22976-90-5

Usage

InChI:InChI=1/C16H23N5O12/c17-6(8(24)4(22)3-32-15(18)30)12(27)20-7(14(28)29)11-9(25)10(26)13(33-11)21-2-1-5(23)19-16(21)31/h1-2,4,6-11,13,22,24-26H,3,17H2,(H2,18,30)(H,20,27)(H,28,29)(H,19,23,31)

Upstream product

• 205449-16-7 (S)-[(S)-2-tert-Butoxycarbonylamino-2-((4S,5S)-5-carbamoyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetylamino]-[(2R,3S,4R,5R)-5-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-3,4-dihydroxy-tetrahydro-furan-2-yl]-acetic acid 
• 205449-11-2 (S)-[(4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-trifluoromethanesulfonyloxy-acetic acid methyl ester 
• 205449-18-9 (R)-Acetoxy-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetic acid methyl ester 
• 205449-09-8 Acetoxy-[(4R,5S)-5-(tert-butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetic acid methyl ester 
• 205449-07-6 Methyl 5-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-L-lyxonate 
• 205449-10-1 Methyl 5-O-tert-butyldiphenylsilyl-3,4-O-isopropylidene-L-xylonate 
• 205449-13-4 Methyl 5-O-tert-butyldiphenylsilyl-2-(tert-butoxycarbonyl)amino-2-deoxy-3,4-O-isopropylidene-L-xylonate 
• 205449-12-3 Methyl 2-azido-5-O-tert-butyldiphenylsilyl-2-deoxy-3,4-O-isopropylidene-L-xylonate 
• 205449-15-6 Benzyl 5-O-(aminocarbonyl)-2-(tert-butoxycarbonyl)amino-2-deoxy-3,4-O-isopropylidene-L-xylonate 
• 172847-83-5 (S)-tert-Butoxycarbonylamino-((4S,5S)-5-carbamoyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-acetic acid 2,5-dioxo-pyrrolidin-1-yl ester 
• 205449-14-5 methyl 2-N-[(tert-butoxycarbonyl)amino]-2-deoxy-3,4-O-isopropylidene-L-xylonate 
• 90661-54-4 5-O-(aminocarbonyl)-2-[((1,1-dimethylethyl)oxycarbonyl)amino]-2-deoxy-3,4-O-(1-methylethylidene)-L-xylonic acid 
• 105309-43-1 methyl 5-O-(aminocarbonyl)-2-<(N-tert-butoxycarbonyl)amino>-2-deoxy-3,4-O-isopropylidene-L-xylonate 

Relevant academic research and scientific papers

Unified Total Synthesis of Polyoxins J, L, and Fluorinated Analogues on the Basis of Decarbonylative Radical Coupling Reactions

Polyoxins J (1 a) and L (1 b) are important nucleoside antibiotics. The complex and densely functionalized dipeptide structures of 1 a and 1 b contain thymine and uracil nucleobases, respectively. Herein we report the unified total synthesis of 1 a, 1 b, and their artificial analogues 1 c and 1 d with trifluorothymine and fluorouracil structures. Decarbonylative radical coupling between α-alkoxyacyl tellurides and a chiral glyoxylic oxime ether led to chemo- and stereoselective construction of the ribonucleoside α-amino acid structures of 1 a–d without damaging the preinstalled nucleobases. The high applicability of the radical-based methodology was further demonstrated by preparation of the trihydroxynorvaline moiety of 1 a–d. The two amino acid fragments were connected and elaborated into 1 a–d (longest linear sequence: 11 steps). Compounds 1 a and 1 b assembled in this way exhibited potent activity against true fungi, while only 1 d was active against Gram-positive bacteria.

A convenient synthesis of a N-protected l-carbamoylpolyoxamic acid derivative: Total synthesis of (+)-polyoxin J and (+)-polyoxin L1

A convenient synthesis of the N-protected L-carbamoylpolyoxamic acid derivative 7 from 4-O-tert-butyldiphenylsilyl-2,3-isopropylidene-L-threose (8) using vinylmagnesium bromide and its application to the total syntheses of the peptidyl nucleoside antibiotics, polyoxins J (1) and L (2), are described.

Total syntheses of (-)-polyoxin J and (-)-polyoxin L

A convenient synthesis of the N-protected L-carbamoylpolyoxamic acid derivative (7) from 4-O-tert-butyldiphcnylsilyl-2,3-isopropylidene-L-threose (8) using vinylmagnesium bromide and its application to the total syntheses of the peptidyl nucleoside antibiotics, polyoxins J (1) and L (2), are described.