allyl 2,3,6-tri-O-benzyl-4-O-(trifluoromethylsulfonyl)-α-D-galactopyranoside | 167646-21-1

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: allyl 2,3,6-tri-O-benzyl-4-O-(trifluoromethylsulfonyl)-α-D-galactopyranoside
• 英文别名: allyl 2,3,6-tri-O-benzyl-4-O-trifluoromethylsulfonyl-α-D-galactopyranoside；allyl 2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-α-D-galactopyranoside；Bn(-2)[Bn(-3)][Tf(-4)][Bn(-6)]Gal(a)-O-allyl；[(2R,3S,4R,5R,6S)-4,5-bis(phenylmethoxy)-2-(phenylmethoxymethyl)-6-prop-2-enoxyoxan-3-yl] trifluoromethanesulfonate
• CAS: 167646-21-1
• 化学式: C₃₁H₃₃F₃O₈S
• 分子量: 622.659
• InChiKey: YRLJZHHXLFVRJA-QBHLCAJUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  43
• 可旋转键数：
  15
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  97.9
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  allyl 2,3,6-tri-O-benzyl-4-O-(trifluoromethylsulfonyl)-α-D-galactopyranoside 在 三(二甲氨基)锍二氟三甲基硅酸 作用下， 以 二氯甲烷 为溶剂， 反应 0.33h， 以436 mg的产率得到allyl 4-deoxy-4-fluoro-2,3,6-tri-O-benzyl α-D-galactopyranoside
  参考文献：
  名称：

  Synthesis of 2-fluoro and 4-fluoro galactopyranosyl phosphonate analogues of UDP-Gal

  摘要：

  Two novel nonisosteric UDP-Gal analogues, (2-deoxy-2-fluoro- and 4-deoxy-4-fluoro-alpha-D-galactopyranosyl) phosphonoyl phosphates, were synthesized by optimized multistep procedures starting from 3,4,6-tri-O-benzyl-D-galactal and allyl 2,3,6-tri-O-benzyl-alpha-D-glucopyranoside, respectively. The key steps were a Michaelis-Arbuzov reaction of respective deoxy-fluoro-D-galactopyranosyl acetate with triethyl phosphite followed by a Moffatt-Khorana coupling reaction with UMP-morpholidate. The structure of all new compounds was confirmed by NMR and mass spectroscopies. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2012.07.015
• 作为产物：
  描述：

  allyl 2,3,6-tri-O-benzyl-α-D-galactopyranoside 、 三氟甲磺酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 以96%的产率得到allyl 2,3,6-tri-O-benzyl-4-O-(trifluoromethylsulfonyl)-α-D-galactopyranoside
  参考文献：
  名称：

  多糖的寡糖类似物。第1部分。单糖衍生单体的概念和合成

  摘要：

  建议通过与一系列系统修饰的寡糖类似物（其中一些或所有糖苷O原子被buta-1,3-diyne取代）进行比较，研究残基间H键对多糖结构和性质的影响。 -1，4-二基。该基团足够长以中断残基间的氢键，在化学上是多用途的，并允许二项式合成。描述了制备纤维素类似物所需的最简单单体单元的几种方法。在第一种方法中，通过2和三苄基醚3将烯丙基α-D-吡喃半乳糖苷（1）转化为三氟甲磺酸酯4（方案2）。被氰化物取代（5–7），然后用DIBAH还原，可高产率生成醛9，按照Corey-Fuchs程序（方案3）将其转化为二溴烯烃10和炔烃11。炔烃经12脱保护或直接与半缩醛13脱保护。氧化至内酯14，然后添加三甲基甲硅烷基乙炔酸锂Me 3 SiCCLi / CeCl 3（15）和还原性脱羟基，得到二甲苯二炔16。转化所需的大量Pd催化剂11 13通过将二溴代烯烃10（17 18）脱醛，随后氧化为内酯19，将Me 3

  DOI：

  10.1002/hlca.19950780122

文献信息

• Oligosaccharide Analogues of Polysaccharides. Part 1. Concept and synthesis of monosaccharide-derived monomers
  作者：Jawad Alzeer、Chengzhi Cai、Andrea Vasella

  DOI：10.1002/hlca.19950780122

  日期：1995.2.8

  properties of polysaccharides by comparing them to a series of systematically modified oligosaccharide analogues where some or all of the glycosidic O-atoms are replaced by buta-1,3-diyne-1,4-diyl groups. This group is long enough to interrupt the interresidue H-bonds, is chemically versatile, and allows a binomial synthesis. Several approaches to the simplest monomeric unit required to make analogues of cellulose

  建议通过与一系列系统修饰的寡糖类似物（其中一些或所有糖苷O原子被buta-1,3-diyne取代）进行比较，研究残基间H键对多糖结构和性质的影响。 -1，4-二基。该基团足够长以中断残基间的氢键，在化学上是多用途的，并允许二项式合成。描述了制备纤维素类似物所需的最简单单体单元的几种方法。在第一种方法中，通过2和三苄基醚3将烯丙基α-D-吡喃半乳糖苷（1）转化为三氟甲磺酸酯4（方案2）。被氰化物取代（5–7），然后用DIBAH还原，可高产率生成醛9，按照Corey-Fuchs程序（方案3）将其转化为二溴烯烃10和炔烃11。炔烃经12脱保护或直接与半缩醛13脱保护。氧化至内酯14，然后添加三甲基甲硅烷基乙炔酸锂Me 3 SiCCLi / CeCl 3（15）和还原性脱羟基，得到二甲苯二炔16。转化所需的大量Pd催化剂11 13通过将二溴代烯烃10（17 18）脱醛，随后氧化为内酯19，将Me 3
• Synthesis of 2-fluoro and 4-fluoro galactopyranosyl phosphonate analogues of UDP-Gal
  作者：Irekhjargal Jambal、Karel Kefurt、Martina Hlaváčková、Jitka Moravcová

  DOI：10.1016/j.carres.2012.07.015

  日期：2012.10

  Two novel nonisosteric UDP-Gal analogues, (2-deoxy-2-fluoro- and 4-deoxy-4-fluoro-alpha-D-galactopyranosyl) phosphonoyl phosphates, were synthesized by optimized multistep procedures starting from 3,4,6-tri-O-benzyl-D-galactal and allyl 2,3,6-tri-O-benzyl-alpha-D-glucopyranoside, respectively. The key steps were a Michaelis-Arbuzov reaction of respective deoxy-fluoro-D-galactopyranosyl acetate with triethyl phosphite followed by a Moffatt-Khorana coupling reaction with UMP-morpholidate. The structure of all new compounds was confirmed by NMR and mass spectroscopies. (C) 2012 Elsevier Ltd. All rights reserved.
• Highly efficient synthesis of 1-thioglycosides in solution and solid phase using iminophosphorane bases
  作者：Weizheng Xu、Shawn A. Springfield、John T. Koh

  DOI：10.1016/s0008-6215(99)00327-4

  日期：2000.4

  Disaccharides of l-thioglycosides, an important class of glycomimics, can be synthesized by direct S-alkylation in exceptionally high yields when iminophosphorane bases are employed. The reaction conditions employed appear to be general and stereospecific. Axial and equatorial 4-triflates and primary tosylates of alkyl pyranosides provided excellent yields of thio-disaccharides without substantial elimination products. The iminophosphorane bases also proved to be useful in solid support-bound couplings of thioglycosides though with lower efficiency. (C) 2000 Elsevier Science Ltd. All rights reserved.