(1S,3R,6R,8S,9R,10R)-8-allyl-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane-9,10-diol | 498554-20-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1S,3R,6R,8S,9R,10R)-8-allyl-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane-9,10-diol
• 英文别名: (2R,4aR,6S,7R,8R,8aS)-2-phenyl-6-prop-2-enyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine-7,8-diol
• CAS: 498554-20-4
• 化学式: C₁₆H₂₀O₅
• 分子量: 292.332
• InChiKey: RNBMWCJHHYIEIG-LFTMDZKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  68.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,3R,6R,8S,9R,10R)-8-allyl-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane-9,10-diol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 2,6-二甲基吡啶 、 盐酸 、 4-二甲氨基吡啶 、 9-borabicyclo[3.3.1]nonane dimer 、 titanocene dichloride 、 四丁基氟化铵 、 四丁基碘化铵 、 sodium hydride 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 185.33h， 生成 {(1S,3Z,5R,7R,8S,9S,10R)-8-benzyloxy-9-(4-bromobenzyloxy)-5-(4-bromobenzyloxymethyl)-6,11-dioxabicyclo[5.4.0]undec-3-en-10-yl}methyl trifluoromethanesulfonate
  参考文献：
  名称：

  Synthesis of the AB-ring segment for the convergent construction of the left half in ciguatoxin

  摘要：

  The synthesis of the AB-ring segment aiming at the convergent construction of the left half in ciguatoxin (CTX1B) has been achieved by a strategy based on ring-closing metathesis (RCM) and diastereocontrolled hydroboration to cyclic vinyl ethers. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(02)01329-7
• 作为产物：
  描述：

  Acetic acid (2R,3R,4R,5S,6S)-3,5-diacetoxy-2-acetoxymethyl-6-allyl-tetrahydro-pyran-4-yl ester 在 camphor-10-sulfonic acid 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 、 乙腈 为溶剂， 反应 43.0h， 生成 (1S,3R,6R,8S,9R,10R)-8-allyl-3-phenyl-2,4,7-trioxabicyclo[4.4.0]decane-9,10-diol
  参考文献：
  名称：

  Synthesis and screening of bicyclic carbohydrate-based compounds: A novel type of antivirals

  摘要：

  A small library of bicyclic carbohydrate derivatives was synthesized and screened. A strong and selective activity against cytomegalovirus was found. Structure-activity relationship for this new type of antivirals is discussed. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2005.12.048

文献信息

• Studies on the Stereoselective Synthesis of <i>C</i>-Allyl Glycosides
  作者：Glenn J. McGarvey、Christopher A. LeClair、Bahar A. Schmidtmann

  DOI：10.1021/ol801710s

  日期：2008.11.6

  An investigation was carried out to explore the use of sulfoxide donors as common precursors to stereoisomeric C-glycoconjugates of glycoprotein and glycolipid tumor antigens. A study focusing on the effects of reaction conditions and substrate structure on the stereoselectivity of allylation was carried out. Although conditions were realized to selectively afford alpha-allylation products in good to excellent yields, the search for conditions favoring beta-selectivity proved less successful.
• Synthesis of the AB-ring segment for the convergent construction of the left half in ciguatoxin
  作者：Hideki Tanaka、Kentaro Kawai、Kenshu Fujiwara、Akio Murai

  DOI：10.1016/s0040-4020(02)01329-7

  日期：2002.12

  The synthesis of the AB-ring segment aiming at the convergent construction of the left half in ciguatoxin (CTX1B) has been achieved by a strategy based on ring-closing metathesis (RCM) and diastereocontrolled hydroboration to cyclic vinyl ethers. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis and screening of bicyclic carbohydrate-based compounds: A novel type of antivirals
  作者：Steven Van Hoof、Bart Ruttens、Idzi Hubrecht、Gert Smans、Petra Blom、Benedikt Sas、Johan Van hemel、Jan Vandenkerckhove、Johan Van der Eycken

  DOI：10.1016/j.bmcl.2005.12.048

  日期：2006.3

  A small library of bicyclic carbohydrate derivatives was synthesized and screened. A strong and selective activity against cytomegalovirus was found. Structure-activity relationship for this new type of antivirals is discussed. (C) 2005 Elsevier Ltd. All rights reserved.