1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol | 105938-02-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol
• 英文别名: (2R,3S,4R)-6-methyl-3,4-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-3,4-dihydro-2H-pyran
• CAS: 105938-02-1
• 化学式: C₂₈H₃₀O₄
• 分子量: 430.544
• InChiKey: BPRJSWGFGAQRNA-FCEKVYKBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  32
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  36.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol 在 sodium hydroxide 、 dimethyl sulfide borane 、 双氧水 作用下， 生成 (2S,3S,4R,5S,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-ol
  参考文献：
  名称：

  通过异头中心的极性反转形成C-糖苷

  摘要：

  经由相应的1-三丁基锡烷基衍生物获得的1-硫代三取代糖基的烷基化构成了新的进入C-糖苷的方法。

  DOI：

  10.1039/c39860000926
• 作为产物：
  描述：

  (3R,4R,5R)-5-hydroxy-3,4,6-tribenzyloxy-1-hexene 在 4-二甲氨基吡啶 、 四甲基乙二胺 、 Mo(CHCMe2Ph)2 、 四氯化钛 、 lead(II) chloride 、 锌 作用下， 以 甲苯 为溶剂， 反应 6.0h， 生成 1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1-C-methyl-D-arabino-hex-1-enitol
  参考文献：
  名称：

  通过烯烃复分解制备C-1缩醛。一种收敛灵活的C-糖苷合成方法（1）。

  摘要：

  DOI：

  10.1021/jo982331o

文献信息

• Synthesis of<i>C</i>-1 Alkyl and Aryl Glycals from Pyranosyl or Furanosyl Chlorides by Treatment with Organolithium Reagents
  作者：Ana M. Gómez、Ana Pedregosa、Marta Casillas、Clara Uriel、J. Cristóbal López

  DOI：10.1002/ejoc.200900417

  日期：2009.7

  Glycosyl chlorides, with ether or isopropylidene acetal protecting groups, readily available from furanoses or pyranoses, can be conveniently transformed into C-1 alkyl or aryl glycals by reaction with alkyl or aryl organolithium reagents.

  具有醚或亚异丙基缩醛保护基团的糖基氯可容易地从呋喃糖或吡喃糖中获得，可通过与烷基或芳基有机锂试剂反应方便地转化为 C-1 烷基或芳基糖醛。
• Glycosylidene Carbenes, Part 29 , Insertion into B−C and Al−C Bonds: Glycosylborinates, -boranes, and -alanes
  作者：Wolfgang Wenger、Andrea Vasella

  DOI：10.1002/1522-2675(20000705)83:7<1542::aid-hlca1542>3.0.co;2-f

  日期：2000.7.5

  Insertion of the glycosylidene carbenes derived from the diazirines 1, 14 and 15 into the B-alkyl bond of the B-alkyl-9-oxa-10-borabicyclo[3.3.2]decanes 5, 6, and 7 yielded the stable glycosylborinates 8/9 (55%, 55:45), 10/11 (31%, 65:35), 12/13 (47%, 60:40), 16/17 (55%, 55:45), 18/19 (47%, 45:55), and 20/21 (31%, 30:70). Crystal-structure analysis of 17 and NOEs of 9 and 19 show that 17 9, and 19 adopt similar conformations. The glycosylborinates are stable under acidic, basic and thermal conditions. The unprotected glycosylborinate 25 was obtained in 80% by hydrogenolysis of 12. Insertion of the glycosylidene carbene derived from the diazirine 1 into a B-C bond of BEt3, BBu3, and BPh3 led to unstable glycosylboranes that were oxidised to yield the hemiacetals 29 (55%), 31 (45%), and 33 (48%), respectively, besides the glucals 30 (13%), 32 (20%), and 34 (20%), respectively. Insertion of the glycosylidene carbenes derived from 14 and 15 into a B - C bond of BEt3 led exclusively to hemiacetals; only 15 yielding traces of the glucal 40 besides the hemiacetal 39. The glycosylidene carbene derived from 1 reacted with AL(Bu-1), and AlMe3 to generate reactive glycosylalanes that were hydrolysed, yielding the C-glycosides 46 (21%) and 49 (30%), respectively besides the glucals 48 (26%) and 51 (30%); deuteriolysis instead of protonolysis led to the monodeuterio analogues of 46 and 49, respectively, which possess an equatorial H-2-atom at the anomeric center.
• Preparation and use of lithiated glycals: vinylic deprotonation versus tin-lithium exchange from 1-tributylstannyl glycals1
  作者：Patrick Lesimple、Jean-Marie Beau、Guy Jaurand、Pierre Sinaÿ

  DOI：10.1016/s0040-4039(00)85432-5

  日期：1986.1
• Expeditious entry to C-alkyl and C-aryl pyranoid glycals: reaction of anomeric glycosyl chlorides with organolithiums
  作者：Ana M. Gómez、Marta Casillas、Serafín Valverde、J. Cristóbal López

  DOI：10.1039/cc9960002357

  日期：——

  Treatment of ether-substituted glycopyranosyl chlorides with organolithium reagents gives the corresponding C-glycals in acceptable to good yields.
• Preparation of <i>C</i>-1 Glycals via Olefin Metathesis. A Convergent and Flexible Approach to <i>C</i>-Glycoside Synthesis¹
  作者：Daniel Calimente、Maarten H. D. Postema

  DOI：10.1021/jo982331o

  日期：1999.3.1