2-Chloromethyl-4-nitrophenyl

The preparation of phosphate esters has been reviewed and full details have appeared of the use of 2-chloromethyl-4-nitrophenyl esters (reported last year) in the synthesis of monoesters and mixed dialkyl esters of phosphoric acid. 

PHOSPHORYLATION 2-Chloromethyl-4-nitrophenyl phosphorochloridate. o-Phenyl-ene phosphorochloridate. Phosphoryl chloride. Phosphoryl chloride-Trimethyl phosphate. 

Phenyl a-D- and (3-L- glucopyranosides and their acetates (102 1-7) were prepared and hydrolyzed by yeast (X-glucosidase [104]. 2-Chloromethyl-4-nitrophenyl a-D-glucopyranoside (102 1) showed the most potent inhibitory activity in this series. The 2-chloromethyl-phenyl derivative (102 6) which had no nitro group in the benzene ring, and the 2-chloromethyl-4-nitrophenyl P-L-glucopyranoside (102 7), in which the... 

A mixture of ethyl 2-chloromethyl-4-nitrophenyl hydrogen phosphate and 2 equivalents n-pentanol in 5 equivalents pyridine stored 2 days at room temp., then heated 6 hrs. at 90° ethyl n-pentyl hydrogen phosphate. Y 81%. F. e., also with phenols, s. T. Hata, Y. Mushika, and T, Mukaiyama, Tetrah. Let. 1970, 3505 Bull. Chem. Soc. Japan 44, 232 (1971) Chem. Pharm. Bull. 19, 687, 696 (1971). 

Chloro-6-deoxy-1,2- O -isopropylidene-a-D-glucofuranose, C-88 (2-Chloromethyl-4-nitrophenyl) a-D-glucopyranoside, C-120 (2-Chloromethyl-6-nitrophenyl) a-D-glucopyranoside, C-120 [2-(Chloromethyl)phenyl] glucopyranoside a-u-form, C-120 Crassinodin, C-155... 

Chloromethyl-4-nitrophenyl (N-carbobenzoxy)glycinate (137). This reagent resembles the /7-nitrophenyl derivative of carbobenzoxyglycine, which has been shown to be an excellent substrate for the proteolytic enzyme papain (436). Enzymic hydrolysis of (137) by papain releases the highly reactive HNB-Cl in situ, to provide selective alkylation of one or more tryptophyl residues present at the active site of papain 260). 

Mole, J. E., and H. R. Horton 2-Chloromethyl-4-nitrophenyl (N-Carbobenzoxy) glycinate. A New Reagent Designed to Introduce an Environmentally Sensitive Conformational Probe near the Active Site of Papain. Biochemistry 12, 5278-5285... 

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