1,3,4,6-tetra-O-benzyl-2,5-anhydro-D-talitol | 113889-69-3

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,3,4,6-tetra-O-benzyl-2,5-anhydro-D-talitol
• 英文别名: (2R,3S,4R,5R)-3,4-bis(phenylmethoxy)-2,5-bis(phenylmethoxymethyl)oxolane
• CAS: 113889-69-3
• 化学式: C₃₄H₃₆O₅
• 分子量: 524.657
• InChiKey: DHVGVYQEYOXUTI-PZMYXVABSA-N

物化性质

• 沸点：
  644.1±55.0 °C(predicted)
• 密度：
  1.18±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.36
• 重原子数：
  39.0
• 可旋转键数：
  14.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  46.15
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为产物：
  描述：

  (2,3,5-tri-O-benzyl-α-D-ribosyl)phenylacetylene 在 Lindlar's catalyst 喹啉 、 sodium tetrahydroborate 、 氢气 、 sodium hydride 、 臭氧 作用下， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 28.0h， 生成 1,3,4,6-tetra-O-benzyl-2,5-anhydro-D-talitol
  参考文献：
  名称：

  Alkynylation of mixed acetals with organotin acetylides

  摘要：

  DOI：

  10.1021/ja00216a025

文献信息

• Stereoselective synthesis of tetrahydrofurans and linear methyl enol-ethers from glycals
  作者：Enzo Bettelli、Piero D'Andrea、Stefano Mascanzoni、Pietro Passacantilli、Giovanni Piancatelli

  DOI：10.1016/s0008-6215(97)10062-3

  日期：1998.1

  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.
• ZHAI, DONGGUAN;ZHAI, WEIXU;WILLIAMS, ROBERT M., J. AMER. CHEM. SOC., 110,(1988) N 8, 2501-2505
  作者：ZHAI, DONGGUAN、ZHAI, WEIXU、WILLIAMS, ROBERT M.

  DOI：——

  日期：——