3,4,6-tri-O-benzyl-2,5-anhydro-D-talitol | 195614-96-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,4,6-tri-O-benzyl-2,5-anhydro-D-talitol
• CAS: 195614-96-1
• 化学式: C₂₇H₃₀O₅
• 分子量: 434.532
• InChiKey: JWIGVHYEQVWIAE-CWTOASCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.13
• 重原子数：
  32.0
• 可旋转键数：
  11.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  57.15
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  3,4,6-tri-O-benzyl-2,5-anhydro-D-talitol 在 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 15.0h， 以75%的产率得到2,5-anhydro-3,4,6-tri-O-benzyl-D-talose
  参考文献：
  名称：

  A Versatile and Highly Selective Hypervalent Iodine (III)/2,2,6,6-Tetramethyl-1-piperidinyloxyl-Mediated Oxidation of Alcohols to Carbonyl Compounds

  摘要：

  Catalytic amounts of 2,2,6,6-tetramethyl-1-piperidinyloxyl (TEMPO) are used in combination with [bis(acetoxy)iodo]benzene (BAIB) as a stoichiometric oxidant in the conversion of primary and secondary alcohols to carbonyl compounds. This procedure works efficiently at room temperature in almost all common solvents and neat in some cases. This process exhibits a very high degree of selectivity for the oxidation of primary alcohols to aldehydes, without any noticeable overoxidation to carboxyl compounds, and a high chemoselectivity in the presence of either secondary alcohols or of other oxidizable moieties. This procedure allows an easy, convenient, high-yielding method for the oxidation of alcohols starting from commercially available compounds.

  DOI：

  10.1021/jo971046m
• 作为产物：
  描述：

  2,5-anhydro-3,4,6-tri-O-benzyl-D-talose 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 0.25h， 以98%的产率得到3,4,6-tri-O-benzyl-2,5-anhydro-D-talitol
  参考文献：
  名称：

  Stereoselective synthesis of tetrahydrofurans and linear methyl enol-ethers from glycals

  摘要：

  The O-benzyl derivatives of 1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (D-glucal, 1), 1,5-anhydro-2,6-dideoxy-L-arabino-hex-1-enitol (L-rhamnal, 7), and I,5-anhydro-2-deoxy-D-lyxo-hex-1-enitol (D-galactal, 9), underwent stereoselectively a ring contraction by treatment with thallium(II:I) nitrate (TTN) in MeOH, giving respectively the dimethylacetal derivatives of 3,4,6-tri-O-benzyl-2,5-anhydro-D-mannose, 3,4-di-O-benzyl-6-deoxy-2,5-anhydro-L-mannose (8) and 3,4,6-tri-O-benzyl-2,5-anhydro-D-talose (10).Conversely, the protected glycals 1, 7 and 9, underwent the ring opening reaction by action of the TTN-NaBH4, reagent in MeOH, providing the enantiomerically pure methyl enol-ethers 3,4,6-tri-O-benzyl-2-deoxy-1-O-methyl-D-arabino-hex-1-enitol, 3,4-di-O-benzyl-2,6-dideoxy-1-O-methyl-L-arabino-hex-1-enitol and 3,4,6-tri-O-benzyl-2-deoxy-1-O-methyl-D-lyxo-hex-1-enitol. The perbenzylated glycosyl-glycals, such as 3,4-di-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-beta-D-glucopyranosyl)-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (cellobial) (16), 3,6-di-O-benzyl-4-O-(2,3,4,6-tetra-O-benzyl-beta-D-galactopyranosyl)-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (lactal) (19) and 3,4-di-O-benzyl-6-O-(2,3,4,6-tetra-O-benzyl-alpha-D-galactopyranosyl)-1,5-anhydro-2-deoxy-D-arabino-hex-1-enitol (melibial) (22), showed the same reactivity as the corresponding glycals by reaction with TTN in MeOH, resulting selectively in the ring contracted compounds at the glycal moiety. The reaction with TTN-NaBH4, in MeOH, carried out on 16, 19 and 22, led to the formation of the open chain derivatives at the glycal site. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0008-6215(97)10062-3