1,2-O-isopropylidene-3,5-di-O-methanesulfonyl-α-D-xylofuranose | 75252-13-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-isopropylidene-3,5-di-O-methanesulfonyl-α-D-xylofuranose
• 英文别名: 1,2-O-isopropylidene-3,5-di-O-methylsulfonyl-α-D-xylofuranose；1,2-O-isopropylidene-3,5-di-methylsulfonyl-α-D-xylofuranose；O¹,O²-isopropylidene-O³,O⁵-bis-methanesulfonyl-α-D-xylofuranose；O¹,O²-Isopropyliden-O³,O⁵-bis-methansulfonyl-α-D-xylofuranose；[(3aR,5R,6S,6aR)-2,2-dimethyl-6-methylsulfonyloxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl methanesulfonate
• CAS: 75252-13-0
• 化学式: C₁₀H₁₈O₉S₂
• 分子量: 346.38
• InChiKey: XOTMTXXKAZRBNU-BZNPZCIMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  131
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  1,2-O-isopropylidene-3,5-di-O-methanesulfonyl-α-D-xylofuranose 在 吡啶 、 三甲基氯硅烷 、 甲酸 、 叠氮化锂 、 三氟甲磺酸三甲基硅酯 、 六甲基二硅氮烷 作用下， 以 六甲基磷酰三胺 为溶剂， 反应 4.5h， 生成 1-((2R,3R,4S,5R)-4-Azido-5-azidomethyl-3-hydroxy-tetrahydro-furan-2-yl)-1H-pyrimidine-2,4-dione
  参考文献：
  名称：

  Aminonucleosides and their Derivatives; VII¹. Synthesis of the 3′,5′-Dideoxy-3′,5′-diaminonucleosides

  摘要：

  DOI：

  10.1055/s-1980-29121
• 作为产物：
  描述：

  1,2:3,5-双-O-异亚丙基-alpha-D-呋喃木糖 在 吡啶 、 盐酸 作用下， 反应 0.5h， 生成 1,2-O-isopropylidene-3,5-di-O-methanesulfonyl-α-D-xylofuranose
  参考文献：
  名称：

  Synthesis of Different 3,5‐Diazidofuranoses: A New and General Synthesis Pathway

  摘要：

  Diamino- and diazidofuranoses represent useful precursors, for example, for the synthesis of substituted nucleosides and metal complexes, respectively. Known procedures for their synthesis lack the availability of cheap starting materials, adequate yields, and the access to all possible diastereomeres. Therefore, 3,5-diazido-3,5-dideoxy- and - 2,3,5- trideoxyfuranoses both with ribo- and xylo- configuration were prepared using different approaches.

  DOI：

  10.1080/07328300701540175

文献信息

• Synthesis of Cyclic γ-Amino Acids for Foldamers and Peptide Nanotubes
  作者：Nuria Rodríguez-Vázquez、Stephan Salzinger、Luis F. Silva、Manuel Amorín、Juan R. Granja

  DOI：10.1002/ejoc.201201565

  日期：2013.6

  Cyclic γ-amino acids are molecular building blocks of great interest in peptide and foldamer chemistry, as they allow the preparation of new structures that are not found in Nature. In this paper, we describe the synthesis of cyclic γ-amino acids that have a cis relationship between the amino and the carboxylic acid groups. This arrangement, in most cases, induces the resulting peptides to adopt a

  环状γ-氨基酸是肽和折叠体化学中非常受关注的分子构建块，因为它们允许制备自然界中未发现的新结构。在本文中，我们描述了在氨基和羧酸基团之间具有顺式关系的环状 γ-氨基酸的合成。在大多数情况下，这种排列会导致生成的肽采用扁平构象，这使得它们适用于采用 β-折叠型结构的折叠体的设计。
• Hydroxy group interactions in stannylated carbohydrates. Structures and thermal stabilities of 5-deoxy-5-C-(Ph₃Sn)-1,2-O-isopropylidene-α-<scp>D</scp>-xylofuranose, 5-deoxy-5-C-(IPh₂Sn)-1,2-O-isopropylidene-α-<scp>D</scp>- and -<scp>L</scp>-xylofuranose, and 5-deoxy-5-C-(I₂PhSn)-1,2-O-isopropylidene-α-<scp>D</scp>- and -<scp>L</scp>-xylofuranose
  作者：Lynne A. Burnett、Vitor F. Ferreira、R. Alan Howie、Helena Rufino、Janet M. S. Skakle、James L. Wardell、Solange M. S. V. Wardell

  DOI：10.1039/b204675j

  日期：——

  Structures and thermal stabilities of 5-deoxy-5-C-(Ph3Sn)-1,2-O-isopropylidene-α-D-xylofuranose, [(D)-3], 5-deoxy-5-C-(IPh2Sn)-1,2-O-isopropylidene-α-D- and -L-xylofuranose, [(D)-4 and (L)-4], and 5-deoxy-5-C-(I2PhSn)-1,2-O-isopropylidene-α-D- and -L-xylofuranose, [(D)-5 and (L)-5], are reported. The hydroxy groups in the stannylated xylofuranose derivatives, 3–5, exhibit roles as Lewis bases, Brønsted acids and hydrogen bonding centres. The 5-deoxy-1,2-O-isopropylidene-α-D- and –L-xylofuran-5-yl ligands operate as C5,O4 chelating ligands (4-membered chelate rings) in 3, C5,O3 chelating ligands in 4 (molecule 2) and 5 (5-membered chelate rings), and a C5,O4,O3 tridentate ligand in 4 (molecule 1) [both 4- and 5-membered chelate rings]. Compounds 4, in contrast to 3 and 5, undergo slow proton-dephenylation reactions in chloroform solutions at ambient temperature. All decompose on heating at 145–155 °C with evolution of PhH, Me2CO and H2O. The trigonal bipyramidal tin centres in (D)-5 and (L)-5 are chiral, at least in the solid state. Different modes of O–H–O bonding are found in 3, 4 (molecule 2) and 5 compared to that in 4 (molecule 1).

  5-deoxy-5-C-(Ph3Sn)-1,2-O-isopropidylene-α-D-xylofuranose, [(D)-3], 5-deoxy-5-C-(IPh2Sn)-1、报告了 5-脱氧-5-C-(I2PhSn)-1,2-O-异亚丙基δ-±-D-和-L-氧基呋喃糖[(D)-4 和 (L)-4]，以及 5-脱氧-5-C-(I2PhSn)-1,2-O-异亚丙基δ-D-和-L-氧基呋喃糖[(D)-5 和 (L)-5]。链烷酰化的呋喃木糖衍生物 3â5 中的羟基具有路易斯碱、布氏酸和氢键中心的作用。5-脱氧-1,2-O-异亚丙基δ-D-和α-L-氧杂呋喃-5-基配体在 3 中作为 C5,O4 螯合配体（4 元螯合环）起作用，在 4（分子 2）和 5（5 元螯合环）中作为 C5,O3 螯合配体起作用，在 4（分子 1）中作为 C5,O4,O3 三叉配体起作用[同时具有 4 元和 5 元螯合环]。与 3 和 5 相反，化合物 4 在常温下的氯仿溶液中会发生缓慢的质子-二苯甲基化反应。在 145-155°C 的温度下加热时，所有化合物都会分解，生成 PhH、Me2CO 和 H2O。至少在固态下，(D)-5 和 (L)-5 中的三叉双锥锡中心是手性的。与 4（分子 1）相比，在 3、4（分子 2）和 5 中发现了不同的 OâHâO 成键模式。
• Synthesis of some pyrrolo[2,3-d]pyrimidine and 1,2,3-triazole isonucleosides
  作者：Ratnakar R. Talekar、Richard H. Wightman

  DOI：10.1016/s0040-4020(97)00102-6

  日期：1997.3

  Nucleoside analogues 8, 9, 10 and 11, in which a pyrrolo[23-d]pyrimidine ring is linked to a 2-hydroxymethyl-3-hydroxytetrahydrofuran, have been prepared. The azide 16 used as an intermediate in the routes to these compounds also gave access to the 1, 2, 3-triazole isonucleosides 12 and 13. (C) 1997 Elsevier Science Ltd.
• Ueber derivate der d-xylose
  作者：Burckhardt Helferich、Martin Burgdorf

  DOI：10.1016/0040-4020(58)80023-x

  日期：1958.1
• Hughes, Neil A.; Wood, Christopher J., Journal of the Chemical Society. Perkin transactions I, 1986, p. 695 - 700
  作者：Hughes, Neil A.、Wood, Christopher J.

  DOI：——

  日期：——