allyl 3,5-O-(1-methylethylidene)-β-D-xylofuranoside | 96150-77-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 3,5-O-(1-methylethylidene)-β-D-xylofuranoside
• 英文别名: allyl 3,5-O-isopropylidene-β-D-xylofuranoside
• CAS: 96150-77-5
• 化学式: C₁₁H₁₈O₅
• 分子量: 230.261
• InChiKey: LVXOMAJMKNTUBJ-DOLQZWNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.43
• 重原子数：
  16.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.82
• 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：

  allyl 3,5-O-(1-methylethylidene)-β-D-xylofuranoside 在 草酰氯 、 potassium tert-butylate 、 对甲苯磺酸 、 copper(II) sulfate 、 二甲基亚砜 、 三乙胺 作用下， 以 二甲基亚砜 为溶剂， 反应 38.25h， 生成 cis-prop-1-enyl 2,3-O-(1-methylethylidene)-2-C-methyl-β-D-lyxofuranoside
  参考文献：
  名称：

  Convergent synthesis of polyether ionophore antibiotics: the synthesis of the monensin bis(tetrahydrofuran) via the Claisen rearrangement of an ester enolate with a .beta.-leaving group

  摘要：

  DOI：

  10.1021/ja00297a038
• 作为产物：
  描述：

  allyl α,β-D-xylofuranoside 、 丙酮 在 硫酸 、 copper(II) sulfate 作用下， 反应 20.0h， 以44%的产率得到allyl 3,5-O-(1-methylethylidene)-α-D-xylofuranoside
  参考文献：
  名称：

  Positional isomers of thioxylobiose, their synthesis and inducing ability for d-xylan-degrading enzymes in the yeast cryptococcus albidus

  摘要：

  Isomeric S-linked 2-thioxylobiose 10, 3-thioxylobiose 17, and 4-thioxylobiose 19 were conveniently prepared by SN2 displacement of suitable triflylglycoses with the sodium salt of 2,3,4-tri-O-acetyl-1-thio-beta-D-glucopyranose, either in N,N-dimethylformamide, or in oxolan in the presence of a sodium complexing agent. Allyl 3,5-O-isopropylidene-2-O-trifluoromethanesulfonyl-beta-D-lyxofuranoside was a convenient electrophilic precursor for 10, which was smoothly obtained after a short sequence of deprotection involving conversion to the 1-propenyl glycoside. 1,2:5,6-Di-O-isopropylidene-3-O-trifluoromethylsulfonyl-alpha-D-allofuranose and 1,2,3-tri-O-benzoyl-4-O-trifluoromethylsulfonyl-beta-L-arabinopyranose were the respective precursors for 17 and 19. 4-Thioxylobiose has a highly stimulatory effect on the synthesis of enzymes of the xylanolytic system in the yeast Cryptococcus albidus when applied to the cells in the presence of the natural disaccharide inducer (1 --> 4)-beta-D-xylobiose.

  DOI：

  10.1016/s0008-6215(00)90548-2