C-(tert-butyldimethylsilyloxy)-2,3-O-isopropylidene-L-erythrofuranose | 1025063-30-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: C-(tert-butyldimethylsilyloxy)-2,3-O-isopropylidene-L-erythrofuranose
• 英文别名: (2S,3S)-2-((tert-butyldimethylsilyl)oxy)methyl-2,3-O-isopropylidene-L-erythrofuranose；(3aS,6aS)-3a-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-6,6a-dihydro-4H-furo[3,4-d][1,3]dioxol-4-ol
• CAS: 1025063-30-2
• 化学式: C₁₄H₂₈O₅Si
• 分子量: 304.459
• InChiKey: DZNCUKLBKWWMBY-PEMBBPQUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.25
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  C-(tert-butyldimethylsilyloxy)-2,3-O-isopropylidene-L-erythrofuranose 在 咪唑 、 四氧化锇 、 重铬酸吡啶 、 正丁基锂 、 硫酸 、 四丁基氟化铵 、 乙酸酐 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 叔丁醇 为溶剂， 反应 60.83h， 生成
  参考文献：
  名称：

  Synthesis of Carbohydrates in Mineral-Guided Prebiotic Cycles

  摘要：

  One present obstacle to the "RNA-first" model for the origin of life is an inability to generate reasonable "hands off" scenarios for the formation of carbohydrates under conditions where they might have survived for reasonable times once formed. Such scenarios would be especially compelling if they deliver pent(ul)oses, five-carbon sugars found in terran genetics, and exclude other carbohydrates (e.g., aldotetroses) that may also be able to function in genetic systems. Here, we provide detailed chemical analyses of carbohydrate premetabolisin, showing how borate, molybdate, and calcium minerals guide the formation of tetroses (C(4)H(8)O(4)), heptoses (C(7)H(14),O(7)), and pentoses (C(5)H(10)O(5)), including the ribose found in RNA, in "hands off" experiments, starting with formaldehyde and glycoaldehyde. These results show that pent(ul)oses would almost certainly have formed as stable borate complexes on the surface of an early Earth beneath a humid CO(2) atmosphere suffering electrical discharge. While aldotetroses form extremely stable complexes with borate, they are not accessible by pathways plausible under the most likely early Earth scenarios. The stabilization by borate is not, however, absolute. Over longer times, material is expected to have passed from borate-bound pent(ul)oses to a branched heptulose, which is susceptible to Cannizzaro reduction to give dead end products. We show how this fate might be avoided using molybdate-catalyzed rearrangement of a branched pentose that is central to borate-moderated cycles that fix carbon from formaldehyde. Our emerging understanding of the nature of the early Earth, including the presence of hydrated rocks undergoing subduction to form felsic magmas in the early Hadean eon, may have made borate and molydate species available to prebiotic chemistry, despite the overall "reduced" state of the planet.

  DOI：

  10.1021/ja201769f
• 作为产物：
  描述：

  2,3-O-isopropylidene-L-erythrofuranose 在 咪唑 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 10.0h， 生成 C-(tert-butyldimethylsilyloxy)-2,3-O-isopropylidene-L-erythrofuranose
  参考文献：
  名称：

  新型C支化多羟基化环硝酮的合成

  摘要：

  摘要以市售的1-阿拉伯糖为原料，合成了新型的C-支化多羟基化环硝酮25，该化合物可作为合成C-支化的吡咯烷亚氨基糖的有价值的中间体。

  DOI：

  10.1016/j.cclet.2016.12.033

文献信息

• Facile synthesis of 6a-carba-β-d-fructopyranose through an RCM approach
  作者：Sotirios M. Totokotsopoulos、Alexandros E. Koumbis、John K. Gallos

  DOI：10.1016/j.tet.2008.02.046

  日期：2008.4

  A new synthetic approach toward 6a-carba-beta-D-fructopyranose, a non-nutritive sweetener related to topiramate, is described. This scheme uses 2-C-hydroxymethyl-L-erythrose acetonide as starting material and efficiently delivers the target compound applying an RCM protocol for the construction of the carbocycle ring. (c) 2008 Elsevier Ltd. All rights reserved.
• Synthesis of Carbohydrates in Mineral-Guided Prebiotic Cycles
  作者：Hyo-Joong Kim、Alonso Ricardo、Heshan I. Illangkoon、Myong Jung Kim、Matthew A. Carrigan、Fabianne Frye、Steven A. Benner

  DOI：10.1021/ja201769f

  日期：2011.6.22

  One present obstacle to the "RNA-first" model for the origin of life is an inability to generate reasonable "hands off" scenarios for the formation of carbohydrates under conditions where they might have survived for reasonable times once formed. Such scenarios would be especially compelling if they deliver pent(ul)oses, five-carbon sugars found in terran genetics, and exclude other carbohydrates (e.g., aldotetroses) that may also be able to function in genetic systems. Here, we provide detailed chemical analyses of carbohydrate premetabolisin, showing how borate, molybdate, and calcium minerals guide the formation of tetroses (C(4)H(8)O(4)), heptoses (C(7)H(14),O(7)), and pentoses (C(5)H(10)O(5)), including the ribose found in RNA, in "hands off" experiments, starting with formaldehyde and glycoaldehyde. These results show that pent(ul)oses would almost certainly have formed as stable borate complexes on the surface of an early Earth beneath a humid CO(2) atmosphere suffering electrical discharge. While aldotetroses form extremely stable complexes with borate, they are not accessible by pathways plausible under the most likely early Earth scenarios. The stabilization by borate is not, however, absolute. Over longer times, material is expected to have passed from borate-bound pent(ul)oses to a branched heptulose, which is susceptible to Cannizzaro reduction to give dead end products. We show how this fate might be avoided using molybdate-catalyzed rearrangement of a branched pentose that is central to borate-moderated cycles that fix carbon from formaldehyde. Our emerging understanding of the nature of the early Earth, including the presence of hydrated rocks undergoing subduction to form felsic magmas in the early Hadean eon, may have made borate and molydate species available to prebiotic chemistry, despite the overall "reduced" state of the planet.
• Synthesis of a novel C-branched polyhydroxylated cyclic nitrone
  作者：Qing-Kun Wu、Yi-Xian Li、Yue-Mei Jia、Chu-Yi Yu

  DOI：10.1016/j.cclet.2016.12.033

  日期：2017.4

  Abstract A novel C-branched polyhydroxylated cyclic nitrone 25, which could be a valuable intermediate for the synthesis of C-branched pyrrolidine iminosugars, was synthesized starting from the commercially available l -arabinose in 29.0% total yield.

  摘要以市售的1-阿拉伯糖为原料，合成了新型的C-支化多羟基化环硝酮25，该化合物可作为合成C-支化的吡咯烷亚氨基糖的有价值的中间体。