135690-95-8

Basic information

• Product Name: Acetic acid, [bis(2,2,2-trifluoroethoxy)phosphinyl]-, phenylmethyl ester
• CAS NO: 135690-95-8
• Molecular Formula: C13H13F6O5P
• Molecular Weight: 394.207
• Mol File: 135690-95-8.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Acetic acid, [bis(2,2,2-trifluoroethoxy)phosphinyl]-, phenylmethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Acetic acid, [bis(2,2,2-trifluoroethoxy)phosphinyl]-, phenylmethyl ester(135690-95-8)
• EPA Substance Registry System: Acetic acid, [bis(2,2,2-trifluoroethoxy)phosphinyl]-, phenylmethyl ester(135690-95-8)

Safety Data

• Hazardous Substances Data: 135690-95-8(Hazardous Substances Data)

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 
• 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 
• 135690-99-2 3-[(S)-1-(tert-Butyl-dimethyl-silanyl)-4-oxo-azetidin-2-yl]-2,3-dihydroxy-propionic 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 
• 135690-56-1 (Z)-3-[(S)-1-(tert-Butyl-dimethyl-silanyl)-4-oxo-azetidin-2-yl]-acrylic acid benzyl 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 

Relevant articles and documents

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

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 Al-77-B

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