219913-99-2

Upstream product

• 2491-18-1 (S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride 
• 173251-21-3 (2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienoic acid 
• 173251-18-8 (2R,3E)-2-isopropyl-4-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-3-butenal 
• 173251-17-7 (2R,3E)-2-isopropyl-4-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-3-butenol 
• 173251-19-9 methyl (2E,4R,5R,6E)-4-hydroxy-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienoate 
• 219914-25-7 methyl (2E,4R,5R,6E)-4-(mesyloxy)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienoate 
• 173251-20-2 methyl (2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienoate 
• 6921-34-2 benzylmagnesium chloride 

Downstream Products

• 173251-23-5 (2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienyl methionine 
• 219914-03-1 (2S,3Z,5S,6E,8R)-2-(phenylmethyl)-5-isopropyl-8-amino-9-(carbomethoxysulfenylthio)-2,6-nonadienyl methionine 
• 173251-24-6 (2S,3Z,5S,6E,8R)-2-(phenylmethyl)-5-isopropyl-8-(tert-butyloxycarbonylamino)-9-(carbomethoxysulfenylthio)-2,6-nonadienyl methionine 

Relevant academic research and scientific papers

Synthesis of sulfur-containing olefinic peptide mimetic farnesyl transferase inhibitors using the Nozaki-Hiyama-Kishi reaction and cuprate S(N)2' displacements

Syntheses of the potent sulfur-containing tetrapeptide mimetic farnesyl transferase inhibitors B956 (22) and B957 (23) are described. The two double bonds in 22 and 23 were constructed by application of iterative NHK and cuprate S(N)2' reactions. Normal syn NHK reaction and substrate-dependent syn and anti-S(N)2' diastereoselectivities accompanied by exclusive E-olefin selectivity were observed for the first NHK iteration (1 → 4). In the second iteration, unexpected epimerization and a strong preference for syn diastereoselectivity was observed for the NHK reaction (5b → 7a + 9a) while an unusual Z-olefin was observed for the S(N)2' reaction (7b → 11). Deprotection conditions were optimized to ensure high purity and yield of the final aminothiol compounds.