D-xylose-(2R,3R,4R)-5-di-O-isopropylidene-[4-(methylphenyl)sulfonyl]hydrazone | 170028-87-2

• 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: D-xylose-(2R,3R,4R)-5-di-O-isopropylidene-[4-(methylphenyl)sulfonyl]hydrazone
• 英文别名: 2,3:4,5-di-O-isopropylidene-D-xylose tosylhydrazone；N-[[(4S,5R)-5-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,2-dimethyl-1,3-dioxolan-4-yl]methylideneamino]-4-methylbenzenesulfonamide
• CAS: 170028-87-2
• 化学式: C₁₈H₂₆N₂O₆S
• 分子量: 398.48
• InChiKey: XSYPMPGPERYIKJ-ARFHVFGLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  27
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  104
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  D-xylose-(2R,3R,4R)-5-di-O-isopropylidene-[4-(methylphenyl)sulfonyl]hydrazone 在 吡啶 、 盐酸 、 sodium azide 、 sodium methylate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 71.5h， 生成 (2S,3R,4E)-2-叠氮-4-十八碳烯-1,3-二醇
  参考文献：
  名称：

  An Efficient Stereoselective Synthesis of Sphingosine

  摘要：

  本文介绍了一种立体可控的 d-(+)-赤藓-鞘氨醇 (1) 合成方法，该方法以 d-木糖为手性池材料，采用 2,3 : 4,5-di-O-isopropylidene-dxylose 的甲苯腙的加成-分裂反应作为链延伸的关键步骤，同时进行反式选择性 C=C 键形成。

  DOI：

  10.1055/s-1998-4482
• 作为产物：
  描述：

  2,3:4,5-di-O-isopropylidene-D-xylose di(p-tolyl) dithioacetal 在 mercury dichloride 、 mercury(II) oxide 作用下， 以 甲醇 、 水 、 丙酮 为溶剂， 反应 12.0h， 生成 D-xylose-(2R,3R,4R)-5-di-O-isopropylidene-[4-(methylphenyl)sulfonyl]hydrazone
  参考文献：
  名称：

  Synthesis of α-l-rhamnosyl ceramide and evaluation of its binding with anti-rhamnose antibodies

  摘要：

  An α-L-rhamnosyl ceramide (1, α-L-RhaCer) has been prepared that was recognized by anti-L-rhamnose (anti-Rha) antibodies. During these studies we explored the use of an α-L-rhamnosyl thioglycoside and a trichloroacetimidate as a glycosyl donors. Subsequently, the acceptors desired for glycosylation, 3-O-benzoylazidosphingosine or 3-O-alloxycarbonylsphingosine, were prepared from D-xylose. The thioglycoside donor, 2,3,4-tri-O-acetyl-1-(4-tolyl)thio-α-L-rhamnopyranoside, and the trichloroacetimidate donor, 2,3,4-tri-O-acetyl-1-(2,2,2-trichloroethanimidate)-α-L-rhamnopyranoside, were synthesized in 50% and 78% yield overall, respectively. The synthesis of the glycosylation acceptor employed an addition-fragmentation olefination that was successfully carried out in 53% yield. With the successful synthesis of key intermediates, α-L-RhaCer (1) was prepared without any insurmountable obstacles. Anti-Rha antibodies were prepared in BALB/c mice by immunizing them with rhamnose-ovalbumin (Rha-Ova) with Sigma Adjuvant System (SAS) and the anti-L-Rha antibodies were isolated from the blood sera. Liposomes and EL4 tumor cells were used as model systems to demonstrate the ability of 1 to insert into a lipid bilayer. The interaction of the liposomes or the EL4 cells with α-L-RhaCer (1) and anti-Rha antibodies were investigated by fluorescence microscopy and flow cytometry, respectively, to confirm the ability of glycolipid 1 to be displayed on the tumor cell surface as well as the ability to be recognized by anti-Rha antibodies.

  DOI：

  10.1016/j.bmc.2014.08.002

文献信息

• Chandrasekhar; Takhi; Yadav, Tetrahedron Letters, 1995, vol. 36, # 28, p. 5071 - 5074
  作者：Chandrasekhar、Takhi、Yadav

  DOI：——

  日期：——
• Synthesis of unusual amino acids: N-(tert-butoxycarbonyl)-l-vinyl glycine and N-(tert-butoxycarbonyl)-l-homophenylalanine
  作者：S. Chandrasekhar、Abbas Raza、Mohamed Takhi

  DOI：10.1016/s0957-4166(02)00120-9

  日期：2002.3

  The synthesis of the unusual amino acids N-(tert-butoxycarbonyl)-L-vinyl glycine and N-(tert-butoxycarbonyl)-L-homophenylalanine starting from commercially available D-xylose via an alkylative fragmentation method is described. (C) 2002 Elsevier Science Ltd. All rights reserved.
• Synthesis of α-l-rhamnosyl ceramide and evaluation of its binding with anti-rhamnose antibodies
  作者：David E. Long、Partha Karmakar、Katherine A. Wall、Steven J. Sucheck

  DOI：10.1016/j.bmc.2014.08.002

  日期：2014.10

  An α-L-rhamnosyl ceramide (1, α-L-RhaCer) has been prepared that was recognized by anti-L-rhamnose (anti-Rha) antibodies. During these studies we explored the use of an α-L-rhamnosyl thioglycoside and a trichloroacetimidate as a glycosyl donors. Subsequently, the acceptors desired for glycosylation, 3-O-benzoylazidosphingosine or 3-O-alloxycarbonylsphingosine, were prepared from D-xylose. The thioglycoside donor, 2,3,4-tri-O-acetyl-1-(4-tolyl)thio-α-L-rhamnopyranoside, and the trichloroacetimidate donor, 2,3,4-tri-O-acetyl-1-(2,2,2-trichloroethanimidate)-α-L-rhamnopyranoside, were synthesized in 50% and 78% yield overall, respectively. The synthesis of the glycosylation acceptor employed an addition-fragmentation olefination that was successfully carried out in 53% yield. With the successful synthesis of key intermediates, α-L-RhaCer (1) was prepared without any insurmountable obstacles. Anti-Rha antibodies were prepared in BALB/c mice by immunizing them with rhamnose-ovalbumin (Rha-Ova) with Sigma Adjuvant System (SAS) and the anti-L-Rha antibodies were isolated from the blood sera. Liposomes and EL4 tumor cells were used as model systems to demonstrate the ability of 1 to insert into a lipid bilayer. The interaction of the liposomes or the EL4 cells with α-L-RhaCer (1) and anti-Rha antibodies were investigated by fluorescence microscopy and flow cytometry, respectively, to confirm the ability of glycolipid 1 to be displayed on the tumor cell surface as well as the ability to be recognized by anti-Rha antibodies.
• An Efficient Stereoselective Synthesis of Sphingosine
  作者：Pradeep Kumar、Richard R. Schmidt

  DOI：10.1055/s-1998-4482

  日期：1998.1

  A stereocontrolled synthesis of d-(+)-erythro-sphingosine (1), starting from d-xylose as chiral pool material and employing the addition-fragmentation reaction of tosyl hydrazone of 2,3 : 4,5-di-O-isopropylidene-d-xylose as key step for the chain extension with concomitant trans-selective C=C bond formation, is described.

  本文介绍了一种立体可控的 d-(+)-赤藓-鞘氨醇 (1) 合成方法，该方法以 d-木糖为手性池材料，采用 2,3 : 4,5-di-O-isopropylidene-dxylose 的甲苯腙的加成-分裂反应作为链延伸的关键步骤，同时进行反式选择性 C=C 键形成。