α-L-boivinose | 2053-00-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: α-L-boivinose
• 英文别名: L-boivinose；L-lyxo-2,6-dideoxy-hexose；α-L-lyxo-2,6-dideoxy-hexopyranose；2,6-Dideoxy-α-lyxo-hexopyranose；α-L-oliopyranose；(2R,4R,5S,6S)-6-methyloxane-2,4,5-triol
• CAS: 2053-00-1；17050-70-3；22899-74-7；25029-50-9；45742-39-0；45742-40-3；49871-87-6；51020-42-9；62413-93-8；71328-50-2；74112-04-2；74112-05-3；74112-09-7；74112-10-0；74112-11-1；74112-14-4；78185-01-0；78185-02-1；89253-95-2；89253-96-3；89253-97-4；97276-35-2；102850-49-7；102850-50-0；110043-58-8；138458-66-9；138458-67-0；139630-51-6；139683-22-0
• 化学式: C₆H₁₂O₄
• 分子量: 148.159
• InChiKey: FDWRIIDFYSUTDP-SLPGGIOYSA-N

物化性质

• 沸点：
  320.1±42.0 °C(Predicted)
• 密度：
  1.366±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  10
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  69.9
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  rel-(5R,6S)-5,6-Dihydro-5-hydroxy-6-methyl-2H-pyran-2-one 在 sodium tetrahydroborate 、 过氧化氢苯甲酰 、 二苯基二硒醚 、 sodium acetate 、 sodium cyanoborohydride 、 potassium carbonate 、 溶剂黄146 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 异丙醇 、 苯 为溶剂， 反应 46.0h， 生成 α-L-boivinose
  参考文献：
  名称：

  A divergent strategy for constructing a sugar library containing 2,6-dideoxy sugars and uncommon sugars with 4-substitution

  摘要：

  A practical strategy has been developed for delivering 2,6-dideoxy sugars and uncommon sugars with 4-substitution. This strategy employed Ferrier rearrangement reaction and BF3 center dot OEt2-induced peroxidation to construct key intermediates 2,3-unsaturated glycosides and alpha,beta-unsaturated lactones from peracetyl rhamnal. After further derivatization, four uncommon sugars with 4-substitution and eight uncommon sugar units with 3,4-disubstitution were successfully synthesized. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.07.019

文献信息

• On the steric course of the addition of diallylzinc onto α,β-dialkoxy chiral carbonyl compounds: stereospecific synthesis of 2,6-dideoxysugars of the -series
  作者：Giovanni Fronza、Claudio Fuganti、Piero Grasselli、Giuseppe Pedrocchi-Fantoni、Carlo Zirotti

  DOI：10.1016/s0040-4039(00)88370-7

  日期：1982.1

  6-dideoxy sugars -digitoxose (14), 2-deoxy--fucose (15) and -mycarose (16) from the C4 and C5 chiral synthons (1), (2) and (3), through the intermediacy of the C7 adducts (4), (8) and (12), obtained by addition of diallylzinc onto (1), (2) and (3), is reported.

  由C 4和C 5手性合成子（1），（2）和（3）合成2,6-二脱氧糖-洋地黄糖（14），2-脱氧--岩藻糖（15）和-mycarose（16）。），报道了通过在（1），（2）和（3）上添加二烯丙基锌而获得的C 7加合物（4），（8）和（12）的中间体。
• A divergent strategy for constructing a sugar library containing 2,6-dideoxy sugars and uncommon sugars with 4-substitution
  作者：Guisheng Zhang、Lei Shi、Qingfeng Liu、Jingmei Wang、Lu Li、Xiaobing Liu

  DOI：10.1016/j.tet.2007.07.019

  日期：2007.9

  A practical strategy has been developed for delivering 2,6-dideoxy sugars and uncommon sugars with 4-substitution. This strategy employed Ferrier rearrangement reaction and BF3 center dot OEt2-induced peroxidation to construct key intermediates 2,3-unsaturated glycosides and alpha,beta-unsaturated lactones from peracetyl rhamnal. After further derivatization, four uncommon sugars with 4-substitution and eight uncommon sugar units with 3,4-disubstitution were successfully synthesized. (c) 2007 Elsevier Ltd. All rights reserved.