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Synthesis of 2-cyano-2-propyl benzodithioate. Synthesis of 2-cyano-2-propyl benzodithioate Author Joyce Amijs Academy of Technology for Health and Environment Avans Hogeschool, Breda Sonny van Seeters Nishant Sewgobind Abstract Reversible Addition Fragmentation Chain Transfer (RAFT) polymerization is a controlled/living radi cal polymerization. This polymerization method is used for the synthesis of styrene and acrylate block copolymers[1]. The RAFT-agent 2-cyano-2- propyl benzodithioate that is used for this polymerization is very expensive, so it is important to synthesize th e agent and save some cost. It is also important to synthesize the RAFT-agent so it can be used for practical assignments at school, especially for emulsion polymerization. Previous research showed that the yield of the RAFT-agent is less than 1%, so the goal of this study is to optimize the synthesis of RAFT-agent 2-cyano-2-propyl benzodithioate[2]. The synthesis of 2-cyano- 2-propyl benzodithioate is a multiple step reaction and is shown in Figure 1. First dithiobenzoate (2) is synthesized from phenylmagnesiumbromide (1), carbondisulfide and hydrochloric acid. Second bis(thiobenzoyl)disulfide (3) is synthesized according a redox reaction. This step will be optimized and at least it must give a 10% higher yield by using methyl tert - butyl ether and ethanol as solvent instead of ethanol. The RAFT-agent (4) is synthesized with azobisisobutyronitrile and the product of this synthesis will be purified with column chromatography. The products 3 and 4 will be analyzed with UV - Vis spectroscopy, FTIR and LC-MS. Keywords: RAFT-agent, 2-cyano-2-propyl benzodithioate, dithiobenzoate, bis(thiobenzoyl)disulfide Table of content Figure 1. Reaction equation of 2-cyano-2-propyl benzodithioate. [1] M. Hillmyer, „Block copolymer synthesis,” Current opinion in solid state and materials science, vol. 4, nr. 6, pp. 559- 564, 1999. [2] B. Koumba en A. Mayelle, „Design, synthesis and characterization of novel raft agents,” University of stellenbosch, Stellenbosch, 2005. 16
Synthesis for a building block for thiodigalactoside Author Arjan Synthesis de Smit for a building block for thiodigalactoside Academy of Technology for Health and Environment Avans Hogeschool, Breda Universiteit Utrecht Nishant Sewgobind Abstract Multiple galectins have been found in the human body and are involved with biological processes like mitosis and the survival of tumor cells. The 14 different galectins can be divided into three subgroups. The first group has one carbohydrate-recognition domain (CRD). The second group also has a proline and glycine rich fragment and the last group has two CRD’s. Galactin-3 is the only protein that fits into the second subgroup. [1] The goal of this research is to make 3 - O-acetyl-1,2;5,6-di-O-isopropylidene-α-D-gulofuranose from 1,2;5,6-di-O-isopropylidene-α-D-glucofuranose in three synthesis. This product can be used as a building block for a thiodigalactoside that has a strong affinity with galectin -3, but not with the other proteins. It is expected that the conversion rate of each reaction step, shown in the table of content, will be 70% or higher. The first reaction used is an oxidation with pyridinium dichromate. This reaction is followed by an acetylation with pyridine and acetic anhydride. The product is formed after hydrogenation with palladium on carbon. [2] The reactions can be follow with TLC and the intermediates and product can be analysed with FT-IR and NMR after purification with column chromatography. Keywords: Medicinal chemistry, galectins, thiodigalactoside, galectin-3 Table of content Figure 5: Reaction scheme for the synthesis of 1,2;5,6-di-O-isopropylidine-α-D-gulofuranose from 1,2;5,6-di-Oisopropylidene-α-D-glucofuranose. [1] H. van Hattum, H. M. Branderhorst, E. E. Moret, U. J. Nilsson, H. Leffler en R. J. Pieters, „Tuning the Preference of Thiodigalactoside- and Lactosamine-Based Ligands to Galectin-3 over Galectin-1,” Journal of Medicinal Chemistry, vol. 56, nr. 3, pp. 1350-1354, 2013. [2] J. Elhalabi en K. G. Rice, „Synthesis of Uridine 5'-[2-S-Pyridyl-3-thio-alpha-D-galactopyranosyl Diphospate]: Precursors of UDP-Thiogal Sugar Nucleotide Donor Substrate for béta-1,4-Galactosyltransferase,” Nucleosides, Nucleotides & Nucleic Acids, vol. 23, nr1, pp. 195-205, 2004 17
Page 1 and 2: Book of Abstracts Poster presentati
Page 3 and 4: Avans University of Applied Science
Page 5 and 6: Collaborations 5
Page 7 and 8: Preface Dear reader, We present her
Page 9 and 10: Index SPOC1 13 Tutor: Nishant Sewgo
Page 11 and 12: Group index SPOC1 The inhibition of
Page 13 and 14: The inhibition of the Pseudomonas A
Page 15: Synthesis of a surface-active RAFT-
Page 19 and 20: 19
Page 21 and 22: Group index SPOC2 In situ catalysed
Page 23 and 24: Book of abstracts SPOC 2018 3,4-uns
Page 25 and 26: Determination of activation energie
Page 27 and 28: Book of abstracts SPOC 2018 Synthes
Page 29 and 30: Group index SPOC3 Decarboxylation o
Page 31 and 32: Decarboxylation of ferulic acid to
Page 37 and 38: Group index SPOC4 The kinetics of t
Page 39 and 40: The kinetics of the Knoevenagel con
Page 41 and 42: Isolation of catalytic intermediate
Page 43 and 44: Chemical recycling to Oxazolines Au
Page 45 and 46: Group index SPOC5 Molecular Imprint
Page 47 and 48: Taxus extract Molecular Imprinted P
Page 49 and 50: MIP synthesis of 4-vinylpyridine Au
Page 51 and 52: Biobased Block-Copolymers due ATRP
Page 53 and 54: 53
Page 55 and 56: Group index SPOC6 Synthesis of Beta
Page 57 and 58: Synthesis of Beta-lactam in three s
Page 59 and 60: Isoxazoline ring opening by TBAT to
Page 61 and 62: Synthesis of a ligand for a synthet
Page 63 and 64: Group index SPOC7 Synthesis of a te
Page 67 and 68:
Synthesis of a terpyridine ligand f
Page 69 and 70:
Synthesis of peptides for IR foldin
Page 71 and 72:
Peptide synthesis for unravelling p
Page 73 and 74:
Dear reader, Acknowledgement s Afte
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