(2S,3R,5S,6S)-2-(1'-hydroxy-3'-trimethylsilyl-prop-2'-yn-1'-yl)-3-vinyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane | 874385-25-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R,5S,6S)-2-(1'-hydroxy-3'-trimethylsilyl-prop-2'-yn-1'-yl)-3-vinyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane
• 英文别名: (1S)-1-[(2R,3R,5S,6S)-3-ethenyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxan-2-yl]-3-trimethylsilylprop-2-yn-1-ol
• CAS: 874385-25-8
• 化学式: C₁₆H₂₈O₅Si
• 分子量: 328.481
• InChiKey: JXHWYZKFNLIFGO-OTJKEOIZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.92
• 重原子数：
  22
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 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：

  (2S,3R,5S,6S)-2-(1'-hydroxy-3'-trimethylsilyl-prop-2'-yn-1'-yl)-3-vinyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane 在 盐酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 24.5h， 生成 (3R,4S,5S)-Hept-1-en-6-yne-3,4,5-triol
  参考文献：
  名称：

  Synthesis and determination of absolute configuration of tetracetate 4a-carba-d-xylofuranoside

  摘要：

  The synthesis of carbasugar analogue tetracetate 4a-carba-D-xylofuranoside (1) was reported. The new route involved the conversion of D-(-)-tartatic acid into an enyne compound, which was then cyclized via a key ring-closing enyne metathesis to form the key intermediate 1-vinyl cyclopentene 9, which was then stereoselectively converted to our target. The absolute configuration of the en ne was determined by modified Mosher's method, while that of tetracetate 4a-carba-D-xylofuranoside by ROSEY spectroscopy and gamma-gauche effect. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.139
• 作为产物：
  描述：

  (2S,3R,5S,6S)-3-(tert-butyldimethylsilanyloxymethyl)-5,6-dimethoxy-5,6-dimethyl[1,4]dioxane-2-carbaldehyde 在 草酰氯 、 乙基溴化镁 、 四丁基氟化铵 、 sodium hydride 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 5.25h， 生成 (2S,3R,5S,6S)-2-(1'-hydroxy-3'-trimethylsilyl-prop-2'-yn-1'-yl)-3-vinyl-5,6-dimethoxy-5,6-dimethyl-1,4-dioxane
  参考文献：
  名称：

  Synthesis and determination of absolute configuration of tetracetate 4a-carba-d-xylofuranoside

  摘要：

  The synthesis of carbasugar analogue tetracetate 4a-carba-D-xylofuranoside (1) was reported. The new route involved the conversion of D-(-)-tartatic acid into an enyne compound, which was then cyclized via a key ring-closing enyne metathesis to form the key intermediate 1-vinyl cyclopentene 9, which was then stereoselectively converted to our target. The absolute configuration of the en ne was determined by modified Mosher's method, while that of tetracetate 4a-carba-D-xylofuranoside by ROSEY spectroscopy and gamma-gauche effect. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2005.09.139

文献信息

• Synthesis and determination of absolute configuration of tetracetate 4a-carba-d-xylofuranoside
  作者：Zhi Jie Xue、Ping Chen、Shu Ying Peng、Yuan Chao Li

  DOI：10.1016/j.tet.2005.09.139

  日期：2006.1

  The synthesis of carbasugar analogue tetracetate 4a-carba-D-xylofuranoside (1) was reported. The new route involved the conversion of D-(-)-tartatic acid into an enyne compound, which was then cyclized via a key ring-closing enyne metathesis to form the key intermediate 1-vinyl cyclopentene 9, which was then stereoselectively converted to our target. The absolute configuration of the en ne was determined by modified Mosher's method, while that of tetracetate 4a-carba-D-xylofuranoside by ROSEY spectroscopy and gamma-gauche effect. (c) 2005 Elsevier Ltd. All rights reserved.