methyl 6-O-benzoyl-2,3-O-isopropylidene-4-deoxy-α-D-lyxo-hexopyranoside | 73635-98-0

• 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: methyl 6-O-benzoyl-2,3-O-isopropylidene-4-deoxy-α-D-lyxo-hexopyranoside
• 英文别名: methyl 6-O-benzoyl-4-deoxy-2,3-O-isopropylidene-α-D-lyxo-hexopyranoside
• CAS: 73635-98-0
• 化学式: C₁₇H₂₂O₆
• 分子量: 322.358
• InChiKey: NADIWGLNKJLHSO-YXWQFLTLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.12
• 重原子数：
  23.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  63.22
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  methyl 6-O-benzoyl-2,3-O-isopropylidene-4-deoxy-α-D-lyxo-hexopyranoside 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 20.0h， 以83%的产率得到methyl 2,3-O-isopropylidene-4-deoxy-α-D-lyxo-hexopyranoside
  参考文献：
  名称：

  Synthesis of 4-deoxy-D-lyxo-hexose

  摘要：

  DOI：

  10.1021/jo01301a041
• 作为产物：
  描述：

  methyl 2,3-O-isopropylidene-4-deoxy-α-D-lyxo-hexopyranoside 以80%的产率得到methyl 6-O-benzoyl-2,3-O-isopropylidene-4-deoxy-α-D-lyxo-hexopyranoside
  参考文献：
  名称：

  从 D-甘露糖中制备光活性中间体的美登醇类化合物的合成研究

  摘要：

  美登素的光学活性中间体（15 和 23）是由 D-甘露糖通过甲基锂的杂共轭加成作为关键步骤合成的。

  DOI：

  10.1246/cl.1981.457

文献信息

• Buchanan, J. Grant; Stoddart, Jane; Wightman, Richard H., Journal of the Chemical Society. Perkin transactions I, 1994, # 11, p. 1417 - 1426
  作者：Buchanan, J. Grant、Stoddart, Jane、Wightman, Richard H.

  DOI：——

  日期：——
• Synthesis of deoxy sugars. Deoxygenation by treatment with N,N'-thiocarbonyldiimidazole/tri-n-butylstannane
  作者：James R. Rasmussen、Cheryl J. Slinger、Rebecca J. Kordish、Dana D. Newman-Evans

  DOI：10.1021/jo00337a004

  日期：1981.11
• Synthesis of monodeoxy analogues of the trisaccharide α-d-Glcp-(1→3)-α-d-Manp-(1→2)-α-d-ManpOMe recognised by Calreticulin/Calnexin
  作者：Emiliano Gemma、Martina Lahmann、Stefan Oscarson

  DOI：10.1016/j.carres.2006.03.015

  日期：2006.7

  Six (3,4,4',6',3" or 6")-monodeoxy analogues of the title trisaccharide (1-6) have been prepared utilising monodeoxy monosaccharide precursors. The reducing end deoxy derivatives were synthesised by N-iodosuccinimide/silver trifluoromethanesulfonate (NIS/AgOTf)-promoted couplings of a common disaccharide thioglycoside donor 10 to suitably protected monodeoxy acceptors 9 and 12, affording trisaccharides, which after deprotection yielded target structures 1 and 2. The non-reducing end deoxy derivatives could similarly be produced by halide-assisted glycosylations of a common disaccharide acceptor 17 with monodeoxy glycosyl bromide donors (obtained from thioglycosides 18 and 20) to yield, after removal of protecting groups, target trisaccharides 3 and 4. The analogues with the deoxy function in the middle mannose residue, were obtained through orthogonal halide-assisted coupling of tetrabenzyl-glucopyranosyl bromide to monodeoxy thioglycoside acceptors to give thioglycoside disaccharides, which subsequently were used as donors in NIS/AgOTf-promoted couplings to a common 2-hydroxy-mannose acceptor 15 to afford trisaccharides; deprotection yielded the final target compounds 5 and 6. (c) 2006 Elsevier Ltd. All rights reserved.