3,4-O-benzylidene-2-O-tert-butyldimethylsilyl-D-ribono-1,5-lactone | 473596-05-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氧吡喃
• 英文名称: 3,4-O-benzylidene-2-O-tert-butyldimethylsilyl-D-ribono-1,5-lactone
• 英文别名: (3aR,7R,7aR)-7-[tert-butyl(dimethyl)silyl]oxy-2-phenyl-3a,4,7,7a-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-one
• CAS: 473596-05-3
• 化学式: C₁₈H₂₆O₅Si
• 分子量: 350.487
• InChiKey: ZLOAZUPULDCOJW-BOEXNKMNSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.42
• 重原子数：
  24
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 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：

  3,4-O-benzylidene-2-O-tert-butyldimethylsilyl-D-ribono-1,5-lactone 在 palladium on activated charcoal 吡啶 、 氢气 作用下， 以 乙酸乙酯 为溶剂， 反应 8.0h， 生成 Acetic acid (2R,3R,4R)-2-acetoxymethyl-4-(tert-butyl-dimethyl-silanyloxy)-5-oxo-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Synthesis of differentially protected ribitol derivatives from 3,4-O-benzylidene-d-ribono-1,5-lactone

  摘要：

  Several differentially protected ribitol derivatives were synthesised using 3,4-O-benzylidene-D-ribono-1,5-lactone as versatile starting compounds for oligosaccharide synthesis. The obtained ribitol derivatives allow the regiospecific coupling of glycosyl donors to either of the hydroxyl groups of ribitol and can be applied for the preparation of polyhydroxylated compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.12.008
• 作为产物：
  描述：

  D-(+)-核糖酸-1,4-内酯 在 吡啶 、 盐酸 、 4-二甲氨基吡啶 作用下， 反应 52.0h， 生成 3,4-O-benzylidene-2-O-tert-butyldimethylsilyl-D-ribono-1,5-lactone
  参考文献：
  名称：

  Synthesis of differentially protected ribitol derivatives from 3,4-O-benzylidene-d-ribono-1,5-lactone

  摘要：

  Several differentially protected ribitol derivatives were synthesised using 3,4-O-benzylidene-D-ribono-1,5-lactone as versatile starting compounds for oligosaccharide synthesis. The obtained ribitol derivatives allow the regiospecific coupling of glycosyl donors to either of the hydroxyl groups of ribitol and can be applied for the preparation of polyhydroxylated compounds. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2004.12.008

文献信息

• Reduction of sugar lactones to hemiacetals with lithium triethylborohydride
  作者：Cesar Gonzalez、Sam Kavoosi、Andersson Sanchez、Stanislaw F. Wnuk

  DOI：10.1016/j.carres.2016.06.002

  日期：2016.9

  ribono-1,4-lactones and gulono-1,4-lactone as well as ribono-1,5-lactone and glucono-1,5-lactones with LTBH (1.2 equiv.) in CH2Cl2 at 0 degrees C for 30 min provided the corresponding pentose or hexose hemiacetals in high yields. Commonly used in carbohydrate chemistry protecting groups such as trityl, benzyl, silyl, acetals and to some extent acyls are compatible with this reduction.

  在0°C下于30°C的条件下在CH2Cl2中用LTBH（1.2当量）还原1,4-内酯和1,4-内酯和1,5-内酯和1,5-葡糖苷以及1,5-内酯。 min提供高产率的相应戊糖或己糖半缩醛。通常在碳水化合物化学中使用的保护基如三苯甲基，苄基，甲硅烷基，乙缩醛和一定程度上的酰基与该还原反应相容。
• Efficient and chemoselective cleavage of TBS ethers by a sub-stoichiometric amount of decaborane
  作者：Yeon Joo Jeong、Ji Hee Lee、Eun Soo Park、Cheol Min Yoon

  DOI：10.1039/b201794f

  日期：2002.5.10

  TBS ethers of aliphatic alcohols in THF–MeOH (or methanol) were deprotected chemoselectively to the corresponding alcohols using a sub-stoichiometric amount of decaborane at rt under nitrogen in high yields.

  在氮气下，使用亚化学计量的十硼烷，在室温下选择性去保护碳氢醇的TBS醚，获得相应的醇，产率较高，溶剂为THF-甲醇（或甲醇）。