1-<2'-C-cyano-2'-O-mesyl-3',5'-O-(tetraisopropyldisiloxan-1,3-diyl)-β-D-arabinofuranosyl>-4-N-(monomethoxytrityl)cytosine

Base Information

• Chemical Name: 1-<2'-C-cyano-2'-O-mesyl-3',5'-O-(tetraisopropyldisiloxan-1,3-diyl)-β-D-arabinofuranosyl>-4-N-(monomethoxytrityl)cytosine
• CAS No.: 160194-45-6
• Molecular Formula: C₄₃H₅₆N₄O₉SSi₂
• Molecular Weight: 861.176

Synonyms:1-<2'-C-cyano-2'-O-mesyl-3',5'-O-(tetraisopropyldisiloxan-1,3-diyl)-β-D-arabinofuranosyl>-4-N-(monomethoxytrityl)cytosine

Chemical Property of 1-<2'-C-cyano-2'-O-mesyl-3',5'-O-(tetraisopropyldisiloxan-1,3-diyl)-β-D-arabinofuranosyl>-4-N-(monomethoxytrityl)cytosine

Chemical Property:

Purity/Quality:

Safty Information:

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• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-<2'-C-cyano-2'-O-mesyl-3',5'-O-(tetraisopropyldisiloxan-1,3-diyl)-β-D-arabinofuranosyl>-4-N-(monomethoxytrityl)cytosine

There total 2 articles about 1-<2'-C-cyano-2'-O-mesyl-3',5'-O-(tetraisopropyldisiloxan-1,3-diyl)-β-D-arabinofuranosyl>-4-N-(monomethoxytrityl)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:

4-N-monomethoxytrityl-1-<3',5'-O-(tetraisopropyldisiloxan-1,3-diyl)-β-D-erythro-pentofuranos-2'-ulosyl>cytosine (141208-08-4) → 1-<2'-C-cyano-2'-O-mesyl-3',5'-O-(tetraisopropyldisiloxan-1,3-diyl)-β-D-arabinofuranosyl>-4-N-(monomethoxytrityl)cytosine (160194-45-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium bicarbonate / H₂O; diethyl ether / 72 h / Ambient temperature

2: pyridine / 72 h / 0 - 5 °C

With pyridine; sodium hydrogencarbonate; In diethyl ether; water;

DOI:10.1016/S0040-4020(01)85711-2

Reference yield:

methanesulfonyl chloride (124-63-0) + (2R,3aR,9aR)-3-Hydroxy-5,5,7,7-tetraisopropyl-2-(4-{[(4-methoxy-phenyl)-diphenyl-methyl]-amino}-2-oxo-2H-pyrimidin-1-yl)-tetrahydro-1,4,6,8-tetraoxa-5,7-disila-cyclopentacyclooctene-3-carbonitrile → 1-<2'-C-cyano-2'-O-mesyl-3',5'-O-(tetraisopropyldisiloxan-1,3-diyl)-β-D-ribofuranosyl>-4-N-(monomethoxytrityl)cytosine (160194-46-7) + 1-<2'-C-cyano-2'-O-mesyl-3',5'-O-(tetraisopropyldisiloxan-1,3-diyl)-β-D-arabinofuranosyl>-4-N-(monomethoxytrityl)cytosine (160194-45-6)

Guidance literature:

With pyridine; at 0 - 5 ℃; for 72h; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4020(01)85711-2

Reference yield: 67.0%

1-<2'-C-cyano-2'-O-mesyl-3',5'-O-(tetraisopropyldisiloxan-1,3-diyl)-β-D-arabinofuranosyl>-4-N-(monomethoxytrityl)cytosine (160194-45-6) → <1-<3',5'-O-(tetraisopropyldisiloxan-1,3-diyl)-β-D-arabinofuranosyl>-4-N-(monomethoxytrityl)cytosine>-2'-spiro-5''-(4''-amino-1'',2''-oxathiole-2'',2''-dioxide)

Guidance literature:

With caesium carbonate; In acetonitrile; for 24h; Ambient temperature;

DOI:10.1016/S0040-4020(01)85711-2

upstream raw materials:

methanesulfonyl chloride

4-N-monomethoxytrityl-1-<3',5'-O-(tetraisopropyldisiloxan-1,3-diyl)-β-D-erythro-pentofuranos-2'-ulosyl>cytosine

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