1-allyl-2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-α-D-mannopyranose | 1072522-90-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-allyl-2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-α-D-mannopyranose
• 英文别名: 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-allyl-α-D-mannopyranose；(2R,4aR,6R,7R,8R,8aR)-2-phenyl-7,8-bis(phenylmethoxy)-6-prop-2-enyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxine
• CAS: 1072522-90-7
• 化学式: C₃₀H₃₂O₅
• 分子量: 472.581
• InChiKey: YQSPODVILTXYQP-VHNXJUCRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.1
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  46.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  烯丙基三丁基锡 、 2,3-双-O-(苯基甲基)-4,6-O-[(R)-苯基亚甲基]-1-硫代- a-D--吡喃甘露糖苷苯酯 在 1,1'-偶氮(氰基环己烷) 作用下， 以 甲苯 为溶剂， 反应 11.0h， 以67%的产率得到1-allyl-2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-α-D-mannopyranose
  参考文献：
  名称：

  Influence of the O3 Protecting Group on Stereoselectivity in the Preparation of C-Mannopyranosides with 4,6-O-Benzylidene Protected Donors

  摘要：

  alpha-C-Glucopyranosides and mannopyranosides are obtained in 65-85% yields from 4,6-O-benzylidene-protected glucosyl and mannosyl thioglycosides bearing ester functionality at the 3-O-position by a coupling reaction with C-nucleophiles on activation with diphenyl sulfoxide, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride.

  DOI：

  10.1021/jo101453y

文献信息

• Is Donor−Acceptor Hydrogen Bonding Necessary for 4,6-<i>O</i>-Benzylidene-directed β-Mannopyranosylation? Stereoselective Synthesis of β-<i>C</i>-Mannopyranosides and α-<i>C</i>-Glucopyranosides
  作者：David Crich、Indrajeet Sharma

  DOI：10.1021/ol8017038

  日期：2008.11.6

  2,3-Di-O-benzyl-4,6-O-benzylidene-thiohexopyranosides, on activation with 1-benzenesulfinyl piperidine and triflic anhydride, react with allyl silanes and stannanes, and with silyl enolethers to give C-glycosides. In the mannose series the beta-isomers are formed selectively whereas the glucose series provides the (alpha-anomers. This selectivity pattern parallels that of O-glycoside formation and eliminates the need to consider donor-acceptor hydrogen bonding in the formation of the O-glycoside.
• Mild Cu(OTf)₂-Mediated C-Glycosylation with Chelation-Assisted Picolinate as a Leaving Group
  作者：Wenjing Ye、Christopher M. Stevens、Peng Wen、Christopher J. Simmons、Weiping Tang

  DOI：10.1021/acs.joc.0c01041

  日期：2020.12.18

  C-glycosylation reactions of glycosyl picolinates with allyltrimethylsilane or silyl enol ethers were devel-oped. Picolinate as a chelation-assisted leaving group could be activated by Cu(OTf)2 and avoided the use of harsh Lewis acids. The glycosylations were operated under mild neutral conditions and gave the corre-sponding C-glycosides in up to 95% yield with moderate to excellent stereoselectivities.
• Influence of the O3 Protecting Group on Stereoselectivity in the Preparation of <i>C</i>-Mannopyranosides with 4,6-<i>O</i>-Benzylidene Protected Donors
  作者：David Crich、Indrajeet Sharma

  DOI：10.1021/jo101453y

  日期：2010.12.17

  alpha-C-Glucopyranosides and mannopyranosides are obtained in 65-85% yields from 4,6-O-benzylidene-protected glucosyl and mannosyl thioglycosides bearing ester functionality at the 3-O-position by a coupling reaction with C-nucleophiles on activation with diphenyl sulfoxide, 2,4,6-tri-tert-butylpyrimidine, and trifluoromethanesulfonic anhydride.