3,5-O-(2-formylbenzylidene)-1,2-O-isopropylidene-α-D-xylofuranose | 337903-22-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3,5-O-(2-formylbenzylidene)-1,2-O-isopropylidene-α-D-xylofuranose
• 英文别名: 2-[(1S,2R,6R,8R,11S)-4,4-dimethyl-3,5,7,10,12-pentaoxatricyclo[6.4.0.02,6]dodecan-11-yl]benzaldehyde
• CAS: 337903-22-7
• 化学式: C₁₆H₁₈O₆
• 分子量: 306.315
• InChiKey: WPIUKIFUPUIEBY-QKGCVVFFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  3,5-O-(2-formylbenzylidene)-1,2-O-isopropylidene-α-D-xylofuranose 在 sodium hydride 、 溶剂黄146 作用下， 以 二甲基亚砜 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 (3S)-3-benzyloxymethyl-1,3-dihydro-1-methoxybenzo[c]furan
  参考文献：
  名称：

  Facile separation of chiral 1,3-dihydrobenzo[ c ]furan derivatives using a d -xylose moiety as a protecting group

  摘要：

  1,2-O-Isopropylidene-alpha -D-xylofuranose has been used to protect one aldehyde group of o-phthalaldehyde. This chiral protecting group acts as a resolving agent and this leads to separable diastereoisomers when a new stereogenic centre is created by the conversion of the second aldehyde group to a benzyloxyhydroxyethyl chain. These separated diastereoisomers were cyclised to 1,3-dihydrobenzo[c]furans with retention of chiral integrity at the C3 site thus allowing further elaboration to enantiomerically pure nucleoside analogues. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00488-2
• 作为产物：
  描述：

  1,2-O-异亚丙基-alpha-D-呋喃木糖 、 邻苯二甲醛 在 对甲苯磺酸 作用下， 以 四氢呋喃 为溶剂， 反应 5.0h， 以49%的产率得到3,5-O-(2-formylbenzylidene)-1,2-O-isopropylidene-α-D-xylofuranose
  参考文献：
  名称：

  Facile separation of chiral 1,3-dihydrobenzo[ c ]furan derivatives using a d -xylose moiety as a protecting group

  摘要：

  1,2-O-Isopropylidene-alpha -D-xylofuranose has been used to protect one aldehyde group of o-phthalaldehyde. This chiral protecting group acts as a resolving agent and this leads to separable diastereoisomers when a new stereogenic centre is created by the conversion of the second aldehyde group to a benzyloxyhydroxyethyl chain. These separated diastereoisomers were cyclised to 1,3-dihydrobenzo[c]furans with retention of chiral integrity at the C3 site thus allowing further elaboration to enantiomerically pure nucleoside analogues. (C) 2001 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0957-4166(00)00488-2

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.