(3,4,6-tri-O-benzyl-α-D-glucopyranosyl)(phenyl)ethyne | 200621-39-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3,4,6-tri-O-benzyl-α-D-glucopyranosyl)(phenyl)ethyne
• 英文别名: (2R,3S,4R,5R,6R)-2-(2-phenylethynyl)-4,5-bis(phenylmethoxy)-6-(phenylmethoxymethyl)oxan-3-ol
• CAS: 200621-39-2
• 化学式: C₃₅H₃₄O₅
• 分子量: 534.652
• InChiKey: USDKLWMIFPQDFK-CKQPALCZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  40
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3,4,6-tri-O-benzyl-α-D-glucopyranosyl)(phenyl)ethyne 在 dicobalt octacarbonyl 、 三氟甲磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 3.0h， 以76%的产率得到(3,4,6-tri-O-benzyl-β-D-glucopyranosyl)(phenyl)ethyne
  参考文献：
  名称：

  A convenient route to cis- and trans-fused bicyclic ethers by ruthenium mediated ring-closing metathesis of diene and enyne carbohydrate derivatives

  摘要：

  A general approach towards the construction of highly functionalised pyranopyran and pyranofuran systems via Grubbs [Ru] catalysed ring-closing metatheses of neighbouring vinyl-O-allyl and vinyl-O-propargyl functions on monosaccharide scaffolds is described. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(99)00296-3
• 作为产物：
  描述：

  3,4,6-三苄氧基-D-葡萄烯糖 在 二甲基二环氧乙烷 、 zinc(II) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 5.5h， 生成 (3,4,6-tri-O-benzyl-α-D-glucopyranosyl)(phenyl)ethyne
  参考文献：
  名称：

  Zinc-Mediated Synthesis of α-C-Glycosides from 1,2-Anhydroglycosides

  摘要：

  α-C-糖苷是通过将有机锌试剂加入糖醇环氧化物制备的。在CF3COOH的存在下，二烷基和二芳基锌试剂能以53-82%的产率提供相应的α-糖苷。由RLi与氯化锌反应形成的有机锌氯化物RZnCl也可以成功应用于这种偶联反应，并具有很高的α-选择性。

  DOI：

  10.1055/s-2003-38751

文献信息

• A Novel Approach Towards <i>cis-</i> and <i>trans-</i>Fused Pyranopyrans Based on Ring-Closing Metathesis Reaction of Carbohydrate Derivatives
  作者：Michiel Leeuwenburgh、Herman Overkleeft、Gijsbert van der Marel、Jacques van Boom

  DOI：10.1055/s-1997-1009

  日期：1997.11

  A novel synthesis of both cis- and trans-fused pyranopyran systems, based on ring-closing metathesis of glycal derived dienes, is described. Isomerisation of the resulting allylic double bond provides a new cyclic enol ether, thus opening the way to an iterative synthesis of cis-(trans-)fused cyclic polyethers.

  本文介绍了一种基于甘醛衍生二烯的闭环偏析合成顺式和反式融合吡喃体系的新合成方法。由此产生的烯丙基双键的异构化提供了一种新的环状烯醇醚，从而为顺式（反式）融合环状聚醚的迭代合成开辟了道路。
• Stereoselective Synthesis of 1,2-Annulated Sugars Having Substituted Tetrahydropyran/(-furan) Scaffolds Using the Prins-Reaction
  作者：Ande Chennaiah、Sateesh Dubbu、Kadigachalam Parasuraman、Yashwant D. Vankar

  DOI：10.1002/ejoc.201801273

  日期：2018.12.19

  A novel and highly stereoselective method for the synthesis of 1,2‐annulated sugars having substituted tetrahydropyran and tetrahydrofuran moieties using the silyl‐Prins and alkyne‐Prins reactions is reported. The versatility of the present route has been demonstrated in the synthesis of cis‐sugar fused 4H‐naptho[1,2‐b]pyran and cis‐sugar fused pyrano[3,2‐c][1]benzopyran derivatives.

  报道了一种新颖的，高度立体选择性的方法，该方法使用甲硅烷基-Prins和炔烃-Prins反应合成具有取代的四氢吡喃和四氢呋喃部分的1,2-环糖。本路线的多功能性已在合成顺式-糖融合的4 H-萘[1,2- b ]吡喃和顺式-糖融合的吡喃并[3,2- c ] [1]苯并吡喃衍生物中得到证明。
• From <i>α</i>‐1,2‐Anhydrosugars to <i>C</i>‐Glycosides: The Influence of Lewis Acids and Nucleophiles on the Stereochemistry
  作者：Michiel A. Leeuwenburgh、Gijsbert A. van der Marel、Herman S. Overkleeft、Jacques H. van Boom

  DOI：10.1081/car-120026458

  日期：2003.12.31

  Ring opening of the epoxide function in alpha-1,2-anhydrosugars with alkynyl zinc and titanium compounds proceeds with retention of configuration to afford alpha-C-alkynylglycosides in reasonable to good yields, while the use of the corresponding alkynyltrifluoroborates results in the formation alpha/beta mixtures. Vinyl nucleophiles predominantly afford alpha-products, whereas allyl and allenyl species almost exclusively yield beta-C-glycosides.
• Zinc-Mediated Synthesis of α-<i>C</i>-Glycosides from 1,2-Anhydroglycosides
  作者：Song Xue、Kai-Zhen Han、Lin He、Qing-Xiang Guo

  DOI：10.1055/s-2003-38751

  日期：——

  α-C-Glycosides have been prepared by the addition of organozinc reagents to glycal epoxides. Dialkyl and diaryl zinc reagents in the presence of CF3COOH provide the corresponding α-glycosides in 53-82% yields. Organozinc chlorides RZnCl formed by the reaction RLi with zinc chloride can also be successfully applied to this coupling reaction with high α-selectivity.

  α-C-糖苷是通过将有机锌试剂加入糖醇环氧化物制备的。在CF3COOH的存在下，二烷基和二芳基锌试剂能以53-82%的产率提供相应的α-糖苷。由RLi与氯化锌反应形成的有机锌氯化物RZnCl也可以成功应用于这种偶联反应，并具有很高的α-选择性。
• A convenient route to cis- and trans-fused bicyclic ethers by ruthenium mediated ring-closing metathesis of diene and enyne carbohydrate derivatives
  作者：Michiel A. Leeuwenburgh、Camiel Kulker、Howard I. Duynstee、Herman S. Overkleeft、Gijsbert A. van der Marel、Jacques H. van Boom

  DOI：10.1016/s0040-4020(99)00296-3

  日期：1999.7

  A general approach towards the construction of highly functionalised pyranopyran and pyranofuran systems via Grubbs [Ru] catalysed ring-closing metatheses of neighbouring vinyl-O-allyl and vinyl-O-propargyl functions on monosaccharide scaffolds is described. (C) 1999 Elsevier Science Ltd. All rights reserved.