+ Site Statistics
+ Search Articles
+ Subscribe to Site Feeds
EurekaMag Most Shared ContentMost Shared
EurekaMag PDF Full Text ContentPDF Full Text
+ PDF Full Text
Request PDF Full TextRequest PDF Full Text
+ Follow Us
Follow on FacebookFollow on Facebook
Follow on TwitterFollow on Twitter
Follow on Google+Follow on Google+
Follow on LinkedInFollow on LinkedIn

+ Translate

Direct synthesis of methyl phosphoramidates in carbohydrates

Organic & Biomolecular Chemistry 13(36): 9457-9461
Direct synthesis of methyl phosphoramidates in carbohydrates
A direct installation of a methyl phosphoramidate group by using methyl benzylphosphoramidochloridate into carbohydrates and amino acid is described. This one-step synthesis is efficient for both primary and secondary alcohols and exhibited excellent regioselectivity and functional group compatibility. Formation of a single diastereomer is observed in certain cases. The N-benzyl protecting group on methyl phosphoramidates is easily removed under mild conditions.

(PDF same-day service: $19.90)

Accession: 057630950

PMID: 26247390

DOI: 10.1039/c5ob01017a

Related references

Synthesis and evaluation against hepatitis C virus of 7-deaza analogues of 2'-C-methyl-6-O-methyl guanosine nucleoside and L-Alanine ester phosphoramidates. Bioorganic & Medicinal Chemistry Letters 23(7): 2260-2264, 2013

Synthesis of carbohydrate methyl phosphoramidates. Organic Letters 16(9): 2518-2521, 2014

Synthesis and phytotoxic properties of o o dimethyl phosphoramidates and o methyl phosphoric diamides. Indian Journal of Agricultural Sciences 56(10): 726-731, 1986

Synthesis of phosphoramidates: a facile approach based on the C-N bond formation via Ir-catalyzed direct C-H amidation. Organic Letters 16(20): 5466-5469, 2014

Steric and electrostatic interactions in reactions of carbohydrates. III. Direct displacement of the C-2 sulfonate of methyl 4,6-o-benzylidene-3-o-methyl-2-o-methylsulfonyl-beta-d-gluco-and-mannopyranosides. Journal of Organic Chemistry 39(22): 3223-3226, 1974

Septanose carbohydrates: synthesis and conformational studies of methyl alpha-D-glycero-D-idoseptanoside and methyl beta-D-glycero-D-guloseptanoside. Journal of Organic Chemistry 70(1): 24-38, 2004

Direct chemical synthesis of chiral methanol of 98% ee and its conversion to [(2)H1,(3)H]methyl tosylate and [(2)H1,(3)H-methyl]methionine. Journal of the American Chemical Society 127(40): 13934-13940, 2005

Direct organocatalytic de novo synthesis of carbohydrates. Angewandte Chemie 44(8): 1210-1212, 2005

Direct aerobic photo-oxidative synthesis of aromatic methyl esters from methyl aromatics via dimethyl acetals. Organic Letters 12(16): 3645-3647, 2010

Stereospecific synthesis of c methyl branched carbohydrates with tetramethylzirconium iv. Carbohydrate Research 207(1): 33-38, 1990