3,4-O-isopropylidene-1-O-triphenylmethyl-L-glycero-2-tetrulose | 119927-20-7

• 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: 3,4-O-isopropylidene-1-O-triphenylmethyl-L-glycero-2-tetrulose
• 英文别名: 1-[(4S)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-trityloxyethanone
• CAS: 119927-20-7
• 化学式: C₂₆H₂₆O₄
• 分子量: 402.49
• InChiKey: NSDVYHKHLVDLJR-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  30
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3,4-O-isopropylidene-1-O-triphenylmethyl-L-glycero-2-tetrulose 在 吡啶 、 三氟乙酸 、 三氟乙酸酐 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 (2R,3R)-3,4-O-isopropylidene-2-(N-benzyloxyamino)-2-n-butylbutane-1,3,4-triol
  参考文献：
  名称：

  有机锂试剂与受保护的赤藓糖肟反应的非对映选择性

  摘要：

  有机锂试剂的几个赤藓酮糖衍生的手性（的CN键的加成ë） -和（Ž）-ketoxime醚已被证明是在（的情况下高度非对映ë） -异构体。已经提出了螯合和非螯合的过渡态来合理化这些结果，并附加了计算方法的支持。

  DOI：

  10.1016/s0957-4166(98)00145-1
• 作为产物：
  描述：

  (2S,3S)-1,2-O-isopropylidene-1,2,3,4-tetrol 在 4-二甲氨基吡啶 、 重铬酸吡啶 、 3 A molecular sieve 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成 3,4-O-isopropylidene-1-O-triphenylmethyl-L-glycero-2-tetrulose
  参考文献：
  名称：

  Marco, Jose L., Journal of Chemical Research, Miniprint, 1988, # 9, p. 2013 - 2016

  摘要：

  DOI：

文献信息

• Synthesis of Conjugated γ- and δ-Lactones from Aldehydes and Ketones via a Vinylation/Allylation-Ring Closing Metathesis-Oxidation Sequence
  作者：Miguel Carda、Encarnación Castillo、Santiago Rodríguez、Santiago Uriel、J. Alberto Marco

  DOI：10.1055/s-1999-2897

  日期：——

  Nucleophilic C-vinylation or C-allylation of aldehydes and ketones followed by O-allylation of the obtained carbinols gave the corresponding allyl ethers. Ring-closing metathesis of the latter afforded cyclic ethers (dihydrofurans and dihydropyrans, respectively) which were then subjected to allylic oxidation to yield conjugated γ- and δ-lactones.

  通过对醛和酮进行亲核碳乙烯基化或碳烯丙基化反应，随后对所得卡宾醇进行氧烯丙基化，得到了相应的烯丙醚。后者经过环闭合易位反应，分别得到环醚（二氢呋喃和二氢吡喃），再经过烯丙位的氧化反应，分别生成共轭的γ-和δ-内酯。
• Diastereoselective Addition of Grignard Reagents to 3,4-<i>O</i>-Isopropylidene-1-<i>O</i>-triphenylmethyl-L-<i>glycero</i>-2-tetrulose and 1-<i>O</i>-Benzoyl-3,4-<i>O</i>-isopropylidene-L-<i>glycero</i>-2-tetrulose
  作者：Hajime Nagano、Mina Ohno、Yoko Miyamae、Yukie Kuno

  DOI：10.1246/bcsj.65.2814

  日期：1992.10

  Diastereoselectivity in the addition of Grignard reagents (RMgX) to 3,4-O-isopropylidene-1-O-triphenylmethyl-L-glycero-2-tetrulose (1) and 1-O-benzoyl-3,4-O-isopropylidene-L-glycero-2-tetrulose (2) depended remarkably on R, X, the solvent, and the reaction temperature. In the reaction of 1 in diethyl ether at 0 °C and 2 in tetrahydrofuran were obtained (2R,3S)-adducts with moderate to high diastereoselectivity

  将格氏试剂 (RMgX) 添加到 3,4-O-isopropylidene-1-O-triphenylmethyl-L-glycero-2-tetrulose (1) 和 1-O-benzoyl-3,4-O-isopropylidene- 时的非对映选择性L-glycero-2-tetrulose (2) 显着依赖于 R、X、溶剂和反应温度。在 0 °C 的乙醚中 1 和四氢呋喃中的 2 反应中获得了具有中到高非对映选择性的 (2R,3S)-加合物，而在 -78 °C 的乙醚中反应 2 (2S,3S) -加合物是主要产品。(2R)-2-羟甲基-2-壬基环氧乙烷和(2S)-2-羟甲基-2-十四烷基环氧乙烷被合成。
• Nagano, Hajime; Ohno, Mina; Miyame, Yoko, Chemistry Letters, 1990, # 3, p. 463 - 466
  作者：Nagano, Hajime、Ohno, Mina、Miyame, Yoko

  DOI：——

  日期：——
• Diastereoselectivity in Organometallic Additions to the Carbonyl Group of Protected Erythrulose Derivatives
  作者：J. Alberto Marco、Miguel Carda、Florenci González、Santiago Rodríguez、Encarna Castillo、Juan Murga

  DOI：10.1021/jo9716744

  日期：1998.2.1

  We have investigated a number of nucleophillic additions to L-erythrulose derivatives (4-12) bearing protective O-silyl, O-benzyl, and O-trityl groups in various relative positions. The results are discussed in the frame of chelated vs nonchelated transition states with additional support of previously published theoretical calculations. Sound evidence appears to exist for the formation of alpha-chelates as the key intermediates in nucleophillic additions to these alpha,beta-dioxygenated ketones. Since such evidence is still lacking in the case of beta-chelates, proposals of their intermediacy have been relegated in favor of the more solid Felkin-Anh model, which predicts the same stereochemical result. The behavior of these highly functionalized ketones does not always match that of structurally similar aldehydes.
• Stereoselective allylations of erythrulose derivatives under anhydrous conditions
  作者：Miguel Carda、Encarna Castillo、Santiago Rodrı́guez、Florenci González、J.Alberto Marco

  DOI：10.1016/s0957-4166(01)00262-2

  日期：2001.6

  We have investigated a number of nucleophilic additions or allylating reagents to several alpha,alpha ',beta -trioxygenated ketones (O-protected erythrulose derivatives), Reagents based on lithium. magnesium. copper and titanium stereoselectivities and did not display any recognizable trend in the sense of stereoselection. In contrast, reactions involving silicon and tin derivatives were highly stereoselective and gage rise to essentially a single diastereoisomer, the structure of which depended group. Thus, alpha,beta -di-O-benzylated derivatives experienced almost exclusive addition to the carbonyl Si on the type or protecting group side, whereas alpha,beta -O,O-alkylidene derivatives (dioxolane acetals) yielded the opposite diastereoisomers as a result of addition to the Re side. These results Suggest the intermediacy of a-chelates in the additions or silicon and tin reagents to the di-O-benzylated derivatives. In contrast, the opposite stereoisomers. formed in the reactions of dioxolanes. are believed to be formed through Felkin-Anh transition states, pointing to the reluctance of acetal ox gens to participate in chelated intermediates. (C) 2001 Published by Elsevier Science Ltd.