135690-95-8

Upstream product

• 757-95-9 bis(2,2,2-trifluoroethyl)(methyl)phosphonate 
• 501-53-1 benzyl chloroformate 
• 92466-70-1 bis(2,2,2-trifluoroethyl)phosphite 
• 5437-45-6 Benzyl bromoacetate 

Downstream Products

• 135690-56-1 (4S,1'Z)-1-tert-Butyldimethylsilyl-4-(2-benzyloxycarbonylethenyl)azetidin-2-one 
• 135690-99-2 3-[(S)-1-(tert-Butyl-dimethyl-silanyl)-4-oxo-azetidin-2-yl]-2,3-dihydroxy-propionic acid benzyl ester 
• 135691-01-9 5-[(S)-1-(tert-Butyl-dimethyl-silanyl)-4-oxo-azetidin-2-yl]-2,2-dimethyl-[1,3]dioxolane-4-carboxylic acid benzyl ester 
• 312695-84-4 [bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-acetic acid 7-{3-[6-(2-hydroxy-ethyl)-3,6-dihydro-2H-pyran-2-yl]-2-methyl-propyl}-1-[1-(4-methoxy-benzyloxy)-3-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-5-methoxymethoxy-octa-3,7-dienyl ester 
• 312695-95-7 [bis-(2,2,2-trifluoro-ethoxy)-phosphoryl]-acetic acid 1-[1-(4-methoxy-benzyloxy)-3-(4-methyl-3,6-dihydro-2H-pyran-2-yl)-allyl]-5-methoxymethoxy-7-{2-methyl-3-[6-(2-oxo-ethyl)-3,6-dihydro-2H-pyran-2-yl]-propyl}-octa-3,7-dienyl ester 
• 135690-56-1 (Z)-3-[(S)-1-(tert-Butyl-dimethyl-silanyl)-4-oxo-azetidin-2-yl]-acrylic acid benzyl ester 

Relevant academic research and scientific papers

An improved procedure for the preparation of [Bis(2,2,2-trifluoroethyl) phosphono]acetic acid

A different and improved procedure for the preparation of [bis(2,2,2-trifluoroethyl)phosphono]acetic acid in just one step from bis(2,2,2-trifluoroethyl) phosphonate is described. The protocol employs a Michaelis-Becker reaction between commercially avail

LAULIMALIDE ANALOGS AND USES THEREOF

The present invention provides compounds having formula 1: (I) and pharmaceutically acceptable derivatives thereof, wherein R1-R10, q, t, X0, X1, A, B, D, E, G, J, K, L, M and Z are as described generally and in classes and subclasses herein, and additionally provides pharmaceutical compositions thereof, and methods for the use thereof for the treatment of disorders associated with cellular hyperproliferation.

Total synthesis of microtubule-stabilizing agent (-)-laulimalide

An enantioselective first total synthesis of laulimalide (1) is described. Laulimalide, a remarkably potent antitumor macrolide, has been isolated from the Indonesian sponge Hyattella sp. and the Okinawan sponge Fasciospongia rimosa. Laulimalide represents a new class of antitumor agents with significant clinical potential. The synthesis is convergent and involved the assembly of C3-C16 segment 4 and C17-C28 segment 5 by Julia olefination. The sensitive C2-C3 cis-olefin functionality was installed by Yamaguchi macrolactonization of a hydroxy alkynic acid followed by hydrogenation of the resulting alkynoic lactone over Lindlar's catalyst. Initial attempts of intramolecular Still's variant of Horner - Emmons olefination between the C19-phosphonocetate and C3-aldehyde provided a 1:2 mixture of cis- and trans-macrolactones. The trans-isomer was photo-isomerized to a mixture of cis- and trans-isomers. The other key steps involved ring-closing olefin metathesis to construct both dihydropyran units, stereoselective anomeric alkylation to functionalize the dihydropyran ring, stereoselective reduction of the resulting alkynyl ketone to set the C20-hydroxyl stereochemistry, and a novel Julia olefination protocol for the installation of the C13-exomethylene unit. The sensitive epoxide at C16-C17 was introduced in a highly stereoselective manner by Sharpless epoxidation at the final stage of the synthesis.

Total synthesis of AI-77-B: Stereoselective hydroxylation of 4-alkenylazetidinones

A stereoselective synthesis of the anti-ulcer compound AI-77-B 1 is described. The 4-formylazetidinone 6 was converted into the 4-(Z)-alkene 23 using a phosphonate condensation, and dihydroxylation using osmium tetroxide and N-methylmorpholine W-oxide gav

Total Synthesis of Al-77-B

Stereoselective hydroxylation of the β-lactam ester 8 is a key step in a total synthesis of Al-77-B 1.