1-(4-Thio-beta-D-ribofuranosyl)cytosine

Base Information

• Chemical Name: 1-(4-Thio-beta-D-ribofuranosyl)cytosine
• CAS No.: 93080-09-2
• Molecular Formula: C₉H₁₃N₃O₄S
• Molecular Weight: 259.286
• Mol file: 93080-09-2.mol

Synonyms:4'-thio-cytidine;4'-Thio-β-D-ribofuranosylcytosin;1-(4-thio-β-D-ribofuranosyl)cytosine;4'-thiocytidine;1-<4-Thio-β-D-ribofuranosyl>-cytosin;4-Amino-1-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-thiophen-2-yl)-1H-pyrimidin-2-one;

Chemical Property of 1-(4-Thio-beta-D-ribofuranosyl)cytosine

Chemical Property:

• PSA: 146.90000
• LogP: -1.26520

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-(4-Thio-beta-D-ribofuranosyl)cytosine

There total 16 articles about 1-(4-Thio-beta-D-ribofuranosyl)cytosine 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: 72.0%

N4-benzoyl-1-(4-thio-β-D-ribo-pentofuranosyl)cytosine (159981-07-4) → 4'-thiocytidine (93080-09-2)

Guidance literature:

With methanol; ammonia; for 24h;

DOI:10.1080/15257779408013205

Reference yield: 56.0%

N-{1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-acetamide → 4'-thiocytidine (93080-09-2)

Guidance literature:

N-{1-[6-(tert-butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-tetrahydro-thieno[3,4-d][1,3]dioxol-4-yl]-2-oxo-1,2-dihydro-pyrimidin-4-yl}-acetamide; With ammonium hydroxide; In methanol; water;

With Dowex 50W H⁽¹⁺⁾; In methanol;

DOI:10.1016/j.tetlet.2005.11.049

Reference yield:

N4-acetyl-1-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine (291758-17-3) → 4'-thiocytidine (93080-09-2)

Guidance literature:

Multi-step reaction with 2 steps

1: ammonium fluoride / methanol / 12 h / Heating

2: NH₃ / methanol / 24 h / 20 °C

With ammonium fluoride; ammonia; In methanol; 1: Desilylation / 2: Amminolysis;

DOI:10.1021/ja000541o

upstream raw materials:

N⁴-benzoyl-1-(4-thio-β-D-ribo-pentofuranosyl)cytosine

1,4-anhydro-2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-sulfinyl-D-ribitol

N⁴-acetyl-1-[2-O-(2,4-dimethoxybenzoyl)-3,5-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-4-thio-β-D-ribofuranosyl]cytosine

methyl 2,3,5-tri-O-benzyl-D-ribofuranoside