2,5-anhydro-3,4,6-tri-O-benzyl-D-talose | 122194-15-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2,5-anhydro-3,4,6-tri-O-benzyl-D-talose
• 英文别名: (2S,3S,4S,5R)-3,4-bis(phenylmethoxy)-5-(phenylmethoxymethyl)oxolane-2-carbaldehyde
• CAS: 122194-15-4
• 化学式: C₂₇H₂₈O₅
• 分子量: 432.516
• InChiKey: FHNGZJPNWWCNKW-CWTOASCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  32
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  54
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  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
• 作为产物：
  描述：

  D-三乙酰半乳糖烯 在 水 、 sodium methylate 、 sodium hydride 、 二甲基亚砜 、 三乙胺 、 间氯过氧苯甲酸 作用下， 生成 2,5-anhydro-3,4,6-tri-O-benzyl-D-talose
  参考文献：
  名称：

  缩水甘油醚的苯硒酸酯加合物的氧化环收缩。喜多霉素类似物的合成

  摘要：

  首先用苯硒烯基氯，然后用水和三乙胺处理3,4,6-三-O-苄基-葡萄糖醛（），收率（％）为（）。后者化合物的溶液用米氯过苯甲酸和推定的环收缩醛（）中获得转化成showdomycin类似物（在令人满意的总收率）。3,4,6-三- Ö苄基-galactal（ ）进行类似转化成相应的α- -lyxoside（ ）。

  DOI：

  10.1016/0040-4039(88)85267-5

文献信息

• A Versatile and Highly Selective Hypervalent Iodine (III)/2,2,6,6-Tetramethyl-1-piperidinyloxyl-Mediated Oxidation of Alcohols to Carbonyl Compounds
  作者：Antonella De Mico、Roberto Margarita、Luca Parlanti、Andrea Vescovi、Giovanni Piancatelli

  DOI：10.1021/jo971046m

  日期：1997.10.1

  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.
• Highly stereoselective synthesis of C-vinyl furanosides through acid-catalyzed SN2 inversion at the C-3 position of 1,2-dideoxy-hept-1-enitols
  作者：Hitoshi Tsuchiya、Noriaki Asakura、Yasunori Ikeda、Hidetoshi Yamada

  DOI：10.1016/j.carres.2008.08.017

  日期：2008.11

  A highly stereoselective synthesis of C-vinyl furamosides through the S(N)2 inversion at the C-3 position of the 1,2-dideoxy-hept-1-enitols is disclosed. Treatment of the 1,2-dideoxy-hept-1-enitols with diphenylammonium trifluoromethanesulfonate as the acid catalyst produced the C-vinyl furanosides (3,6-anhydro-1,2-dideoxy-hept-1-enitol derivatives) via a subsequent S(N)2 intramolecular debenzyloxyationcycloetherification reaction at the C-3 position. (C) 2008 Elsevier Ltd. All rights reserved.
• KAYE, ANDREW;REESE, COLIN B.;NEIDLE, STEPHEN, NUCLEOSIDES AND NUCLEOTIDES, 7,(1988) N-6, C. 609-612
  作者：KAYE, ANDREW、REESE, COLIN B.、NEIDLE, STEPHEN

  DOI：——

  日期：——