2,3,4-tri-O-benzyl-D-xylose diethyl dithioacetal | 108713-90-2

• 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: 2,3,4-tri-O-benzyl-D-xylose diethyl dithioacetal
• 英文别名: (2R,3S,4R)-5,5-bis(ethylsulfanyl)-2,3,4-tris(phenylmethoxy)pentan-1-ol
• CAS: 108713-90-2
• 化学式: C₃₀H₃₈O₄S₂
• 分子量: 526.761
• InChiKey: XPTMFTIQZJYCNX-SSBOKUKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  36
• 可旋转键数：
  17
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  98.5
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2,3,4-tri-O-benzyl-D-xylose diethyl dithioacetal 在 无水碳酸镉 、 pyridinium chlorochromate 、 mercury dichloride 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3S,4R,5E)-2,3,4-tribenzyloxyocta-5,7-diene-1-al
  参考文献：
  名称：

  Complete stereoselectivity in the intramolecular diels-alder reactionof a triene derivative from d-xylose

  摘要：

  DOI：

  10.1016/s0040-4039(00)80127-6
• 作为产物：
  描述：

  2,3,4-tri-O-benzyl-D-xylopyranose 生成 2,3,4-tri-O-benzyl-D-xylose diethyl dithioacetal
  参考文献：
  名称：

  HERCZEGH, PAL;ZSELY, MARTINA;SZILAGYI, LASZLO;BOGNAR, REZSO, TETRAHEDRON LETT., 29,(1988) N 4, 481-484

  摘要：

  DOI：

文献信息

• Intramolecular reactions of compounds derived from sugars. Part II.1 Stereo-controlled intramolecular diels-alder cyclizations of 16(E,Z),8-nonatrienes and 1-AZA-6(E,Z),8-nonatrienes
  作者：Pál Herczegh、Martina Zsély、László Szilágyi、Gyula Batta、István Bajza、Rezső Bognár

  DOI：10.1016/s0040-4020(01)80109-5

  日期：1989.1

  Intramolecular Diels-Alder reactions of E,Z mixtures of nonatrienes 6 and 9 led to the exclusive formation of the bicyclic compounds 10 and 11 respectively.

  壬基6和9的E，Z混合物的分子内Diels-Alder反应分别导致双环化合物10和11的排他性形成。
• Stereoselective Synthesis and Absolute Configuration of the C1′−C25′ Fragment of Symbiodinolide
  作者：Hiroyoshi Takamura、Takeshi Murata、Takahiro Asai、Isao Kadota、Daisuke Uemura

  DOI：10.1021/jo901162v

  日期：2009.9.4

  Stereoselective synthesis of the C1′−C25′ fragment of symbiodinolide, which was obtained as a degraded product from symbiodinolide by alkaline hydrolysis, has been accomplished. The synthetic route features Kotsuki coupling and Julia−Kocienski olefination in the introduction of the side chains. This enantio- and stereoselective synthesis has established the absolute configuration of the C1′−C25′ fragment.

  已经完成了共生双杀菌素的C1'-C25'片段的立体选择性合成，该共生双杀菌素是通过碱水解从共生双杀菌素的降解产物中获得的。在侧链的引入中，合成路线的特征是Kotsuki偶联和Julia-Kocienski烯烃化。该对映和立体选择性合成已经建立了C1'-C25'片段的绝对构型。
• Preparation of 5-Selenopentopyranose Sugars from Pentose Starting Materials by Samarium(II) Iodide or (Phenylseleno)formate Mediated Ring Closures
  作者：Mathew A. Lucas、Oanh T.K. Nguyen、Carl H. Schiesser、Shi-Long Zheng

  DOI：10.1016/s0040-4020(00)00299-4

  日期：2000.6

  4-tri-O-benzyl-5-benzylseleno-d-arabit-1-yl formate (13, 21, 22) in transformations which involve intramolecular nucleophilic attack of the benzylseleno moiety with concomitant loss of carbon dioxide and phenylselenoate. In a complementary procedure, treatment of 2,3,4-tri-O-benzyl-5-benzylseleno-5-deoxyribose (19) with samarium(II) iodide in THF affords 2,3,4-tri-O-benzyl-5-deoxy-5-seleno-d-ribopyranose

  2,3,4-三- ø -苄基-1,5-二去氧-5-硒代d-pentopyranose糖（16，23，24）很容易通过热制备的2,3,4-三ø -苄基-5--5-苄基硒代-d-ribit-1-基甲酸，2,3,4-三-O-苄基-5-苄基硒代-d-xylit-1-基甲酸根和2,3,4-三-O-苄基-5- benzylseleno-d-arabit -1-基甲酸盐（13，21，22），其中涉及benzylseleno部分与二氧化碳和phenylselenoate的同时损失分子内亲核进攻变换。在补充程序中，处理2,3,4-三-O-苄基-5-苄基硒基-5-脱氧核糖（19）在THF中用碘化sa（II）提供50％分离产率的2,3,4-三-O-苄基-5-脱氧-5-硒代-d-核吡喃糖（26），该过程最有可能涉及分子内均溶硒糖中硒原子上的取代。
• A route to several stereoisomers of castanospermine
  作者：Kevin Burgess、David A. Chaplin、Ian Henderson、Y. T. Pan、Alan D. Elbein

  DOI：10.1021/jo00030a014

  日期：1992.2

  The following three stereoisomers of castanospermine have been prepared: (1R,6R,7R,8S,8aR)-1,6,7,8-tetrahydroxyindolizidine (1), (1R,6S,7S,8S,8aR)-1,6,7,8-tetrahydroxyindolizidine (2), and (1R,6R,7S,8S,8aR)-1,6,7,8-tetrahydroxyindolizidine (3). Each of these compounds was synthesized via asymmetric allylation of pentose derivatives with [(Z)-gamma-(methoxymethoxy)allyl]diisopinocampheylborane, an approach which is, in principle, suitable for preparations of a total of eight stereoisomers of castanospermine. Compounds 1-3 were tested as possible inhibitors of various glycosidase enzymes and for anti-HIV-1 activity in cell cultures. They are very poor inhibitors of glycosidase enzymes; however, preliminary tests indicate indolizidines 1 and 3 have weak but significant anti-HIV activities.
• Samarium(II) iodide mediated intramolecular homolytic substitution at selenium: Preparation of 5-seleno-D-pentopyranose sugars from common pentose starting materials
  作者：Carl H. Schiesser、Shi-Long Zheng

  DOI：10.1016/s0040-4039(99)00990-9

  日期：1999.7

  Treatment of 2,3,4-tri-O-benzyl-5-benzylseleno-5-deoxyribose (9) with samarium(II) iodide in II-TF affords 2.3,4-tri-O-benzyl-5-deoxy-5-seleno-D-ribopyranose (10) in 50% isolated yield in a process most likely involving intramolecular homolytic substitution at the selenium atom. In a similar fashion, 2,3,4-tri-O-benzyl-5-deoxy-5-seleno-D-xylopyranose (16) and 2,3,4-tri-O-benzyl-5-deoxy-5-seleno-D-arabanopyranose (17) were prepared from analogous precursors in 21 and 12% yields respectively. (C) 1999 Elsevier Science Ltd. All rights reserved.