21027-33-8

Usage

InChI:InChI=1/C11H15N3O8/c12-4(10(19)20)7-5(16)6(17)9(22-7)14-1-3(2-15)8(18)13-11(14)21/h1,4-7,9,15-17H,2,12H2,(H,19,20)(H,13,18,21)/t4-,5-,6+,7+,9+/m0/s1

Upstream product

• 4433-40-3 5-(hydroxymethyl)pyrimidine-2,4-diol 
• 611184-75-9 Methyl 2,3-O-Isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside 
• 127646-32-6 (S)-((3aR,4S,6S,6aR)-6-Methoxy-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-trifluoromethanesulfonyloxy-thioacetic acid S-phenyl ester 
• 127646-33-7 Methyl -β-D-allofuranosid>uronate 
• 127646-30-4 Methyl 5,6-Dideoxy-2,3-O-isopropylidene-6-nitro-6-(phenylthio)-β-D-ribo-hex-5(Z)-enofuranoside 
• 127646-31-5 Phenyl (Methyl 2,3-O-isopropylidene-δ-D-allofuranosid)thiouronate 
• 58934-69-3 (S)-Azido-((2R,3S,4R)-3,4-dihydroxy-5-methoxy-tetrahydro-furan-2-yl)-acetic acid methyl ester 
• 32445-75-3 D-Ribose 
• 58763-00-1 ((3aR,4R,6S,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 310904-41-7 5-hydroxymethyl-1-(methyl 2',3'-di-O-acetyl-5'-carbobenzyloxyamino-5'-deoxy-β-D-allofuranosyluronate)uracil 
• 31517-04-1 5-trimethylsiloxymethyl-2,4-bis(trimethylsiloxy)pyrimidine 
• 155154-68-0 methyl (5-azido-5-deoxy-1,2,3-tri-O-acetyl-D-allofuranosid)uronate 
• 4433-40-3 5-hydroxymethyl uracil 
• 127646-37-1 5-hydroxymethyl-1-(methyl 2',3'-di-O-acetyl-5'-azido-5'-deoxy-β-D-allofuranosyluronate)uracil 

Downstream Products

• 19396-06-6 5-((2-amino-5-O-(carbamoyl)-2-deoxy-L-xylon)amido)-1,5-dideoxy-1-(3,4-dihydro-5-(hydroxymethyl)-2,4-dioxo-1(2H)-pyrimidinyl)-β-D-allofuranuronic acid 

Relevant academic research and scientific papers

First total syntheses of (+)-polyoxin B and (+)-Polyoxin D

First total syntheses of the peptidyl nucleoside antibiotics, polyoxins B (1) and D (2), are achieved based on the coupling reactions of the N-protected L-carbamoyl-polyoxamic acid derivative (6) with polyoxin C (8), 6 with polyoxin C acid (9), respectively.

(Phenylthio)nitromethane in the Total Synthesis of Polyoxin C

The stereospecific total synthesis of polyoxin C and the nucleoside analogue, uracil polyoxin C, is described.Condensation of (phenylthio)nitromethane with methyl 2,3-O-isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside 5 gave the (Z)-nitro olefin 6.Addition of potassium trimethylsilanoate and ozonolysis gave the α-hydroxy thioester 7, which was formed with excellent diastereoselectivity.The alcohol 7 was converted into polyoxin C (1) and uracil polyoxin C (2) via the azide 11 and base incorporation using the Vorbrueggen method.