2,3,4-tri-O-acetyl-β-L-fucopyranosyl cyanide | 86651-65-2

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 2,3,4-tri-O-acetyl-β-L-fucopyranosyl cyanide
• 英文别名: [(2S,3R,4R,5R,6S)-4,5-diacetyloxy-6-cyano-2-methyloxan-3-yl] acetate
• CAS: 86651-65-2
• 化学式: C₁₃H₁₇NO₇
• 分子量: 299.28
• InChiKey: FZNCABDRPGXWPZ-HCTNGXQSSA-N

物化性质

• 沸点：
  388.4±42.0 °C(Predicted)
• 密度：
  1.26±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  21
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  112
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 4-二甲氨基吡啶 吡啶 、 甲醇 作用下， 反应 8.67h， 生成 2,3,4-tri-O-acetyl-β-L-fucopyranosyl cyanide
  参考文献：
  名称：

  Efficient Syntheses of β-Cyanosugars Using Glycosyl Iodides Derived from Per-O-silylated Mono- and Disaccharides

  摘要：

  [GRAPHICS]Reported herein is a general method for the efficient syntheses of a variety of beta -cyano glycosides through the activation of per-O-trimethylsllyl glycosides with TMSI to form alpha -glycosyl iodides, which undergo S(N)2-type displacement when treated with tetrabutylammonium cyanide. The cyanoglycosides were reduced under mild conditions using NaBH4 in the presence of catalytic CoCl2(H2O)(6) in THF/H2O to give the corresponding aminomethyl glycosides.

  DOI：

  10.1021/ol0160405

文献信息

• Synthesis and characterization of some anomeric pairs of per-O-acetylated aldohexopyranosyl cyanides (per-O-acetylated 2,6-anhydroheptononitriles). On the reaction of per-O-acetylaldohexopyranosyl bromides with mercuric cyanide in nitromethane
  作者：Robert Walter Myers、Yuan Chuan Lee

  DOI：10.1016/0008-6215(84)85065-x

  日期：1984.9

  per-O-acetylaldohexopyranosyl cyanides of D-galactose, L-fucose, D-glucose, and D-mannose, as well as of 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-beta-D-glucopyranosyl cyanide, are described. Cyanation of the readily available, per-O-acetylaldohexopyranosyl bromides with mercuric cyanide in nitromethane, and subsequent purification, gave the corresponding, crystalline glycosyl cyanides with a high degree of

  D-半乳糖，L-岩藻糖，D-葡萄糖和D-甘露糖以及3,4,6-三-O-乙酰-描述了2-脱氧-2-邻苯二甲酰亚胺基-β-D-吡喃葡萄糖基氰化物。在硝基甲烷中将氰化汞与现成的全-O-乙酰基醛基吡喃并吡喃糖基溴化物氰化，然后纯化，得到相应的结晶的糖基氰基氰化物，具有较高的1,2-反式立体选择性。因此，以20至79％的产率获得1,2-反式构型的全-O-乙酰化的醛-己二吡喃喃糖基氰化物，而以小于或等于8.4％的产率获得相应的1,2-顺式异构体。如此制备的1,2-反式：1,2-顺式端基异构体的比例大于或等于8.5：1。这些不可逆的氰化反应的主要副产物是全-O-乙酰化的1,2-O- [1-（异氰基和内氰基）亚乙基] aldohexopyranoses，得率高达40％。通过元素分析，化学转化，振动光谱以及13C和1H核磁共振光谱明确地确定了每个O-乙酰基乙二醛-吡喃并吡喃糖基氰化物的结构分配。描述了这些C
• Efficient synthesis of α-Aldopyranosyl cyanides via radical cyanation reactions
  作者：Jaime Martin、Luz Marina Jaramillo G、Peng George Wang

  DOI：10.1016/s0040-4039(98)01213-1

  日期：1998.8

  α-Aldopyranosylcyanides were efficiently prepared by a radical cyanation reaction between glycosyl bromides or glycosyl dithiocarbonates with tert-butylisocyanide, tris(trimethylsilyl)silane and 2,2′-azoisobutyronitriles.

  通过糖基溴化物或糖基二硫代碳酸酯与叔丁基异氰化物，三（三甲基甲硅烷基）硅烷和2,2'-偶氮异丁腈之间的自由基氰化反应，可以有效地制备α-醛基吡喃糖基氰化物。
• Efficient stereocontrolled synthesis of C-glycosides using glycosyl donors substituted by propane 1,3-diyl phosphate as the leaving group
  作者：Gurdial Singh、Hariprasad Vankayalapati

  DOI：10.1016/s0957-4166(01)00305-6

  日期：2001.7

  a- and beta -Glycosyl cyanides, per-O-acetyl-1,2-O-1-cyanoethylidenes and C-allyl glycopyranosides were efficiently prepared by treatment of 2,3,4-tri-O-acetyl-alpha,beta -L-rhamno-, L-fuco- and 2,3,4,6-tetra-O-acetyl-alpha,beta -D-galactopyranosyl propane-1,3-diyl phosphates with trimethylsilyl cyanide (TMSCN) and allyltrimethylsilane in the presence of trimethylsilyl triflate (TMSOTf). Similarly 2,3,4,6-tetra-O-benzyl-alpha,beta -D-manno- and D-glucopyranosyl propane-1,3-diyl phosphates were employed in the synthesis of C-glycosides. (C) 2001 Elsevier Science Ltd. All rights reserved.
• Palladium−Charcoal-Catalyzed Reduction of Tri-<i>O</i>-acetyl-β-<scp>l</scp>-Fucopyranosyl Cyanide:  A Route to Small Cluster Oligosaccharide Mimetics (SCOMs)
  作者：Pasit Phiasivongsa、Julie Gallagher、Chang-Nan Chen、Patrick R. Jones、Vyacheslav V. Samoshin、Paul H. Gross

  DOI：10.1021/ol020123j

  日期：2002.12.1

  Synthesis of glycosyl cyanides was optimized with a new catalyst system. Reduction of tri-O-acetyl-beta-L-fucopyranosyl cyanide with Pd-hydrogen, in the presence of Ac2O and Boc(2)O, gave N-protected-mono- and -di-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylmethyl)-amines, which allow for the syntheses of small cluster oligosaccharide mimetics of fucopyranosylomethyl-substituted ureas. From di-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylmethyl) amine was also prepared a carbamoyl chloride as a potentially useful synthon for preparation of more complex C-glycosidic conjugates.