(3'S,5'R)-N4-benzoyl-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)cytidine

Base Information

Chemical Name:(3'S,5'R)-N4-benzoyl-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)cytidine
CAS No.:1370411-73-6
Molecular Formula:C₃₄H₃₃N₃O₇
Molecular Weight:595.652
Hs Code.:

Synonyms:(3'S,5'R)-N4-benzoyl-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)cytidine

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Chemical Property of (3'S,5'R)-N4-benzoyl-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)cytidine

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Technology Process of (3'S,5'R)-N4-benzoyl-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)cytidine

There total 1 articles about (3'S,5'R)-N4-benzoyl-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)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: 98.0%

: 26661-13-2
4-N-benzoylcytosine

: 1370411-71-4
(2S,3R,3aR,6R,6aR)-3a,6-bis(benzyloxy)-2-(acetyloxy)-hexahydro-2H-cyclopenta[b]furan-3-yl acetate

: 1370411-73-6
(3'S,5'R)-N4-benzoyl-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)cytidine

Guidance literature:: 4-N-benzoylcytosine; (2S,3R,3aR,6R,6aR)-3a,6-bis(benzyloxy)-2-(acetyloxy)-hexahydro-2H-cyclopenta[b]furan-3-yl acetate; With N,O-bis-(trimethylsilyl)-acetamide; In acetonitrile; at 20 ℃; for 1h; Inert atmosphere;

With tin(IV) chloride; In acetonitrile; at 20 ℃; Inert atmosphere;
DOI:10.1021/jo300554w

Reference yield: 52.0%

: 1370411-73-6
(3'S,5'R)-N4-benzoyl-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)cytidine

: 1370411-75-8
(3'S,5'R)-N4-benzoyl-1-(2'-hydroxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)cytidine

Guidance literature:: (3'S,5'R)-N4-benzoyl-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)cytidine; With sodium hydroxide; In tetrahydrofuran; methanol; water; at 0 ℃; for 0.75h; Inert atmosphere;

With ammonium chloride; In tetrahydrofuran; methanol; water; at 20 ℃; for 0.166667h;
DOI:10.1021/jo300554w

Reference yield:

: 1370411-73-6
(3'S,5'R)-N4-benzoyl-1-(2'-acetoxy-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)cytidine

: 1370411-77-0
(3'S,5'R)-N4-benzoyl-1-(2'-O-tert-butydimethylsilyl-3',5'-O-dibenzyl-3',5'-ethano-β-D-ribofuranosyl)cytidine

Guidance literature:: Multi-step reaction with 2 steps

1.1: sodium hydroxide / tetrahydrofuran; methanol; water / 0.75 h / 0 °C / Inert atmosphere

1.2: 0.17 h / 20 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 24 h / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; sodium hydroxide; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide;
DOI:10.1021/jo300554w