6-O-tert-butyldiphenylsilyl-3-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose | 158226-41-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 6-O-tert-butyldiphenylsilyl-3-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose
• 英文别名: 3-deoxy-1,2-O-isopropylidene-6-O-tert-butyldiphenylsilyl-α-D-glucofuranose；(1R)-1-[(3aR,5S,6aR)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-2-[tert-butyl(diphenyl)silyl]oxyethanol
• CAS: 158226-41-6
• 化学式: C₂₅H₃₄O₅Si
• 分子量: 442.627
• InChiKey: SNCXVXCGNJRSED-KAOXLYBCSA-N

物化性质

• 沸点：
  498.8±45.0 °C(predicted)
• 密度：
  1.15±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.19
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 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：

  6-O-tert-butyldiphenylsilyl-3-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose 在 吡啶 、 间苯三酚 、 四丁基氟化铵 、 四丁基碘化铵 、 sodium hydride 、 sodium iodide 、 sodium nitrite 作用下， 以 四氢呋喃 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 129.0h， 生成 5-O-benzyl-3,6-dideoxy-1,2-O-isopropylidene-6-nitro-α-D-glucofuranose
  参考文献：
  名称：

  Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. Part 6: synthesis and incorporation into peptides of the first reported 2,3-dihydroxycyclopentanecarboxylic acid

  摘要：

  Herein we report the intramolecular alkylation of nitronates of methyl-5-O-benzy1-3,6-deoxy-6-nitro-alpha-D-glucofuranoside and methyl-5-O-benzyl-3,6-deoxy-6-nitro-alpha-D-glucofuranoside into the corresponding 2-oxabicyclo[2.2.1]heptane derivatives. Similarly, methyl-3-O-benzy1-5-deoxy-5-nitromethy1-13-beta-D-xylofuranoside and methyl-3-O-benzyl-5-deoxy-5-nitromethyl-alpha-D-xylofuranoside were cyclized to (1R,3R, 45,5R,7R)-7-benzyloxy-3-methoxy-5-nitro-2-oxabicyclo[2.2.1]heptane and (1R,3S,4S,5R,7R)-7-benzyloxy-3-methoxy-5-nitro-2-oxabicyclo[2.2.1]heptane, respectively. These 2-oxabicyclo[2.2.1]heptane derivatives were eventually transformed into enantiopure methyl (15,2S,3R,4S,5R)-2-amino-2,3-dihydroxycyclopentanecarboxylate and this novel beta-amino acid was incorporated into peptides. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2014.03.005
• 作为产物：
  描述：

  3-deoxy-1,2;5,6-di-O-isopropylidene-α-D-glucofuranoside 在 咪唑 、 水 、 溶剂黄146 作用下， 反应 9.0h， 生成 6-O-tert-butyldiphenylsilyl-3-deoxy-1,2-O-isopropylidene-α-D-ribo-hexofuranose
  参考文献：
  名称：

  C-Furanoside Synthesis via Intramolecular Cyclization

  摘要：

  具有正确绝对构型的多取代C-呋喃糖苷8，可通过二丙酮-d-葡萄糖方便地获得。这种经过脱保护的C-呋喃糖苷应是有机合成中的一种有用合成砌块，适用于天然产物合成。

  DOI：

  10.1055/s-1999-3157

文献信息

• Radical cyclization of highly functionalized precursors: stereocontrol of ring closure of acyclic 1-substituted-2,4-dihydroxylated hex-5-enyl radicals
  作者：Arlène Roland、Thierry Durand、David Egron、Jean-Pierre Vidal、Jean-Claude Rossi

  DOI：10.1039/a904206g

  日期：——

  Polysubstituted cyclopentane rings can be synthesized with good to high stereocontrol by radical cyclization using tributyltin hydride and a radical initiator, triethylborane–O2 in anhydrous xylene at room temperature. We have demonstrated that the nature (protected or unprotected) of the hydroxy functions in position 2 and 4 is responsible for the stereochemical cyclization outcome of acyclic 1-substituted-2

  可以通过自由基合成具有良好至高度立体控制的多取代环戊烷环 环化 使用 氢化三丁基锡 和自由基引发剂 三乙基硼烷室温下，-O 2在无水二甲苯中。我们已经证明，羟基在位置2和4上的官能团负责无环1取代的2,4-二羟基化的己5烯基化合物的立体化学环化结果。2,4-二醇的存在导致异前列腺素的全合成前体，而双保护基二醇得到非对映异构体的顺-反-syn前体。
• Synthesis of 3,5-dideoxy-5-iodo-1,2-O-isopropylidene-β-l-lyxo-hexofuranose derivatives
  作者：Benoît Rondot、Thierry Durand、Jean-Claude Rossi、Patrick Rollin

  DOI：10.1016/0008-6215(94)80013-8

  日期：1994.8
• C-Furanoside Synthesis via Intramolecular Cyclization
  作者：David Egron、Thierry Durand、Arlene Roland、Jean-Pierre Vidal、Jean-Claude Rossi

  DOI：10.1055/s-1999-3157

  日期：1999.4

  Polysubstituted C-furanoside 8, with the correct absolute configuration is readily available from diacetone-d-glucose. This C-furanoside after deprotection should be a useful synthon for natural product synthesis.

  具有正确绝对构型的多取代C-呋喃糖苷8，可通过二丙酮-d-葡萄糖方便地获得。这种经过脱保护的C-呋喃糖苷应是有机合成中的一种有用合成砌块，适用于天然产物合成。
• Stereocontrolled transformation of nitrohexofuranoses into cyclopentylamines via 2-oxabicyclo[2.2.1]heptanes. Part 6: synthesis and incorporation into peptides of the first reported 2,3-dihydroxycyclopentanecarboxylic acid
  作者：Amalia Estévez、Raquel G. Soengas、Pablo Thomas、Miguel Alegre、Rosalino Balo、Juan Carlos Estévez、Ramón J. Estévez

  DOI：10.1016/j.tetasy.2014.03.005

  日期：2014.4

  Herein we report the intramolecular alkylation of nitronates of methyl-5-O-benzy1-3,6-deoxy-6-nitro-alpha-D-glucofuranoside and methyl-5-O-benzyl-3,6-deoxy-6-nitro-alpha-D-glucofuranoside into the corresponding 2-oxabicyclo[2.2.1]heptane derivatives. Similarly, methyl-3-O-benzy1-5-deoxy-5-nitromethy1-13-beta-D-xylofuranoside and methyl-3-O-benzyl-5-deoxy-5-nitromethyl-alpha-D-xylofuranoside were cyclized to (1R,3R, 45,5R,7R)-7-benzyloxy-3-methoxy-5-nitro-2-oxabicyclo[2.2.1]heptane and (1R,3S,4S,5R,7R)-7-benzyloxy-3-methoxy-5-nitro-2-oxabicyclo[2.2.1]heptane, respectively. These 2-oxabicyclo[2.2.1]heptane derivatives were eventually transformed into enantiopure methyl (15,2S,3R,4S,5R)-2-amino-2,3-dihydroxycyclopentanecarboxylate and this novel beta-amino acid was incorporated into peptides. (c) 2014 Elsevier Ltd. All rights reserved.