1-[2-Deoxy-3,5-bis-O-(4-methylbenzoyl)-alpha-D-erythro-pentofuranosyl]-5-iodo-2,4(1H,3H)-pyrimidinedione

Base Information

• Chemical Name: 1-[2-Deoxy-3,5-bis-O-(4-methylbenzoyl)-alpha-D-erythro-pentofuranosyl]-5-iodo-2,4(1H,3H)-pyrimidinedione
• CAS No.: 104267-95-0
• Molecular Formula: C₂₅H₂₃IN₂O₇
• Molecular Weight: 590.371
• DSSTox Substance ID: DTXSID801113412
• Mol file: 104267-95-0.mol

Synonyms:DTXSID801113412;1-[2-Deoxy-3,5-bis-O-(4-methylbenzoyl)-alpha-D-erythro-pentofuranosyl]-5-iodo-2,4(1H,3H)-pyrimidinedione;104267-95-0

Chemical Property of 1-[2-Deoxy-3,5-bis-O-(4-methylbenzoyl)-alpha-D-erythro-pentofuranosyl]-5-iodo-2,4(1H,3H)-pyrimidinedione

Chemical Property:

• XLogP3: 3.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 8
• Exact Mass: 590.05500
• Heavy Atom Count: 35
• Complexity: 862

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC1=CC=C(C=C1)C(=O)OCC2C(CC(O2)N3C=C(C(=O)NC3=O)I)OC(=O)C4=CC=C(C=C4)C
• Isomeric SMILES: CC1=CC=C(C=C1)C(=O)OC[C@@H]2[C@H](C[C@H](O2)N3C=C(C(=O)NC3=O)I)OC(=O)C4=CC=C(C=C4)C

Technology Process of 1-[2-Deoxy-3,5-bis-O-(4-methylbenzoyl)-alpha-D-erythro-pentofuranosyl]-5-iodo-2,4(1H,3H)-pyrimidinedione

There total 5 articles about 1-[2-Deoxy-3,5-bis-O-(4-methylbenzoyl)-alpha-D-erythro-pentofuranosyl]-5-iodo-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: 52.0%

1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-5-iodouracil (31356-86-2) → 3',5'-di-O-(p-toluoyl)-5-iodo-α-2'-desoxyuridine (104267-95-0)

Guidance literature:

1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-5-iodouracil; With 1,1,1,3,3,3-hexamethyl-disilazane; In toluene; for 1h; Heating;

With trimethylsilyl trifluoromethanesulfonate; In acetonitrile; at 30 ℃; for 40h;

DOI:10.1016/j.bmcl.2006.11.052

Reference yield:

5-iodo-2,4-bis-O-trimethylsilyluracil (38953-72-9) + 2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride (4330-21-6) → 1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-5-iodouracil (31356-86-2) + 3',5'-di-O-(p-toluoyl)-5-iodo-α-2'-desoxyuridine (104267-95-0)

Guidance literature:

With pyridine; In dichloromethane; for 1h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Ambient temperature;

DOI:10.1021/jm00112a011

Reference yield:

5-Iodo-2'-deoxyuridine (54-42-2,162239-35-2) → 3',5'-di-O-(p-toluoyl)-5-iodo-α-2'-desoxyuridine (104267-95-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 86 percent / pyridine / 5 h / 20 °C

2.1: hexamethyldisilazane / toluene / 1 h / Heating

2.2: 52 percent / TMSOTf / acetonitrile / 40 h / 30 °C

With pyridine; 1,1,1,3,3,3-hexamethyl-disilazane; In toluene;

DOI:10.1016/j.bmcl.2006.11.052

upstream raw materials:

5-iodo-2,4-bis-O-trimethylsilyluracil

2-deoxy-3,5-di-O-p-toluoyl-α-D-erythro-pentofuranosyl chloride

1-[2-deoxy-3,5-di-O-(p-toluoyl)-β-D-erythro-pentofuranosyl]-5-iodouracil

5-Iodo-2'-deoxyuridine

Downstream raw materials:

5-furan-2-yl-1-(α-D-2-deoxyribofuranos-1-yl)uracil

N-{1-[(2S,4S,5R)-5-[Bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-2-oxo-5-prop-1-ynyl-1,2-dihydro-pyrimidin-4-yl}-benzamide

5'-O-(4,4'-dimethoxytrityl)-N-4-benzoyl-5-(propyn-1-yl)-α,2'-deoxycytidine

4-Amino-1-[(2S,4S,5R)-5-[bis-(4-methoxy-phenyl)-phenyl-methoxymethyl]-4-(tert-butyl-dimethyl-silanyloxy)-tetrahydro-furan-2-yl]-5-prop-1-ynyl-1H-pyrimidin-2-one

Refernces

• 1、 Morvan, Francois,Zeidler, Joanna,Rayner, Bernard. "α-Oligodeoxynucleotides containing 5-propynyl analogs of α-deoxyuridine and α-deoxycytidine: Synthesis and base pairing properties". . p. 71 - 82. Retrieved 2007/10/03.