1,2-anhydro-3,4-di-O-benzyl-6-O-trityl-α-D-glucopyranoside | 169824-26-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1,2-anhydro-3,4-di-O-benzyl-6-O-trityl-α-D-glucopyranoside
• 英文别名: (1S,3R,4R,5S,6R)-4,5-bis(phenylmethoxy)-3-(trityloxymethyl)-2,7-dioxabicyclo[4.1.0]heptane
• CAS: 169824-26-4
• 化学式: C₃₉H₃₆O₅
• 分子量: 584.712
• InChiKey: GQXYSLICPUYYHO-JTDOPDNRSA-N

物化性质

• 沸点：
  684.7±55.0 °C(Predicted)
• 密度：
  1.24±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.1
• 重原子数：
  44
• 可旋转键数：
  12
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  49.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-anhydro-3,4-di-O-benzyl-6-O-trityl-α-D-glucopyranoside 在 吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 硫酸 、 四丁基氯化铵 、 碳酸氢钠 、 对甲苯磺酸 、 三乙胺 、 sodium chloride 、 potassium bromide 、 zinc(II) chloride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 17.75h， 生成 (2S,3S,4S,5R,6R)-5-Acetoxy-3,4-bis-benzyloxy-6-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-2-carboxylic acid
  参考文献：
  名称：

  Synthesis and Biological Evaluation of a Backbone-Modified Phytoalexin Elicitor

  摘要：

  AbstractTwo suitably protected building blocks (11 and 33) for the preparation of amide‐linked heptaglucoside mimetic 2, an analogue of the naturally occurring phytoalexin elicitor 1a, were readily accessible by glycal chemistry. Sequential elongation of terminal glucuronide 21 with laminaribiosyl hemiaminal 33 and anomeric amine 11 by EDC/HOBt‐catalyzed condensation and two‐step conversion of the C6‐OTr moiety into the corresponding carboxylate function afforded homogeneous carbopeptoid 2 in high overall yield. It was found that replacement of the acetal linkages by the more rigid amide bonds destroys the phytoalexin‐elicitor activity.

  DOI：

  10.1002/chem.19970030614
• 作为产物：
  描述：

  3,4-di-O-benzyl-6-O-trityl-D-glucal 在 二甲基二环氧乙烷 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 0.08h， 以94%的产率得到1,2-anhydro-3,4-di-O-benzyl-6-O-trityl-α-D-glucopyranoside
  参考文献：
  名称：

  Timmers, Cornelis M.; Marel, Gijsbert A. van der; Boom, Jacques H. van, Chemistry - A European Journal, 1995, vol. 1, # 3, p. 161 - 164

  摘要：

  DOI：

文献信息

• Stereoselective Synthesis of α-C-(alkynyl)-glycosides via Ring-opening of α-1,2-Anhydrosugars
  作者：Michiel A Leeuwenburgh、Cornelis M Timmers、Gijsbert A van der Marel、Jacques H van Boom、Jean-Maurice Mallet、Pierre G Sinaÿ

  DOI：10.1016/s0040-4039(97)01381-6

  日期：1997.9

  Ring-opening of an α-1,2-epoxide function in sugars with lithium alkynyl derivatives in the presence of zinc chloride proceeds with retention of configuration to afford α-C-(alkynyl)-glycosides in reasonable yields. © 1997 Elsevier Science Ltd.

  在氯化锌的存在下，具有炔基锂衍生物的糖中的α-1,2-环氧官能团开环，保留了构型，从而以合理的收率得到了α- C-（炔基）-糖苷。©1997爱思唯尔科学有限公司。
• 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.
• Synthesis and Biological Evaluation of a Backbone-Modified Phytoalexin Elicitor
  作者：C. M. Timmers、J. J. Turner、C. M. Ward、G. A. van der Marel、M. L. C. E. Kouwijzer、P. D. J. Grootenhuis、J. H. van Boom

  DOI：10.1002/chem.19970030614

  日期：1997.6

  AbstractTwo suitably protected building blocks (11 and 33) for the preparation of amide‐linked heptaglucoside mimetic 2, an analogue of the naturally occurring phytoalexin elicitor 1a, were readily accessible by glycal chemistry. Sequential elongation of terminal glucuronide 21 with laminaribiosyl hemiaminal 33 and anomeric amine 11 by EDC/HOBt‐catalyzed condensation and two‐step conversion of the C6‐OTr moiety into the corresponding carboxylate function afforded homogeneous carbopeptoid 2 in high overall yield. It was found that replacement of the acetal linkages by the more rigid amide bonds destroys the phytoalexin‐elicitor activity.
• Timmers, Cornelis M.; Marel, Gijsbert A. van der; Boom, Jacques H. van, Chemistry - A European Journal, 1995, vol. 1, # 3, p. 161 - 164
  作者：Timmers, Cornelis M.、Marel, Gijsbert A. van der、Boom, Jacques H. van

  DOI：——

  日期：——