2-C-hydroxymethyl-2,3-O-isopropylidene-5-O-trityl-α,β-D-ribofuranose | 114474-98-5

• 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: 2-C-hydroxymethyl-2,3-O-isopropylidene-5-O-trityl-α,β-D-ribofuranose
• 英文别名: 2-C-(hydroxymethyl)-2,3-O-(isopropylidene)-5-O-(triphenylmethyl)-D-ribofuranose；(3aR,6R,6aR)-3a-(hydroxymethyl)-2,2-dimethyl-6-(trityloxymethyl)-6,6a-dihydro-4H-furo[3,4-d][1,3]dioxol-4-ol
• CAS: 114474-98-5；114474-99-6
• 化学式: C₂₈H₃₀O₆
• 分子量: 462.543
• InChiKey: KQQHSFNAQLVAMC-OVHROIHKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  2-C-hydroxymethyl-2,3-O-isopropylidene-5-O-trityl-α,β-D-ribofuranose 在 4-二甲氨基吡啶 咪唑 、 甲酸 、 乙醚 、 碘 、 sodium hydride 、 三苯基膦 、 锌 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 为溶剂， 反应 26.0h， 生成 (4R,5R)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde
  参考文献：
  名称：

  Stereoselective synthesis of (−)- and (+)-pentenomycins using RCM

  摘要：

  An efficient synthesis of enantiopure (-)- and (+)-pentenomycins are described by reductive iodo elimination and ring-closing metathesis (RCM), as the key steps. The first synthesis of the unnatural (+)-isomer is described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01132-8
• 作为产物：
  描述：

  2,3-异亚丙氧基-D-呋喃核糖苷 在 4-二甲氨基吡啶 potassium carbonate 、 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 20.0h， 生成 2-C-hydroxymethyl-2,3-O-isopropylidene-5-O-trityl-α,β-D-ribofuranose
  参考文献：
  名称：

  Stereoselective synthesis of (−)- and (+)-pentenomycins using RCM

  摘要：

  An efficient synthesis of enantiopure (-)- and (+)-pentenomycins are described by reductive iodo elimination and ring-closing metathesis (RCM), as the key steps. The first synthesis of the unnatural (+)-isomer is described. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(03)01132-8

文献信息

• New syntheses of 2′-C-methylnucleosides starting from d-glucose and d-ribose
  作者：Leon N. Beigelman、Boris S. Ermolinsky、Galina V. Gurskaya、Elena N. Tsapkina、Marat Ya. Karpeisky、Sergey N. Mikhailov

  DOI：10.1016/0008-6215(87)80059-9

  日期：1987.9

  developed for the synthesis of 2′-C-methylnucleosides starting from d -glucose and d -ribose. 3-O-benzyl-1,2-O-isopropylidene-3-C-methyl-α- d -allofuranose was prepared in 5 steps from d -glucose and converted into 1,2,3-tri-O-acetyl-2-C-methyl-5-O-p-methylbenzoyl- d -ribofuranose (5), the starting compound for nucleoside synthesis. Compound 5 was also synthesised from 2-C-hydroxymethyl-2,3-O-isopr

  摘要已经开发了从d-葡萄糖和d-核糖开始合成2'-C-甲基核苷的有效通用方法。从d-葡萄糖经5个步骤制备3-O-苄基-1,2-O-异亚丙基-3-C-甲基-α-d-呋喃糖，并将其转化为1,2,3-三-O-乙酰基-2 -C-甲基-5-Op-甲基苯甲酰基-d-核呋喃糖（5），核苷合成的起始化合物。化合物5也由2-C-羟甲基-2,3-O-异亚丙基-5-O-三苯甲基-d-呋喃呋喃糖合成，其由d-核糖经3步制备。在F3CSO3OSiMe3存在下，将5与尿嘧啶，N4-苯甲酰基胞嘧啶和N6-苯甲酰腺嘌呤的双三甲基甲硅烷基衍生物缩合，然后除去保护性酰基，得到相应的2'-C-甲基核苷。
• Synthesis of 2′-C-methyl-branched isonucleosides
  作者：Tony Bouisset、Gilles Gosselin、Ludovic Griffe、Jean-Christophe Meillon、Richard Storer

  DOI：10.1016/j.tet.2008.05.022

  日期：2008.7

  Novel regioisomers of 2'-methyl-branched nucleosides were designed and synthesized to mimic potent anti-viral drugs like Valopicitabine. The short and efficient synthesis of the targets involves a one-pot tosylation/cyclization step that leads to an activated furan scaffold on which the isonucleosides were built. (C) 2008 Elsevier Ltd. All rights reserved.
• BEIGELMAN, LEON N.;ERMOLINSKY, BORIS S.;GURSKAYA, GALINA V.;TSAPKINA, ELE+, CARBOHYDR. RES., 166,(1987) N 2, 219-232
  作者：BEIGELMAN, LEON N.、ERMOLINSKY, BORIS S.、GURSKAYA, GALINA V.、TSAPKINA, ELE+

  DOI：——

  日期：——
• BEIGELMAN, LEON N.;ERMOLINSKY, BORIS S.;GURSKAYA, GALYNA V.;TSAPKINA, ELE+, 7TH SYMP. CHEM. NUCL. ACID COMPON., BECHYNE CASTLE, AUG. 30TH - SEPT. 5TH+
  作者：BEIGELMAN, LEON N.、ERMOLINSKY, BORIS S.、GURSKAYA, GALYNA V.、TSAPKINA, ELE+

  DOI：——

  日期：——
• Stereoselective synthesis of (−)- and (+)-pentenomycins using RCM
  作者：G. Venkata Ramana、B. Venkateswara Rao

  DOI：10.1016/s0040-4039(03)01132-8

  日期：2003.6

  An efficient synthesis of enantiopure (-)- and (+)-pentenomycins are described by reductive iodo elimination and ring-closing metathesis (RCM), as the key steps. The first synthesis of the unnatural (+)-isomer is described. (C) 2003 Elsevier Science Ltd. All rights reserved.