3,5-O-(S)[2-((R)-1,2-dihydroxyethyl)benzylidene]-1,2-O-isopropylidene-α-D-xylofuranose | 446242-24-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 3,5-O-(S)[2-((R)-1,2-dihydroxyethyl)benzylidene]-1,2-O-isopropylidene-α-D-xylofuranose
• 英文别名: 3,5-O-[2-((R)-1,2-dihydroxyethyl)benzylidene]-1,2-O-isopropylidene-α-D-xylofuranose；(1R)-1-[2-[(1S,2R,6R,8R,11S)-4,4-dimethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecan-11-yl]phenyl]ethane-1,2-diol
• CAS: 446242-24-6
• 化学式: C₁₇H₂₂O₇
• 分子量: 338.357
• InChiKey: FWLJFFBBFKOLML-XBORSJSESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  86.6
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  3,5-O-(S)[2-((R)-1,2-dihydroxyethyl)benzylidene]-1,2-O-isopropylidene-α-D-xylofuranose 在 对甲苯磺酸 、 溶剂黄146 、 三乙胺 作用下， 以 水 、 甲苯 为溶剂， 生成 Benzoic acid (R)-3-hydroxy-1,3-dihydro-isobenzofuran-1-ylmethyl ester
  参考文献：
  名称：

  Asymmetric synthesis of (3S) 3-benzoyloxymethylisobenzofuranone and its 3R enantiomer as analogues of α,β-butenolides

  摘要：

  Both enantiomers of 3-benzoyloxymethylisobenzofuranone have been obtained in good yield in six steps from phthalaldehyde using a D-xylose derivative as a chiral protecting group. The two chiral heterocycles are gamma-hydroxymethyl-alpha,beta-butenolide analogues having a benzene ring in positions 2 and 3. The key step was the dihydroxylation using both OsO4 and AD-mix developed by Sharpless. The asymmetric dihydroxylation using AD-mix required a double diastereoselectivity and gave excellent diastereoisomeric excess. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02662-x
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 在 potassium tert-butylate 、 对甲苯磺酸 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 叔丁醇 作用下， 以 水 、 甲苯 为溶剂， 生成 3,5-O-(S)[2-((R)-1,2-dihydroxyethyl)benzylidene]-1,2-O-isopropylidene-α-D-xylofuranose
  参考文献：
  名称：

  Asymmetric synthesis of (3S) 3-benzoyloxymethylisobenzofuranone and its 3R enantiomer as analogues of α,β-butenolides

  摘要：

  Both enantiomers of 3-benzoyloxymethylisobenzofuranone have been obtained in good yield in six steps from phthalaldehyde using a D-xylose derivative as a chiral protecting group. The two chiral heterocycles are gamma-hydroxymethyl-alpha,beta-butenolide analogues having a benzene ring in positions 2 and 3. The key step was the dihydroxylation using both OsO4 and AD-mix developed by Sharpless. The asymmetric dihydroxylation using AD-mix required a double diastereoselectivity and gave excellent diastereoisomeric excess. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)02662-x

文献信息

• On the Origin of the Facial Selectivity of the Sharpless Asymmetric Dihydroxylation of Styrene Derivatives
  作者：Nicolas Moitessier、Christophe Henry、Christophe Len、Denis Postelb、Yves Chapleura

  DOI：10.1081/car-120019011

  日期：2003.1.3

  Xylose/styrene-based substrates were reacted with Sharpless asymmetric dihydroxylation reagents AD-mix alpha and AD-mix beta. Unlike the previously reported xylose allyl ether, the saccharide unit did not affect the stereochemical outcome of the reaction. Asymmetric dihydroxylation using AD-mix alpha or AD-mix beta of the chiral olefin gave mainly one diastereoisomer (de: 98%) with S and R configuration respectively. A modelling study directed at a rationalisation of the asymmetric dihydroxylation data is described and applied to diversely derivatised styrenes.
• Asymmetric synthesis of (3S) 3-benzoyloxymethylisobenzofuranone and its 3R enantiomer as analogues of α,β-butenolides
  作者：Christophe Len、Abdelmajid Sélouane、Asa Weiling、Fabien Coicou、Denis Postel

  DOI：10.1016/s0040-4039(02)02662-x

  日期：2003.1

  Both enantiomers of 3-benzoyloxymethylisobenzofuranone have been obtained in good yield in six steps from phthalaldehyde using a D-xylose derivative as a chiral protecting group. The two chiral heterocycles are gamma-hydroxymethyl-alpha,beta-butenolide analogues having a benzene ring in positions 2 and 3. The key step was the dihydroxylation using both OsO4 and AD-mix developed by Sharpless. The asymmetric dihydroxylation using AD-mix required a double diastereoselectivity and gave excellent diastereoisomeric excess. (C) 2003 Elsevier Science Ltd. All rights reserved.