(E)-6,7-didehydro-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octodialo-1,5-pyranose | 100759-67-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: (E)-6,7-didehydro-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octodialo-1,5-pyranose
• 英文别名: (6E)-6,7-Didesoxy-1,2:3,4-di-O-isopropyliden-α-D-galacto-oct-6-enodialdopyranose-(1,5)；trans-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-oct-6-enodialdo-1,5-pyranose；(E)-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-oct-6-enodialdo-1,5-pyranose；(E)-3-[(1S,2R,6R,8R,9S)-4,4,11,11-tetramethyl-3,5,7,10,12-pentaoxatricyclo[7.3.0.02,6]dodecan-8-yl]prop-2-enal
• CAS: 100759-67-9；50256-79-6
• 化学式: C₁₄H₂₀O₆
• 分子量: 284.309
• InChiKey: RLJNJVHALUZOAM-SDCVYYIZSA-N

物化性质

• 沸点：
  395.2±42.0 °C(Predicted)
• 密度：
  1.183±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (E)-6,7-didehydro-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octodialo-1,5-pyranose 在 palladium on activated charcoal 氢气 、 溶剂黄146 作用下， 以 水 为溶剂， 反应 0.17h， 生成 6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octodialdo-1,5-pyranose
  参考文献：
  名称：

  Lehmann, Jochen; Scheuring, Markus, Liebigs Annalen der Chemie, 1990, p. 271 - 275

  摘要：

  DOI：
• 作为产物：
  描述：

  (Z)-N-benzyl-(1,2:3,4-di-O-isopropylidene-α-D-galactopyranos-6-ylidene)amine N-oxide 在 碳酸氢钠 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 24.75h， 生成 (E)-6,7-didehydro-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-octodialo-1,5-pyranose
  参考文献：
  名称：

  Higher glycosamino acid precursors: C7 and C8 aminodialdoses via regio- and stereoselective [3+2] cycloaddition of vinyl trimethylsilane to C-glycosyl nitrones

  摘要：

  Protected C-7 and C-8 aminodialdoses were prepared stereoselectively from readily available C-5 and C-6 monosaccharide N-benzyl nitrones, by regio- and diastereoselective 1,3-dipolar cycloaddition reactions with vinyl trimethylsilane, followed by acetyl chloride-mediated cleavage of the 5-(trimethylsilyl)isoxazolidine formed. The cycloaddition reaction took place in moderate to good global yields (67-74%); estimation of diastereoselectivities from isolated yields showed total endo preference for the reaction of the D-galacto configured nitrone and high endo preference for the D-ribo analogue, but exo preference for the D-Xylo configured substrate. Attack on the re face of the nitrone was predominant in all cases. The absolute configuration of one of the protected 3-(alpha-D-galacto-pentopyranos-5-yl)isoxazolidine products was assigned by X-ray crystallographic analysis, allowing correlation of the configuration at the new stereogenic centre in the corresponding aminodialdose. For non-crystalline isoxazolidines, configurations were assigned on the basis of NOESY experiments and/or chemical correlation. Combined yields of aminodialdoses coming from isoxazolidines having identical configuration at C(3) sometimes reached high values (up to 90%). These compounds are precursors of higher-chain glycosamino acids. (C) 2002 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(02)00543-8

文献信息

• The Synthesis of Some Octenoses as Potential Precursors to Lincosamine, a Derived Portion of the Antibiotic Lincomycin
  作者：RV Stick、DMG Tilbrook

  DOI：10.1071/ch9901643

  日期：——

  Methyl (E)-2,3-di-O-benzyl-6,7,8-trideoxy-α-D-galacto-oct-6-enopyranoside, a potential precursor to lincosamine, has been prepared from both methyl α-D-galactopyranoside and methyl α-D-glucopyranoside, with the required inversion at C4 in the latter sequence being effected by a conventional oxidation-reduction. As well, (E)-6,7-dideoxy-1,2: 3,4-di-O-isopropylidene-α-D-galacto-oct-6-enose and (E)- and (Z)-6,7,8- trideoxy-1,2:3,4-di-O-isopropylidene-α-D-galacto-oct-6-enose have been prepared from 1,2: 3,4-di-O-isopropylidene-α-D-galactose.

  甲基(E)-2,3-二-O-苄基-6,7,8-三脱氧-α-D-半乳糖-辛-6-烯吡喃糖苷是一种潜在的林可胺前体，已从甲基α-D-吡喃半乳糖苷和甲基α-D-吡喃葡萄糖苷中制备出来，后者序列中 C4 所需的反转是通过传统的氧化还原法实现的。此外，(E)-6,7-二脱氧-1,2:3,4-二-O-异亚丙基-α-D-半乳糖-辛-6-烯糖和(E)-和(Z)-6,7,8-三脱氧-1,2:3,4-二-O-异亚丙基-α-D-半乳糖-辛-6-烯糖也是由 1,2:3,4-二-O-异亚丙基-α-D-半乳糖制备的。
• First general methods toward aldehyde enolphosphates
  作者：Nicolas Barthes、Claude Grison

  DOI：10.1016/j.bioorg.2011.11.006

  日期：2012.2

  We herein report two innovative methods toward aldehyde enolphosphates and the first saccharidic aldehyde enolphosphates. Aldehyde enolphosphate function is worthwhile to be considered as a good phosphoenolpyruvate analogue.

  我们在此报告了针对醛烯醇磷酸酯和第一种糖醛醛烯醇磷酸酯的两种创新方法。醛烯醇磷酸酯的功能值得认为是良好的磷酸烯醇丙酮酸类似物。
• A synthetic approach to olguine: A model study
  作者：Rosa Ma. Rabanal、Javier Escudero、Manuel Martin-Lomas、Serafin Valverde、Aurea Perales、Jose Fayos

  DOI：10.1016/s0008-6215(00)90754-7

  日期：1985.8
• Brimacombe, John S.; Hanna, Roderick; Kabir, Abul K. M. S., Journal of the Chemical Society. Perkin transactions I, 1986, p. 815 - 822
  作者：Brimacombe, John S.、Hanna, Roderick、Kabir, Abul K. M. S.、Bennett, Frank、Taylor, Ian D.

  DOI：——

  日期：——
• Higher-carbon sugars: on the stereochemistry of the oxidation of some unsaturated carbohydrate derivatives with osmium tetraoxide
  作者：John S. Brimacombe、Roderick Hanna、Frank Bennett

  DOI：10.1016/s0008-6215(00)90791-2

  日期：1985.1