2H-吡喃,2-(3-丁烯基)-6-(1,1-二甲基乙氧基)四氢-3-(苯基甲氧基)-,(2R,3S,6R)- | 167901-80-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2H-吡喃,2-(3-丁烯基)-6-(1,1-二甲基乙氧基)四氢-3-(苯基甲氧基)-,(2R,3S,6R)-
• 英文名称: tert-butyl 4-O-benzyl-2,3,6,7,8,9-hexadeoxy-α-D-erythro-non-8-enopyranoside
• 英文别名: t-butyl 4-O-benzyl-2,3-dideoxy-α-D-gluco-non-8-enopyranoside；(2R,3S,6R)-2-but-3-enyl-6-[(2-methylpropan-2-yl)oxy]-3-phenylmethoxyoxane
• CAS: 167901-80-6
• 化学式: C₂₀H₃₀O₃
• 分子量: 318.456
• InChiKey: RUPBCMRTTUKPPP-IPMKNSEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  23
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2H-吡喃,2-(3-丁烯基)-6-(1,1-二甲基乙氧基)四氢-3-(苯基甲氧基)-,(2R,3S,6R)- 在 disodium hydrogenphosphate 、 sodium dihydrogenphosphate 、 iodonium(di-γ-collidine) perchlorate 、 sodium hexamethyldisilazane 、 臭氧 、 间氯过氧苯甲酸 、 二苯基膦酸锂 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 6.17h， 生成 (S)-4-Benzyloxy-4-[(2R,5S)-5-((R)-1-iodo-butyl)-tetrahydro-furan-2-yl]-butyraldehyde
  参考文献：
  名称：

  PYRANOSIDE ALKENE TEMPLATES FOR THE SYNTHESIS OF CIS-2,5-DISUBSTITUTED TETRAHYDROFURAN SUBUNITS OF THE ACETOGENINS

  摘要：

  The iodoetherification reaction of t-butyl and trityl glycosides of C6 allylated-2,3-dideoxy-D-erythro- and D-threo-pyranosides was examined as part of a model study aimed at the synthesis of the 2,5-disubstituted tetrahydrofuran subunits found in the acetogenin group of natural products. In general, the t-butyl glycosides gave moderate, and the trityl derivatives, excellent stereoselectivity for the cis THF product.

  DOI：

  10.1081/car-120014903
• 作为产物：
  描述：

  Toluene-4-sulfonic acid (2R,3S,6R)-6-tert-butoxy-3-hydroxy-tetrahydro-pyran-2-ylmethyl ester 在 四甲基乙二胺 、 sodium hydride 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 生成 2H-吡喃,2-(3-丁烯基)-6-(1,1-二甲基乙氧基)四氢-3-(苯基甲氧基)-,(2R,3S,6R)-
  参考文献：
  名称：

  C-6 allylated pyranosides for the synthesis of complex oxygenated tetrahydrofurans

  摘要：

  The iodoetherification of C6 allylated D-pyranosides containing an allylic benzyloxy substituent, and their acyclic 5-hexen-, 1,2,4-triol analogs were performed. Pyranosides of R configuration at the allylic ether gave exclusively a syn,syn-2,5-dialkyi-3-oxy-tetrahydrofuran which is primed for elaboration into several classes of naturally occurring THF's. By comparison, the stereoselectivity for the non-pyranoside derivative was much lower. In the S series, the bias was opposite for the pyranoside vs, the non-pyranoside substrates, but the selectivity in both cases was low. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)00282-2

文献信息

• cis-2,5-Disubstituted tetrahydrofurans from pyranosides: A novel example of remote stereocontrol by the aglycone
  作者：Huiping Zhang、Phyllis Wilson、Weifang Shan、Zheming Ruan、David R. Mootoo

  DOI：10.1016/0040-4039(94)02342-9

  日期：1995.1

  A stereoselective methodology, based on neighboring group participation by the acetal ring oxygen, is described for the preparation of highly functionalizable cis-2,5-disubstituted tetrahydrofurans from C6 alkenyl branched pyranosides.

  描述了一种基于乙缩醛环氧的邻近基团参与的立体选择性方法，用于从C6烯基支链吡喃糖苷制备高度可官能化的cis-2,5-二取代四氢呋喃。
• C-6 allylated pyranosides for the synthesis of complex oxygenated tetrahydrofurans
  作者：Mohindra Seepersaud、Michael Blumenstein、David R. Mootoo

  DOI：10.1016/s0040-4020(97)00282-2

  日期：1997.4

  The iodoetherification of C6 allylated D-pyranosides containing an allylic benzyloxy substituent, and their acyclic 5-hexen-, 1,2,4-triol analogs were performed. Pyranosides of R configuration at the allylic ether gave exclusively a syn,syn-2,5-dialkyi-3-oxy-tetrahydrofuran which is primed for elaboration into several classes of naturally occurring THF's. By comparison, the stereoselectivity for the non-pyranoside derivative was much lower. In the S series, the bias was opposite for the pyranoside vs, the non-pyranoside substrates, but the selectivity in both cases was low. (C) 1997 Elsevier Science Ltd.
• PYRANOSIDE ALKENE TEMPLATES FOR THE SYNTHESIS OF <i>CIS</i>-2,5-DISUBSTITUTED TETRAHYDROFURAN SUBUNITS OF THE ACETOGENINS
  作者：Huiping Zhang、Darrin Dabideen、Galyna Pushchinska、David R. Mootoo

  DOI：10.1081/car-120014903

  日期：2002.1.10

  The iodoetherification reaction of t-butyl and trityl glycosides of C6 allylated-2,3-dideoxy-D-erythro- and D-threo-pyranosides was examined as part of a model study aimed at the synthesis of the 2,5-disubstituted tetrahydrofuran subunits found in the acetogenin group of natural products. In general, the t-butyl glycosides gave moderate, and the trityl derivatives, excellent stereoselectivity for the cis THF product.