糖与醇和硫醇的Ferrier重排反应，得到相应的2,3-不饱和糖苷，其端基异构体选择性高，且对反应时间短，产率极高。
• Palladium (0)-based approach to heterocyclic N-glycosyl derivatives
  作者：Véronique Bolitt、Brahim Chaguir、Denis Sinou

  DOI：10.1016/s0040-4039(00)92220-2

  日期：1992.4

  2′, 3′-Unsaturated pyranoside nucleosides have been prepared with high stereoselectivity and good yields, by a simple condensation procedure, involving palladium(0)-catalysis

  2'，3'-不饱和吡喃糖苷核苷已通过涉及钯（0）-催化的简单缩合程序以高立体选择性和高收率制备
• Y(OTf)3 as a highly efficient catalyst in Ferrier Rearrangement for the synthesis of O- and S-2,3-unsaturated glycopyranosides
  作者：Peiran Chen、Shan Li

  DOI：10.1016/j.tetlet.2014.08.092

  日期：2014.10

  By using Y(OTf)(3) as the catalyst, a series of 2,3-unsaturated-glucosides have been synthesized from 3,4,6-tri-O-acetyl-D-glucal, 3,4-di-O-acetyl-L-rhamnal, and 3,4,6-tri-O-benzyl-D-glucal under mild reaction conditions in good yields with high anomeric selectivities. It was found that, in this reaction, 3,4,6-tri-O-benzyl-D-glucal behaved differently from the other two glucals when it was reacted with phenol, O-benzyl glucoside instead of O-phenyl glucoside formed as the sole product. An explanation is given for this phenomenon. (C) 2014 Elsevier Ltd. All rights reserved.
• BRAKTA, MOHAMED;LHOSTE, PAUL;SINOU, DENIS, J. ORG. CHEM., 54,(1989) N, C. 1890-1896
  作者：BRAKTA, MOHAMED、LHOSTE, PAUL、SINOU, DENIS

  DOI：——

  日期：——