1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-2,4(1H,3H)-pyrimidinedione

Base Information

• Chemical Name: 1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-2,4(1H,3H)-pyrimidinedione
• CAS No.: 200435-92-3
• Molecular Formula: C10H12 N2 O6
• Molecular Weight: 256.21200
• Mol file: 200435-92-3.mol

Synonyms:2,4(1H,3H)-Pyrimidinedione,1-[2,5-anhydro-4-C-(hydroxymethyl)-a-L-lyxofuranosyl]- (9CI);

Chemical Property of 1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-2,4(1H,3H)-pyrimidinedione

Chemical Property:

• Melting Point: 239-243 °C(Solv: methanol (67-56-1))
• PKA: 9.30±0.10(Predicted)
• PSA: 114.04000
• Density: 1.695
• LogP: -2.03150

Purity/Quality:

98%, ^*data from raw suppliers

2’-O,4’-C-Methyleneuridine 99.49% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2''-?O,?4''-?C-?Methyleneuridine is bridged nucleic acid which displays high binding affinities to DNA and RNA when paired with a phenoxazine base.

Technology Process of 1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-2,4(1H,3H)-pyrimidinedione

There total 39 articles about 1-[2,5-Anhydro-4-C-(hydroxymethyl)-alpha-L-lyxofuranosyl]-2,4(1H,3H)-pyrimidinedione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

1-((1S,3R,4R,7S)-7-(benzyloxy)-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)pyrimidine-2,4(1H,3H)-dione (200435-91-2) → 1-((1S,3R,4R,7S)-7-hydroxy-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)pyrimidine-2,4(1H,3H)-dione (200435-92-3)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃; for 15h;

DOI:10.1016/S0968-0896(00)00325-4

Reference yield: 100.0%

Benzoic acid (1R,3R,4R,7S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-hydroxy-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester (293751-31-2) → 1-((1S,3R,4R,7S)-7-hydroxy-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)pyrimidine-2,4(1H,3H)-dione (200435-92-3)

Guidance literature:

With methanol; sodium methylate; at 20 ℃; for 0.166667h;

DOI:10.1016/S0960-894X(00)00434-0

Reference yield: 84.6%

C26H30N2O6Si (1174917-62-4) → 1-((1S,3R,4R,7S)-7-hydroxy-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)pyrimidine-2,4(1H,3H)-dione (200435-92-3)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

upstream raw materials:

1-((1S,3R,4R,7S)-7-(benzyloxy)-1-(hydroxymethyl)-2,5-dioxabicyclo[2.2.1]heptan-3-yl)pyrimidine-2,4(1H,3H)-dione

(1S,3R,4R,7S)-7-benzyloxy-1-benzyloxymethyl-3-(uracil-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

Benzoic acid (1R,3R,4R,7S)-3-(2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-7-hydroxy-2,5-dioxa-bicyclo[2.2.1]hept-1-ylmethyl ester

2',3'-O-benzylidene-4'-(p-toluenesulfonyloxymethyl)uridine

Downstream raw materials:

(1S,3R,4R,7S)-7-hydroxy-1-hydroxymethyl-(thymin-1-yl)-2,5-dioxabicyclo[2.2.1]heptane

1-[(1R,4R,6R,7S)-4-[[bis(4-methoxyphenyl)phenylmethoxy]methyl]-7-hydroxy-2,5-dioxabicyclo[2.2.1]heptan-6-yl]-5-methylpyrimidine-2,4-dione

(1R,3R,4R,7S)-3-(thymine-1-yl)-1-(4,4′-dimethoxytrityloxy)-7-(2-cyanoethoxy(diisopropylamino)phosphinoxymethyl)-2,5-dioxabicyclo[2.2.1]heptane

5′-O-(4,4′-dimethoxytrityl)-2′-O,4′-C-methylenethymidine-3′-[O-(2-cyanoethyl)-(N,N-diisopropyl)]-phosphoramidite