127462-55-9

Basic information

• Product Name: (E)-(3S,6R,9S,12S,16R,18S)-6-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-3,7,9,12,14,16,18-heptamethyl-1-oxa-4,7,10-triaza-cyclooctadec-14-ene-2,5,8,11-tetraone
• Synonyms: (E)-(3S,6R,9S,12S,16R,18S)-6-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-3,7,9,12,14,16,18-heptamethyl-1-oxa-4,7,10-triaza-cyclooctadec-14-ene-2,5,8,11-tetraone
• CAS NO: 127462-55-9
• Molecular Weight: 755.809
• Mol File: 127462-55-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (E)-(3S,6R,9S,12S,16R,18S)-6-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-3,7,9,12,14,16,18-heptamethyl-1-oxa-4,7,10-triaza-cyclooctadec-14-ene-2,5,8,11-tetraone(CAS DataBase Reference)
• NIST Chemistry Reference: (E)-(3S,6R,9S,12S,16R,18S)-6-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-3,7,9,12,14,16,18-heptamethyl-1-oxa-4,7,10-triaza-cyclooctadec-14-ene-2,5,8,11-tetraone(127462-55-9)
• EPA Substance Registry System: (E)-(3S,6R,9S,12S,16R,18S)-6-[4-(tert-Butyl-dimethyl-silanyloxy)-3-iodo-benzyl]-3,7,9,12,14,16,18-heptamethyl-1-oxa-4,7,10-triaza-cyclooctadec-14-ene-2,5,8,11-tetraone(127462-55-9)

Safety Data

• Hazardous Substances Data: 127462-55-9(Hazardous Substances Data)

Upstream product

• 117289-84-6 (E)-(2S,6R,8S)-8-{[tert-butyl(dimethyl)silyl]oxy}-2,4,6-trimethylnon-4-enoic acid 
• 127462-46-8 2-<(1'R,3'S)-3'-hydroxy-1'-methyl>butyl-1,3-dithiane 
• 117289-82-4 6-(tert-Butyl-dimethyl-silanyloxy)-2,4-dimethyl-hept-1-en-3-ol 
• 117405-40-0 (3S,4R,6S)-6-tert-butyldimethylsiloxy-3-hydroxy-2,4-dimethyl-1-heptene 
• 156659-89-1 (2R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-2-methyl-pentanenitrile 
• 72345-23-4 (2S,4S)-pentane-2,4-diol 
• 156706-65-9 (E)-(2S,6R,8S)-8-((S)-2-{(R)-2-[((S)-2-tert-Butoxycarbonylamino-propionyl)-methyl-amino]-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-phenyl]-propionylamino}-propionyloxy)-2,4,6-trimethyl-non-4-enoic acid 4-methoxy-benzyl ester 
• 156706-61-5 (S)-2-{(R)-2-[((S)-2-tert-Butoxycarbonylamino-propionyl)-methyl-amino]-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-phenyl]-propionylamino}-propionic acid 2,2,2-trichloro-ethyl ester 
• 156706-59-1 (S)-2-{(R)-2-[((S)-2-tert-Butoxycarbonylamino-propionyl)-methyl-amino]-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionylamino}-propionic acid 2,2,2-trichloro-ethyl ester 
• 156706-63-7 (S)-2-{(R)-2-[((S)-2-tert-Butoxycarbonylamino-propionyl)-methyl-amino]-3-[4-(tert-butyl-dimethyl-silanyloxy)-3-iodo-phenyl]-propionylamino}-propionic acid 
• 156706-57-9 (S)-2-{(R)-2-(tert-Butoxycarbonyl-methyl-amino)-3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-propionylamino}-propionic acid 2,2,2-trichloro-ethyl ester 
• 18162-48-6 tert-butyldimethylsilyl chloride 
• 119706-75-1 (R)-2-(tert-butoxycarbonylamino)-3-(4-((tert-butyldimethylsilyl)oxy)phenyl)propanoic acid 
• 119706-71-7 N-(tert-butoxycarbonyl)-O-[tert-butyl(dimethyl)silyl]-N-methyl-D-tyrosine 

Downstream Products

• 108675-63-4 geodiamolide A 

Relevant articles and documents

An expeditious synthesis of geodiamolide a, an 18-membered cytotoxic depsipeptide from marine sponges

Geodiamolide A (1) has been efficiently synthesized from the polypropionate and tripeptide units using the Evans asymmetric alkylation, the Mitsunobu esterification, and the macrolactamization with diphenyl phosphorazidate (DPPA) as key steps. Efficient esterification between the complex polyketide and tripeptide units was also realized under high pressure conditions.

A TOTAL SYNTHESIS OF (+)-GEODIAMOLIDES A AND B, THE NOVEL CYCLODEPSIPEPTIDES

Diastereo-controlled total synthesis of (+)-geodiamolides A (1) and B (2) has been accomplished via a prior synthesis of the tetrapropionate-derived fragment 7 and of the halogenated N-methyltyrosyltripeptide 6, the latter involving direct halogenation of the tripeptide 5, and subsequent coupling of both fragments followed by the trichlorobenzoyl chloride-mediated macrolactonization, respectively.