1,2-O-(1-methylethylidene)-3-O-allyl-5-C-phenyl-α-D-xylo-furanose | 917358-73-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1,2-O-(1-methylethylidene)-3-O-allyl-5-C-phenyl-α-D-xylo-furanose
• 英文别名: (S)-((3aR,5R,6S,6aR)-6-allyloxy-2,2-dimethyl-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl)(phenyl)methanol；(S)-[(3aR,5R,6S,6aR)-2,2-dimethyl-6-prop-2-enoxy-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]-phenylmethanol
• CAS: 917358-73-7
• 化学式: C₁₇H₂₂O₅
• 分子量: 306.359
• InChiKey: ABZCONPTTKHRCJ-ZVDSWSACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  57.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-O-(1-methylethylidene)-3-O-allyl-5-C-phenyl-α-D-xylo-furanose 在 盐酸 、 4-二甲氨基吡啶 、 正丁基锂 、 四丁基碘化铵 、 sodium hydride 、 三乙胺 、 2,3-二氯-5,6-二氰基-1,4-苯醌 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 74.0h， 生成 2,4-di-O-acetyl-3-O-allyl-5,6-dideoxy-1-C-phenyl-hex-5-enitol
  参考文献：
  名称：

  RCM/PCC oxidation strategy for synthesis of functionalized cyclic α,β-unsaturated lactones: synthesis of (+)-triacetoxygoniotriol and its diastereomers

  摘要：

  A novel methodology leading to the synthesis of (+)-triacetoxygoniotriol 2 from D-glucose is described. Construction of the core six-membered alpha, beta-unsaturated lactone moiety involved ring closing metathesis (RCM) followed by a PCC oxidation. Later exploiting the pseudo-symmetry of D-glucose three other diastereomers of triacetoxygoniotriol were synthesized using the developed methodology. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.016
• 作为产物：
  描述：

  3-O-allyl-1,2-O-isopropylidene-α-D-glucofuranose 在 sodium periodate 、 silica gel 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 20.0h， 生成 1,2-O-(1-methylethylidene)-3-O-allyl-5-C-phenyl-α-D-xylo-furanose
  参考文献：
  名称：

  RCM/PCC oxidation strategy for synthesis of functionalized cyclic α,β-unsaturated lactones: synthesis of (+)-triacetoxygoniotriol and its diastereomers

  摘要：

  A novel methodology leading to the synthesis of (+)-triacetoxygoniotriol 2 from D-glucose is described. Construction of the core six-membered alpha, beta-unsaturated lactone moiety involved ring closing metathesis (RCM) followed by a PCC oxidation. Later exploiting the pseudo-symmetry of D-glucose three other diastereomers of triacetoxygoniotriol were synthesized using the developed methodology. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.09.016

文献信息

• Stereoselective total synthesis of styryl-lactones: (+)-crassalactones B and C, (+)-howiionol A, (+)-tricinnamate, (+)-goniofufurone and (+)-dicinnamoyl goniofufurone
  作者：Gangavaram V.M. Sharma、Samala Mallesham

  DOI：10.1016/j.tetasy.2010.10.016

  日期：2010.11

  The total synthesis of (+)-crassalactone B (+)-crassalactone C (+)-howiionol A (+)-tricinnamate (+)-goniofufurone and (+)-dicinnamoyl goniofufurone is achieved by a chit-on approach starting from diacetone D-glucose (DAG) Mitsunobu inversion Wittig olefination and ring closing metatheses were used as key steps for (+)-howiionol A and (+)-tricinnamate Meldrum s acid was used for the synthesis of (+)-crassalactone C (+)-goniofufurone and (+)-dicinnamoyl goniofufurone Yamaguchi esterification was used for (+)-crassalactone B while a Grignard reaction followed by concomitant deallylation was first reported in the synthesis of (+)-dicinnamoyl goniofufurone (C) 2010 Elsevier Ltd All rights reserved
• RCM/PCC oxidation strategy for synthesis of functionalized cyclic α,β-unsaturated lactones: synthesis of (+)-triacetoxygoniotriol and its diastereomers
  作者：G.S.C. Srikanth、Urlam Murali Krishna、Girish K. Trivedi、John F. Cannon

  DOI：10.1016/j.tet.2006.09.016

  日期：2006.11

  A novel methodology leading to the synthesis of (+)-triacetoxygoniotriol 2 from D-glucose is described. Construction of the core six-membered alpha, beta-unsaturated lactone moiety involved ring closing metathesis (RCM) followed by a PCC oxidation. Later exploiting the pseudo-symmetry of D-glucose three other diastereomers of triacetoxygoniotriol were synthesized using the developed methodology. (c) 2006 Elsevier Ltd. All rights reserved.