1-((2R,6S)-6-(hydroxymethyl)-4-tritylmorpholin-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

Base Information

• Chemical Name: 1-((2R,6S)-6-(hydroxymethyl)-4-tritylmorpholin-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione
• CAS No.: 914361-76-5
• Molecular Formula: C29H29N3O4
• Molecular Weight: 483.567
• European Community (EC) Number: 854-917-3
• Mol file: 914361-76-5.mol

Synonyms:914361-76-5;1-((2R,6S)-6-(hydroxymethyl)-4-tritylmorpholin-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione;1-[(2R,6S)-6-(hydroxymethyl)-4-tritylmorpholin-2-yl]-5-methylpyrimidine-2,4-dione;7 inverted exclamation mark -OH-N-trityl morpholinothymine;1-(6-Hydroxymethyl-4-trityl-morpholin-2-yl)-5-methyl-1H-pyrimidine-2,4-dione;7'-OH-N-trityl Morpholino thyMine;PMO Thymidine Precusor;SCHEMBL441127;SINOYLIIFJJPCM-IZZNHLLZSA-N;EX-A5903;ZB1833;HY-W357202;CS-0468398;F12895;A857337

Chemical Property of 1-((2R,6S)-6-(hydroxymethyl)-4-tritylmorpholin-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

Chemical Property:

• PSA: 87.56000
• LogP: 2.96670
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 483.21580641
• Heavy Atom Count: 36
• Complexity: 766

Purity/Quality:

99%, ^*data from raw suppliers

7'-Hydroxy-N-tritylmorpholino thymine monomer ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CN(C(=O)NC1=O)C2CN(CC(O2)CO)C(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5
• Isomeric SMILES: CC1=CN(C(=O)NC1=O)[C@H]2CN(C[C@H](O2)CO)C(C3=CC=CC=C3)(C4=CC=CC=C4)C5=CC=CC=C5

Technology Process of 1-((2R,6S)-6-(hydroxymethyl)-4-tritylmorpholin-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione

There total 8 articles about 1-((2R,6S)-6-(hydroxymethyl)-4-tritylmorpholin-2-yl)-5-methylpyrimidine-2,4(1H,3H)-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: 97.0%

7-O-(tert-butyldiphenylsilyl)-N-trityl morpholinothymidine (1415645-54-3) → 1-((2R,6S)-6-(hydroxymethyl)-4-tritylmorpholin-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (914361-76-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 1.5h;

Reference yield:

C10H15N3O4 (179073-10-0) + trityl chloride (76-83-5) → 1-((2R,6S)-6-(hydroxymethyl)-4-tritylmorpholin-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (914361-76-5)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide; for 1h; pH=8.5 - 9;

DOI:10.3762/bjoc.10.115

Reference yield:

5-Methyluridine (1463-10-1,642082-80-2) → 1-((2R,6S)-6-(hydroxymethyl)-4-tritylmorpholin-2-yl)-5-methylpyrimidine-2,4(1H,3H)-dione (914361-76-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / Molecular sieve; Inert atmosphere

2.1: sodium periodate; ammonium biborate tetrahydrate / methanol / 1.5 h / 20 °C / Molecular sieve; Inert atmosphere

2.2: 2 h / Molecular sieve; Inert atmosphere

3.1: triethylamine / N,N-dimethyl-formamide / 1 h / 0 °C / Molecular sieve; Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1.5 h / 20 °C

With 1H-imidazole; sodium periodate; ammonium biborate tetrahydrate; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1080/15257770.2012.724491

upstream raw materials:

5′-O-tert-butyldiphenylsilyl-O²-2′-anhydro-5-methyluridine

5-Methyluridine

7-O-(tert-butyldiphenylsilyl)-N-trityl morpholinothymidine

7-O-(tert-butyldiphenylsilyl)morpholinothymidine

Downstream raw materials:

C₃₅H₃₆ClF₃N₅O₆P

((2S,6R)-6-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-tritylmorpholin-2-yl)methyl (4-(pyrrolidin-1-yl)piperidin-1-yl)phosphonochloridate hydrochloride

isobutyl 3-(tert-butyldisulfanyl)-1-(1-(chloro(((2S,6R)-6-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-tritylmorpholin-2-yl)methoxy)phosphoryl)piperidin-4-ylamino)-1-oxopropan-2-ylcarbamate

((2S,6R)-6-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-tritylmorpholin-2-yl)methyl hexyl(methyl)phosphoramidochloridate

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