ethyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-thio-β-D-fructofuranoside | 302905-16-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-thio-β-D-fructofuranoside
• 英文别名: Bn(-3)[TBDPS(-6)]Fruf(b)-SEt；(2R,3R,4S,5S)-2-[[tert-butyl(diphenyl)silyl]oxymethyl]-5-ethylsulfanyl-5-(hydroxymethyl)-4-phenylmethoxyoxolan-3-ol
• CAS: 302905-16-4
• 化学式: C₃₁H₄₀O₅SSi
• 分子量: 552.807
• InChiKey: RZKYSBOUFAXVSO-UWVMXDRVSA-N

物化性质

• 沸点：
  641.3±55.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.35
• 重原子数：
  38
• 可旋转键数：
  12
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  93.4
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ethyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-thio-β-D-fructofuranoside 在 palladium on activated charcoal 咪唑 、 Amberlite IR-45(OH-) 、 di-tert-butylmethylpyridine 、 氢气 、 DMTST 、 tris(dimethylamino)sulfonium trimethylsilyldifluoride 作用下， 以 甲醇 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， -35.0~20.0 ℃ 、758.44 kPa 条件下， 反应 6.0h， 生成 蔗糖
  参考文献：
  名称：

  A Novel β-Directing Fructofuranosyl Donor Concept. Stereospecific Synthesis of Sucrose

  摘要：

  A new concept for the construction of beta-D-fructofuranosides based on the idea of locking the anomeric CH2OH group to the alpha-side through an internal bridge to the 4-hydroxyl group is presented. Thioglycoside fructose donors containing an internal 1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl) (TIPS) acetal bridge have been constructed and used in glycosylations with dimethyl(thiomethyl)sulfonium triflate (DMTST) as promoter. The couplings were stereospecific to give beta-D-fructofuranosyl disaccharides in high yields. Using this approach, sucrose has been synthesized stereospecifically in 80% yield.

  DOI：

  10.1021/ja001439u
• 作为产物：
  描述：

  ethyl 6-O-tert-butyldiphenylsilyl-1-O-(4,4'-dimethoxytriphenyl)methyl-2-thio-β-D-fructofuranoside 在 三乙基硅烷 、 sodium hydroxide 、 四丁基硫酸氢铵 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 122.0h， 生成 ethyl 3-O-benzyl-6-O-tert-butyldiphenylsilyl-2-thio-β-D-fructofuranoside
  参考文献：
  名称：

  A Novel β-Directing Fructofuranosyl Donor Concept. Stereospecific Synthesis of Sucrose

  摘要：

  A new concept for the construction of beta-D-fructofuranosides based on the idea of locking the anomeric CH2OH group to the alpha-side through an internal bridge to the 4-hydroxyl group is presented. Thioglycoside fructose donors containing an internal 1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl) (TIPS) acetal bridge have been constructed and used in glycosylations with dimethyl(thiomethyl)sulfonium triflate (DMTST) as promoter. The couplings were stereospecific to give beta-D-fructofuranosyl disaccharides in high yields. Using this approach, sucrose has been synthesized stereospecifically in 80% yield.

  DOI：

  10.1021/ja001439u

文献信息

• A Novel β-Directing Fructofuranosyl Donor Concept. Stereospecific Synthesis of Sucrose
  作者：Stefan Oscarson、Fernando W. Sehgelmeble

  DOI：10.1021/ja001439u

  日期：2000.9.1

  A new concept for the construction of beta-D-fructofuranosides based on the idea of locking the anomeric CH2OH group to the alpha-side through an internal bridge to the 4-hydroxyl group is presented. Thioglycoside fructose donors containing an internal 1,4-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl) (TIPS) acetal bridge have been constructed and used in glycosylations with dimethyl(thiomethyl)sulfonium triflate (DMTST) as promoter. The couplings were stereospecific to give beta-D-fructofuranosyl disaccharides in high yields. Using this approach, sucrose has been synthesized stereospecifically in 80% yield.