173251-24-6

Basic information

• Product Name: (2S,3Z,5S,6E,8R)-2-(phenylmethyl)-5-isopropyl-8-(tert-butyloxycarbonylamino)-9-(carbomethoxysulfenylthio)-2,6-nonadienyl methionine
• Synonyms: (2S,3Z,5S,6E,8R)-2-(phenylmethyl)-5-isopropyl-8-(tert-butyloxycarbonylamino)-9-(carbomethoxysulfenylthio)-2,6-nonadienyl methionine
• CAS NO: 173251-24-6
• Molecular Weight: 654.913
• Mol File: 173251-24-6.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: (2S,3Z,5S,6E,8R)-2-(phenylmethyl)-5-isopropyl-8-(tert-butyloxycarbonylamino)-9-(carbomethoxysulfenylthio)-2,6-nonadienyl methionine(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3Z,5S,6E,8R)-2-(phenylmethyl)-5-isopropyl-8-(tert-butyloxycarbonylamino)-9-(carbomethoxysulfenylthio)-2,6-nonadienyl methionine(173251-24-6)
• EPA Substance Registry System: (2S,3Z,5S,6E,8R)-2-(phenylmethyl)-5-isopropyl-8-(tert-butyloxycarbonylamino)-9-(carbomethoxysulfenylthio)-2,6-nonadienyl methionine(173251-24-6)

Safety Data

• Hazardous Substances Data: 173251-24-6(Hazardous Substances Data)

Upstream product

• 6921-34-2 benzylmagnesium chloride 
• 219913-99-2 methyl (2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienyl methionine 
• 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 
• 173251-20-2 methyl (2S,3Z,5S,6E)-2-(phenylmethyl)-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienoate 
• 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 
• 173251-19-9 methyl (2E,4R,5R,6E)-4-hydroxy-5-isopropyl-7-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-2,6-heptadienoate 
• 173251-17-7 (2R,3E)-2-isopropyl-4-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-3-butenol 
• 173251-18-8 (2R,3E)-2-isopropyl-4-<(5R)-N-<(tert-butyloxy)carbonyl>-2,2-dimethyl-4-thiazolidinyl>-3-butenal 
• 26555-40-8 metgoxycarbonylsulfenyl chloride 
• 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 

Downstream Products

• 219914-03-1 (2S,3Z,5S,6E,8R)-2-(phenylmethyl)-5-isopropyl-8-amino-9-(carbomethoxysulfenylthio)-2,6-nonadienyl methionine 

Relevant articles and documents

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.