5'R-(p-methoxybenzyl)amino-5'-diethylphosphonyl-2',3'-di-O-tert-butyldimethylsilyl-N⁴-acetyl cytidine

Base Information

• Chemical Name: 5'R-(p-methoxybenzyl)amino-5'-diethylphosphonyl-2',3'-di-O-tert-butyldimethylsilyl-N⁴-acetyl cytidine
• CAS No.: 588718-65-4
• Molecular Formula: C₃₅H₆₁N₄O₉PSi₂
• Molecular Weight: 769.035

Synonyms:5'R-(p-methoxybenzyl)amino-5'-diethylphosphonyl-2',3'-di-O-tert-butyldimethylsilyl-N⁴-acetyl cytidine

Chemical Property of 5'R-(p-methoxybenzyl)amino-5'-diethylphosphonyl-2',3'-di-O-tert-butyldimethylsilyl-N⁴-acetyl cytidine

Chemical Property:

Purity/Quality:

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Technology Process of 5'R-(p-methoxybenzyl)amino-5'-diethylphosphonyl-2',3'-di-O-tert-butyldimethylsilyl-N⁴-acetyl cytidine

There total 3 articles about 5'R-(p-methoxybenzyl)amino-5'-diethylphosphonyl-2',3'-di-O-tert-butyldimethylsilyl-N⁴-acetyl cytidine 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:

1-(2',3'-di-O-tert-butyldimethylsilyl-β-D-ribo-penta-1',4'-furanosyl)-N4-acetylcytosine (487059-08-5) → 5'R-(p-methoxybenzyl)amino-5'-diethylphosphonyl-2',3'-di-O-tert-butyldimethylsilyl-N4-acetyl cytidine (588718-65-4)

Guidance literature:

Multi-step reaction with 3 steps

1: EDC; DMSO; pyr / TFA / benzene

2: benzene / 4 h / Heating

3: 55 mg / LHMDS / tetrahydrofuran / 24 h / 20 °C

With pyridine; dimethyl sulfoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; lithium hexamethyldisilazane; trifluoroacetic acid; In tetrahydrofuran; benzene; 1: Moffatt oxidation;

DOI:10.1021/jo030050x

Reference yield:

phosphonic acid diethyl ester (762-04-9) + N-[1-((2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-{[(E)-4-methoxy-benzylimino]-methyl}-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-acetamide (1054628-42-0) → 5'R-(p-methoxybenzyl)amino-5'-diethylphosphonyl-2',3'-di-O-tert-butyldimethylsilyl-N4-acetyl cytidine (588718-65-4) + 5'S-(p-methoxybenzyl)amino-5'-diethylphosphonyl-2',3'-di-O-tert-butyldimethylsilyl-N4-acetyl cytidine (588718-54-1)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at 20 ℃; for 24h;

DOI:10.1021/jo030050x

Reference yield:

N-{1-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-formyl-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-acetamide (487059-09-6) → 5'R-(p-methoxybenzyl)amino-5'-diethylphosphonyl-2',3'-di-O-tert-butyldimethylsilyl-N4-acetyl cytidine (588718-65-4)

Guidance literature:

Multi-step reaction with 2 steps

1: benzene / 4 h / Heating

2: 55 mg / LHMDS / tetrahydrofuran / 24 h / 20 °C

With lithium hexamethyldisilazane; In tetrahydrofuran; benzene;

DOI:10.1021/jo030050x

upstream raw materials:

phosphonic acid diethyl ester

N-[1-((2R,3R,4R,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-{[(E)-4-methoxy-benzylimino]-methyl}-tetrahydro-furan-2-yl)-2-oxo-1,2-dihydro-pyrimidin-4-yl]-acetamide

N-{1-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-formyl-tetrahydro-furan-2-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-acetamide

1-(2',3'-di-O-tert-butyldimethylsilyl-β-D-ribo-penta-1',4'-furanosyl)-N⁴-acetylcytosine

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