Benzyl 2,6-Dideoxy-β-D-arabino-hexopyranoside | 90762-85-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Benzyl 2,6-Dideoxy-β-D-arabino-hexopyranoside
• 英文别名: phenylmethyl β-D-olivopyranoside；(2R,3S,4R,6R)-2-methyl-6-phenylmethoxyoxane-3,4-diol
• CAS: 90762-85-9
• 化学式: C₁₃H₁₈O₄
• 分子量: 238.284
• InChiKey: HKVKPOJNFRNEJA-OJAKKHQRSA-N

物化性质

• 沸点：
  387.8±42.0 °C(predicted)
• 密度：
  1.21±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  58.9
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  phenylmethyl 3-O-(p-nitrobenzoyl)-β-D-olivopyranoside 在 甲醇 、 potassium carbonate 作用下， 反应 2.0h， 以98%的产率得到Benzyl 2,6-Dideoxy-β-D-arabino-hexopyranoside
  参考文献：
  名称：

  De Novo Synthesis of the Trisaccharide Subunit of Landomycins A and E

  摘要：

  A highly enantio- and diastereoselective synthesis of alpha-L-rhodinose, beta-D-olivose as well as the trisaccharide portion of landomycin A from achiral acetyl furan has been developed. The key transformations include the palladium-catalyzed glycosylation, Myers' reductive rearrangement, diastereoselective dihydroxylation, and regioselective Mitsunobu inversion. A Mitsunobu reaction on a six member ring cis-1,2-diol was found to chemoselectively discriminate between equatorial and axial alcohols and to stereoselectively convert cis-1,2-diol into ant 1,2-diol.

  DOI：

  10.1021/ol800697k

文献信息

• Preparation of .alpha.- and .beta.-linked disaccharides of 2,6-dideoxy-D-arabino-hexose. Synthesis of bamflalactone
  作者：Inge Lundt、Joachim Thiem、Archibald Prahst

  DOI：10.1021/jo00191a006

  日期：1984.8
• US6353095B1
  申请人：——

  公开号：US6353095B1

  公开（公告）日：2002-03-05
• [EN] KETOALDONIC ACIDS HAVING FORMED STEREOGENIC CENTERS OF R CONFIGURATION: METHODS AND COMPOSITIONS
  申请人：THE SCRIPPS RESEARCH INSTITUTE

  公开号：WO1993006227A1

  公开（公告）日：1993-04-01

  (EN) The present invention provides a ketoaldonic acid such as an octulosonic or nonulosonic acid having formed stereogenic center of R configuration, as well as methods of synthesizing the same.(FR) L'invention se rapporte à un acide cétoaldonique tel qu'un acide octulosonique ou nonulosonique ayant un centre stéréogénique formé présentant une configuration en R, ainsi qu'à des procédés de synthèse d'un tel acide.
• De Novo Synthesis of the Trisaccharide Subunit of Landomycins A and E
  作者：Maoquan Zhou、George A. O’Doherty

  DOI：10.1021/ol800697k

  日期：2008.6.5

  A highly enantio- and diastereoselective synthesis of alpha-L-rhodinose, beta-D-olivose as well as the trisaccharide portion of landomycin A from achiral acetyl furan has been developed. The key transformations include the palladium-catalyzed glycosylation, Myers' reductive rearrangement, diastereoselective dihydroxylation, and regioselective Mitsunobu inversion. A Mitsunobu reaction on a six member ring cis-1,2-diol was found to chemoselectively discriminate between equatorial and axial alcohols and to stereoselectively convert cis-1,2-diol into ant 1,2-diol.