127646-30-4

Upstream product

• 60595-16-6 (phenylthio)nitromethane 
• 611184-75-9 Methyl 2,3-O-Isopropylidene-β-D-ribo-pentodialdo-1,4-furanoside 
• 58763-00-1 ((3aR,4R,6S,6aR)-6-methoxy-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol 
• 32445-75-3 D-Ribose 

Downstream Products

• 127646-31-5 Phenyl (Methyl 2,3-O-isopropylidene-δ-D-allofuranosid)thiouronate 
• 24695-48-5 1-(5'-amino-5'-deoxy-α-D-allofuranuronosyl)uracil 
• 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 
• 21027-33-8 1-(5'-amino-5'-deoxy-β-D-allofuranosyluronic acid)-5-hydroxymethyluracil 
• 137232-76-9 phenyl (methyl 2,3-O-isopropylidene-5-succinimido-5-deoxy-β-D-allofuranoside)thiouronate 
• 137232-71-4 phenyl (methyl 2,3-O-isopropylidene-5-O-methyl-β-D-allofuranoside)thiouronate 
• 137232-70-3 phenyl (methyl 2,3-O-isopropylidene-5-O-methyl-β-D-allofuranoside)t 
• 137232-73-6 phenyl (methyl 2,3-O-isopropylidene-5-O-(phenylmethyl)-β-D-allofuranoside)thiouronate 
• 137232-72-5 phenyl (methyl 2,3-O-isopropylidene-5-O-(phenylmethyl)-β-D-allofuranoside)thiouronate 
• 137232-69-0 phenyl (methyl 2,3-O-isopropylidene-5-phthalimido-5-deoxy-β-D-allofuranoside thiouronate) 
• 137232-68-9 phenyl (methyl 2,3-O-isopropylidene-5-phthalimido-5-deoxy-β-D-allofuranoside)thiouronate 
• 137232-75-8 phenyl <(S)-methyl 2,3-O-isopropylidene-5-(toluene-4-sulfonamido)-5-deoxy-β-D-allofuranoside>thiouronate 
• 137232-78-1 methyl (methyl 2,3-O-isopropylidene-5-O-(phenylmethyl)-β-D-allofuranosid)uronate 
• 137232-79-2 methyl (methyl 2,3-O-isopropylidene-5-(toluene-4-sulfonamido)-5-deoxy-β-D-allofuranosid)uronate 

Relevant academic research and scientific papers

(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.