693790-04-4

Basic information

• Product Name: (S)-4-(tert-butyldiphenylsilanyloxy)-3-(4-methoxybenzyloxy)butyric acid methyl ester
• Synonyms: (S)-4-(tert-butyldiphenylsilanyloxy)-3-(4-methoxybenzyloxy)butyric acid methyl ester
• CAS NO: 693790-04-4
• Molecular Weight: 492.687
• Mol File: 693790-04-4.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (S)-4-(tert-butyldiphenylsilanyloxy)-3-(4-methoxybenzyloxy)butyric acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-(tert-butyldiphenylsilanyloxy)-3-(4-methoxybenzyloxy)butyric acid methyl ester(693790-04-4)
• EPA Substance Registry System: (S)-4-(tert-butyldiphenylsilanyloxy)-3-(4-methoxybenzyloxy)butyric acid methyl ester(693790-04-4)

Safety Data

• Hazardous Substances Data: 693790-04-4(Hazardous Substances Data)

Upstream product

• 124655-05-6 (S)-methyl 4-(tert-butyldiphenylsilyloxy)-3-hydroxybutanoate 
• 617-55-0 dimethyl (S)-malate 
• 90414-36-1 methyl (3S)-3,4-dihydroxybutyrate 
• 58479-61-1 tert-butylchlorodiphenylsilane 

Downstream Products

• 221677-48-1 (3S)-4-[1-(tert-butyl)-1,1-diphenylsilyl]oxy-3-[(4-methoxybenzyl)oxy]butan-1-ol 
• 327027-84-9 (3Z,9E)-(1R,7S,11S,15S,17R)-11-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-15-methyl-13-methylene-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-trien-5-one 
• 327027-81-6 (Z)-4-{(2R,6S)-6-[(2E,7E)-(S)-6-(tert-Butyl-dimethyl-silanyloxy)-11-(tert-butyl-diphenyl-silanyloxy)-10-hydroxy-4-oxo-undeca-2,7-dienyl]-5,6-dihydro-2H-pyran-2-yl}-but-2-enoic acid 
• 327027-83-8 (3Z,9E)-(1R,7S,11S,15R,17R)-11-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-15-methyl-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,19-triene-5,13-dione 
• 327027-80-5 (3Z,9E,14E)-(1R,7S,11R,17S)-11-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,14,19-tetraene-5,13-dione 
• 327027-69-0 (3Z,9E,14E)-(1R,7S,11S,17S)-11-(tert-Butyl-dimethyl-silanyloxy)-7-(tert-butyl-diphenyl-silanyloxymethyl)-6,21-dioxa-bicyclo[15.3.1]henicosa-3,9,14,19-tetraene-5,13-dione 
• 693790-22-6 (3R,5S)-5-{2-[(S)-3-(tert-butyldimethylsilanyloxy)-2-(4-methoxybenzyloxy)propyl]thiazol-4-yl}-3-(2,2,2-trichloro-1,1-dimethylethoxycarbonylamino)hexanoic acid (E)-(S)-4-iodo-1,3-dimethylbut-3-enyl ester 
• 693790-20-4 (3R,5S)-5-{2-[(S)-3-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-propyl]-thiazol-4-yl}-3-((R)-toluene-4-sulfinylamino)-hexanoic acid (E)-(S)-4-iodo-1,3-dimethyl-but-3-enyl ester 
• 693790-44-2 (3R,5S)-5-{2-[(S)-3-(tert-butyldimethylsilanyloxy)-2-hydroxypropyl]thiazol-4-yl}-3-(2,2,2-trichloro-1,1-dimethylethoxycarbonylamino)hexanoic acid (E)-(S)-4-iodo-1,3-dimethylbut-3-enyl ester 
• 693790-42-0 (3R,5S)-3-amino-5-{2-[(S)-3-(tert-butyldimethylsilanyloxy)-2-(4-methoxybenzyloxy)propyl]thiazol-4-yl}hexanoic acid (E)-(S)-4-iodo-1,3-dimethylbut-3-enyl ester 
• 693790-17-9 4-Methyl-benzenesulfinic acid [(S)-3-{2-[(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-propyl]-thiazol-4-yl}-but-(E)-ylidene]-amide 
• 693790-49-7 4-[2-(tert-butyl-dimethyl-silanyloxy)-1-methyl-ethyl]-2-[3-(tert-butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-propyl]-4,5-dihydro-thiazol-4-ol 
• 693790-13-5 4-[(R)-2-(tert-butyldimethylsilanyloxy)-1-methylethyl]-2-[(S)-3-(tert-butyldiphenylsilanyloxy)-2-(4-methoxybenzyloxy)propyl]thiazole 
• 693790-51-1 methanesulfonic acid (R)-2-{2-[(S)-3-(tert-butyldiphenylsilanyloxy)-2-(4-methoxybenzyloxy)propyl]thiazol-4-yl}propyl ester 

Relevant articles and documents

Towards EPC-syntheses of the structural class of cochleamycins and macquarimicins. Part 3: EPC-syntheses of the β-keto lactone subunits and first attempts towards the syntheses of the pentacyclic antibiotics of this group

Practical EPC-syntheses of δ-substituted-β-keto δ-lactones, subunits of the cochleamycins and macquarimicins, are presented. In consequence Tietze's tandem reaction is employed to combine δ-allyl-β-keto δ-lactone with a hydrindene derivative, the second subunit of these acetogenic antibiotics. Model reactions for the final oxidative radical tandem cyclization reveal that the electrophilic radical cyclizes exclusively in exo-trig fashion. However, with the intended precursor of macquarimicin C allylic hydrogen abstraction thwarted the oxidative radical tandem cyclization.

Synthesis of the macrocyclic core of laulimalide

equation presented A stereoselective synthesis of 3, corresponding to the fully functionalized macrocyclic core of the novel microtubule-stabilizing agent, laulimalide, has been completed. Efficient macrolactonization was achieved by a Mitsunobu reaction,