5β-vinyl-4β-tosyl-2α,3α-O-isopropylidene tetrahydrofuran | 43138-33-6

• 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: 5β-vinyl-4β-tosyl-2α,3α-O-isopropylidene tetrahydrofuran
• 英文别名: 1,2-O-isopropylidene-3-O-tosyl-5,6-dideoxy-α-D-xylo-hex-5-enofuranose；[(3aR,5R,6S,6aR)-5-ethenyl-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] 4-methylbenzenesulfonate
• CAS: 43138-33-6
• 化学式: C₁₆H₂₀O₆S
• 分子量: 340.397
• InChiKey: LHUHOYACGJQVAP-LXTVHRRPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  79.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5β-vinyl-4β-tosyl-2α,3α-O-isopropylidene tetrahydrofuran 在 吡啶 、 三氟甲磺酸三甲基硅酯 、 dimethyl sulfide borane 、 potassium tert-butylate 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 119.0h， 生成 6'-O-benzoyl-2'-deoxy-2'-(adenine-9-yl)-5'-deoxy-1',4'-anhydro-D-altritol
  参考文献：
  名称：

  Novel isonucleoside analogues: synthesis of 2′-deoxy-2′-nucleobase-5′-deoxy-1′,4′-anhydro-d-altritol

  摘要：

  A new class of isonucleoside analogues with branched-sugar 2'-deoxy-2'-nucleobase-5'-deoxy-1',4'-anhydro-D-altritol (21, 23a-c) has been synthesized from D-glucose in Il steps. The construction of branched-chain sugars has been carried out by hydroboration-oxidation of a double bond in the corresponding hexose. The key intermediate 12 was synthesized from the branched-chain sugar 11 by the reductive cleavage reaction in the presence of TMSOTf and triethylsilane. A strong solvent effect was observed in the intramolecular nucleophilic substitution of 12. The protic solvent is favorable to form the bicyclic compound 18 by double S(N)2 substitution. The opening reaction of epoxide 17 by nucleobases was achieved regioselectively to give the desired isonucleosides in reasonable yield. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(00)00136-1
• 作为产物：
  描述：

  1,2-O-异亚丙基-D-呋喃葡萄糖 在 吡啶 、 六正丁基二锡 、 二正丁基氧化锡 作用下， 以 苯 为溶剂， 反应 8.0h， 生成 5β-vinyl-4β-tosyl-2α,3α-O-isopropylidene tetrahydrofuran
  参考文献：
  名称：

  Tsuda, Yoshisuke; Sato, Yoshiyuki; Kanemitsu, Kimihiro, Chemical and Pharmaceutical Bulletin, 1996, vol. 44, # 8, p. 1465 - 1475

  摘要：

  DOI：

文献信息

• Synthesis of (1<i>R</i>, 2<i>R</i>, 4<i>S</i>, 5<i>R</i>)-2,4-Diyhdroxy-5-hydroxymethylcyclopentylamine and its Conversion to an Analogue of Aristeromycin
  作者：Atanu Roy、Ranjan Patra、Basudeb Achari、Sukhendu Mandal

  DOI：10.1055/s-1997-5795

  日期：1997.11

  Isoaristeromycin (1), an isomer of the nucleoside antibiotic aristeromycin, has been synthesized in twelve steps from D-glucose.

  Isoaristeromycin（1），是核苷抗生素aristeromycin的异构体，已通过12个步骤从D-葡萄糖合成。
• Singha; Tripathi; Roy, Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2001, vol. 40, # 10, p. 919 - 924
  作者：Singha、Tripathi、Roy、Achari、Mandal

  DOI：——

  日期：——
• Greening the Wacker process
  作者：Mukund G. Kulkarni、Yunnus B. Shaikh、Ajit S. Borhade、Sanjay W. Chavhan、Attrimuni P. Dhondge、Dnyaneshwar D. Gaikwad、Mayur P. Desai、Deekshaputra R. Birhade、Nagorao R. Dhatrak

  DOI：10.1016/j.tetlet.2013.01.082

  日期：2013.5

  Wacker oxidation of various terminal olefins with Pd-0/C-KBrO3, a nontoxic, environmentally benign, and easy to handle catalyst system, was achieved in high isolated yields. The described protocol offers an alternative to the traditional Wacker system which uses CuCl2 as co-catalyst. The catalyst is reusable while maintaining high activity and selectivity. (C) 2013 Elsevier Ltd. All rights reserved.