186839-90-7

Upstream product

• 3587-60-8 Benzyloxymethyl chloride 
• 58-96-8 uridine 

Downstream Products

• 581060-77-7 3-Benzyloxymethyl-1-((2R,3R,3aS,9aR)-3-hydroxy-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-2-yl)-1H-pyrimidine-2,4-dione 
• 581060-78-8 [(2R,3R,3aR,9aR)-2-(3-Benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-acetic acid methyl ester 
• 581060-80-2 carbonic acid 2-[5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-2-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-hydroxy-tetrahydro-furan-3-yloxy]-ethyl ester 9H-fluoren-9-ylmethyl ester 
• 581060-79-9 Carbonic acid 2-[(2R,3R,3aR,9aR)-2-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-5,5,7,7-tetraisopropyl-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacycloocten-3-yloxy]-ethyl ester 9H-fluoren-9-ylmethyl ester 
• 191479-26-2 3-((benzyloxy)methyl)-1-((3aR,4R,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl)pyrimidine-2,4(1H,3H)-dione 
• 1158951-41-7 3-[(benzyloxy)methyl]-1-(5-triphenylmethyl-β-D-ribofuranosyl)uracil 
• 186839-95-2 Bromo-acetic acid (2R,4S,5R)-5-(3-benzyloxymethyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-4-(tert-butyl-dimethyl-silanyloxy)-3-oxo-tetrahydro-furan-2-ylmethyl ester 
• 186839-92-9 3-Benzyloxymethyl-1-[(2R,3S,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-oxo-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 
• 186839-97-4 3-Benzyloxymethyl-1-[(2R,3R,3aR,7aR)-3-(tert-butyl-dimethyl-silanyloxy)-3a-hydroxy-5-oxo-hexahydro-furo[2,3-c]pyran-2-yl]-1H-pyrimidine-2,4-dione 
• 186839-93-0 3-Benzyloxymethyl-1-[(2R,3S,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-hydroxymethyl-4-oxo-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 
• 186839-91-8 3-Benzyloxymethyl-1-[(2R,3R,4R,5R)-3-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-4-hydroxy-tetrahydro-furan-2-yl]-1H-pyrimidine-2,4-dione 
• 1205122-20-8 C₃₁H₂₈Cl₄N₂O₈ 

Relevant academic research and scientific papers

DPAGT1 Inhibitors of Capuramycin Analogues and Their Antimigratory Activities of Solid Tumors

Capuramycin displays a narrow spectrum of antibacterial activity by targeting bacterial translocase I (MraY). In our program of development of new N-acetylglucosaminephosphotransferase1 (DPAGT1) inhibitors, we have identified that a capuramycin phenoxypiperidinylbenzylamide analogue (CPPB) inhibits DPAGT1 enzyme with an IC50 value of 200 nM. Despite a strong DPAGT1 inhibitory activity, CPPB does not show cytotoxicity against normal cells and a series of cancer cell lines. However, CPPB inhibits migrations of several solid cancers including pancreatic cancers that require high DPAGT1 expression in order for tumor progression. DPAGT1 inhibition by CPPB leads to a reduced expression level of Snail but does not reduce E-cadherin expression level at the IC50 (DPAGT1) concentration. CPPB displays a strong synergistic effect with paclitaxel against growth-inhibitory action of a patient-derived pancreatic adenocarcinoma, PD002: paclitaxel (IC50: 1.25 μM) inhibits growth of PD002 at 0.0024-0.16 μM in combination with 0.10-2.0 μM CPPB (IC50: 35 μM).

Concise synthesis of capuramycin

A concise total synthesis of capuramycin (1), a promising preclinical TB drug lead, is achieved by high-yield formations of the cyanohydrin 5a and 4″,5″-glycal derivative 12. Capuramycin can be synthesized in eight steps from the uridine building block 5a with 30% overall yield. The synthetic intermediates reported here are useful for generation of analogs to improve pharmacokinetic properties of capuramycin.

Nucleosides and Nucleotides. 163. Synthesis of 3′-β-Branched Uridine Derivatives via Intramolecular Reformatsky-Type Reaction Promoted by Samarium Diiodide

A novel efficient method for the synthesis of 3′-β-branched uridines starting from uridine was developed, in which a SmI2-promoted intramolecular Reformatsky-type reaction was effectively used. 5′-O-(Bromoacetyl)-3′-ketouridine derivatives 12, 26, and 27 were synthesized from uridine and were subjected to an intramolecular Reformatsky-type reaction. When 12, 26, and 27 were treated with 2.0 equiv of SmI2 in THF at -78°C, intramolecular carbon-carbon bond formation at the 3′-β-position proceeded smoothly to give the corresponding 3′,5′-lactones 14, 28, and 29 in high yields, respectively. Treatment of 28 with NH3/MeOH gave the 3′-β-branched uridine derivative 32 quantitatively, which was then deprotected to give 3′-C-(carbamoylmethyl)uridine (33).