benzyl 2,3-anhydro-α-L-ribopyranoside | 136984-98-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: benzyl 2,3-anhydro-α-L-ribopyranoside
• 英文别名: benzyl 2,3-anhydro-β-L-ribopyranoside；(1S,2R,5S,6S)-2-phenylmethoxy-3,7-dioxabicyclo[4.1.0]heptan-5-ol
• CAS: 136984-98-0
• 化学式: C₁₂H₁₄O₄
• 分子量: 222.241
• InChiKey: GOKFKMWTGYINLH-FIQHERPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.69
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  51.22
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  benzyl 2,3-anhydro-α-L-ribopyranoside 在 lithium bromide 作用下， 生成 (-)-(2S)-benzyloxy-2,5-dihydrofuran-4-carboxaldehyde
  参考文献：
  名称：

  Asymmetric diels-alder reaction between the chiral isoprene units 2-(r)-and (s)-benzyloxy-2,5-dihydro-4-furancarboxaldehyde and cyclopentadiene

  摘要：

  DOI：

  10.1016/s0040-4039(01)80899-6

文献信息

• Regioselective one pot approach to aminodeoxy sugars via aminosilanes
  作者：Abdul Malik、Najam-ul-Husain Kazmi、Abdul Qasim Khan、Zaheer Ahmad

  DOI：10.1039/c39870001073

  日期：——

  of regioisomerically pure aminodeoxy sugars (6)–(11) has been achieved by trans-diaxial cleavage of the oxirane ring in 2,3-anhydro sugars (1)–(5) with N,N-diethyltrimethylsilylamine or its N,N-dimethyl analogue, using AlCl3 as catalyst; the reagents work under mild conditions and avoid the difficulties which sometimes are encountered in ring-opening reactions of epoxy sugars.

  通过N，N-二乙基三甲基甲硅烷基胺在2,3-脱水糖（1）–（5）中环氧乙烷环的反式双轴裂解，已实现了一种区域异构纯氨基脱氧糖（6）–（11）的新型一步合成。或其Al，N-N-二甲基类似物，使用AlCl 3作为催化剂；该试剂在温和的条件下工作，避免了环氧糖开环反应中有时遇到的困难。
• Organoaluminium induced ring-opening of epoxypyranosides. V. Formal total synthesis of antimycin A3 and synthesis of (+)-blastmycinone.
  作者：Tord Inghardt、Torbjörn Frejd

  DOI：10.1016/s0040-4020(01)86575-3

  日期：1991.8

  Epoxide ring-opening of the benzyl 2,3-anhydro-alpha-L-ribopyranoside 6 with lithium butynyl(trimethyl)-aluminate followed by functional group interconventions gave the dihydroxy thioacetal 11, which was regio-selectively acylated with an L-threonine derivative. Acylation of the remaining hydroxyl group with isovaleryl chloride followed by thioacetal hydrolysis and oxidation of the liberated aldehyde gave 14, an intermediate in Kinoshita's antimycin A3 synthesis. The stereostructure of 11 was confirmed by converting it into (-)-blastmycino-lactol (18) which was acylated with isovaleryl chloride to give (+)-blastmycinone (19).
• INGHARDT, TORD;FREJD, TORBJORN, TETRAHEDRON, 47,(1991) N2, C. 6483-6492
  作者：INGHARDT, TORD、FREJD, TORBJORN

  DOI：——

  日期：——