1-[(1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl]-5-methyl-pyrimidine-2,4-dione

Base Information

• Chemical Name: 1-[(1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl]-5-methyl-pyrimidine-2,4-dione
• CAS No.: 61849-27-2
• Molecular Formula: C11H16 N2 O4
• Molecular Weight: 240.259
• NSC Number: 163465
• Nikkaji Number: J776.542H
• ChEMBL ID: CHEMBL27473
• Mol file: 61849-27-2.mol

Synonyms:CHEMBL27473;Carba-dT;1-[(1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl]-5-methyl-pyrimidine-2,4-dione;Carba-T;D-Carbara-T;SCHEMBL22382008;BDBM50481091;NSC163465;NSC-163465;61849-27-2;Thymine,1-[3-hydroxy-4-(hydroxymethyl)cyclopentyl]-, trans,cis-(+/-)-;(+)-1-((1R,3S,4R)-3-Hydroxy-4-hydroxymethyl-cyclopentyl)-5-methyl-1H-pyrimidine-2,4-dione;2,3H)-Pyrimidinedione, 1-[3-hydroxy-4-(hydroxymethyl)cyclopentyl]-5-methyl-, (1.alpha.,3.beta.,4.alpha.)-(+-)-

Chemical Property of 1-[(1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl]-5-methyl-pyrimidine-2,4-dione

Chemical Property:

• Density: 1.367g/cm³
• XLogP3: -0.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 240.11100700
• Heavy Atom Count: 17
• Complexity: 380

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CC(C(C2)O)CO
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@@H]2C[C@@H]([C@H](C2)O)CO

Technology Process of 1-[(1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl]-5-methyl-pyrimidine-2,4-dione

There total 23 articles about 1-[(1R,3S,4R)-3-hydroxy-4-(hydroxymethyl)cyclopentyl]-5-methyl-pyrimidine-2,4-dione 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: 94.0%

8c-acetoxy-3-methyl-7,8,9,10-tetrahydro-6H-6r,9c-methano-pyrimido[2,1-b][1,3]oxazocin-2-one (87491-47-2) → (+/-)-1-<(1α,3β,4α)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-methyl-2,4-(1H,3H)pyrimidinedione (61849-27-2)

Guidance literature:

With sodium hydroxide; for 2h; Heating;

DOI:10.1002/jhet.5570200329

Reference yield: 88.0%

(+/-)-1-{4-[(benzyloxy)methyl]cyclopent-3-ol-1-yl}-3-[(benzyloxy)methyl]thymine → (+/-)-1-<(1α,3β,4α)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-methyl-2,4-(1H,3H)pyrimidinedione (61849-27-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; at 20 ℃; for 5h;

DOI:10.1135/cccc20061011

Reference yield: 83.0%

1-((1S,3R,4S)-3-Hydroxy-4-hydroxymethyl-cyclopentyl)-3-((E)-3-methoxy-2-methyl-acryloyl)-urea → (+/-)-1-<(1α,3β,4α)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-methyl-2,4-(1H,3H)pyrimidinedione (61849-27-2)

Guidance literature:

With ammonia; Heating;

DOI:10.1016/S0040-4039(99)01113-2

upstream raw materials:

8c-acetoxy-3-methyl-7,8,9,10-tetrahydro-6H-6r,9c-methano-pyrimido[2,1-b][1,3]oxazocin-2-one

(+/-)-1-{4-[(benzyloxy)methyl]cyclopent-3-en-1-yl}-3-[(benzyloxy)methyl]thymine

(+/-)-3-[(benzyloxy)methyl]cyclopent-3-en-1-ol

cyclopenta-1,3-diene

Downstream raw materials:

C-5'-O-trityl-2,3'-anhydrothymidine

(+/-)-1-<(1α,3β,4α)-3-(acetyloxy)-4-<(triphenylmethoxy)methyl>cyclopentyl>-5-methyl-2,4(1H,3H)-pyrimidinedione

(+/-)-5-methyl-1-<(1α,3β,4α)-3-(methanesulfonyloxy)-4-<(triphenylmethoxy)methyl>cyclopentyl>-2,4(1H,3H)-pyrimidinedione

(+/-)-1-<(1α,3α,4α)-3-hydroxy-4-(hydroxymethyl)cyclopentyl>-5-methyl-2,4(1H,3H)-pyrimidinedione