α-2-nitrobenzyl 1'-cyano-5'-O-(4-monomethoxytrityl)-2'-deoxy-D-ribofuranoside

Base Information

Chemical Name:α-2-nitrobenzyl 1'-cyano-5'-O-(4-monomethoxytrityl)-2'-deoxy-D-ribofuranoside
CAS No.:357282-05-4
Molecular Formula:C₃₃H₃₀N₂O₇
Molecular Weight:566.61
Hs Code.:

Synonyms:α-2-nitrobenzyl 1'-cyano-5'-O-(4-monomethoxytrityl)-2'-deoxy-D-ribofuranoside

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Chemical Property of α-2-nitrobenzyl 1'-cyano-5'-O-(4-monomethoxytrityl)-2'-deoxy-D-ribofuranoside

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Technology Process of α-2-nitrobenzyl 1'-cyano-5'-O-(4-monomethoxytrityl)-2'-deoxy-D-ribofuranoside

There total 5 articles about α-2-nitrobenzyl 1'-cyano-5'-O-(4-monomethoxytrityl)-2'-deoxy-D-ribofuranoside 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: 35.0%

: 14470-28-1
mono-4-methoxytrityl chloride

: 357282-02-1
2-nitrobenzyl 1'-cyano-2'-deoxy-D-ribofuranoside

: 357282-05-4
α-2-nitrobenzyl 1'-cyano-5'-O-(4-monomethoxytrityl)-2'-deoxy-D-ribofuranoside

: 357282-03-2
β-2-nitrobenzyl 1'-cyano-5'-O-(4-monomethoxytrityl)-2'-deoxy-D-ribofuranoside

Guidance literature:: With dmap; In pyridine; at 24 ℃; for 18.5h;
DOI:10.1021/ol016255e

Reference yield:

: 3601-90-9
5-chloro-2-(((4-chlorobenzoyl)oxy)methyl)tetrahydrofuran-3-yl 4-chlorobenzoate

: 357282-05-4
α-2-nitrobenzyl 1'-cyano-5'-O-(4-monomethoxytrityl)-2'-deoxy-D-ribofuranoside

Guidance literature:: Multi-step reaction with 5 steps

1: 75 percent / tetrahydrofuran / 4 h / 4 - 20 °C

2: 82 percent / N-bromosuccinimide; benzoyl peroxide / CCl₄ / 2 h / 85 - 90 °C

3: 63 percent / silver triflate; 2,6-lutidine / CH₂Cl₂ / 4 h / 24 °C

4: 80 percent / methanolic ammonia / tetrahydrofuran / 3 h / 40 °C

5: 35 percent / 4-dimethylaminopyridine / pyridine / 18.5 h / 24 °C

With 2,6-dimethylpyridine; dmap; N-Bromosuccinimide; ammonia; silver trifluoromethanesulfonate; dibenzoyl peroxide; In tetrahydrofuran; pyridine; tetrachloromethane; dichloromethane;
DOI:10.1021/ol016255e

Reference yield:

: 357281-99-3
3,5-bis-O-(p-chlorobenzoyl)-2-deoxy-D-ribofuranosyl cyanide

: 357282-05-4
α-2-nitrobenzyl 1'-cyano-5'-O-(4-monomethoxytrityl)-2'-deoxy-D-ribofuranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 82 percent / N-bromosuccinimide; benzoyl peroxide / CCl₄ / 2 h / 85 - 90 °C

2: 63 percent / silver triflate; 2,6-lutidine / CH₂Cl₂ / 4 h / 24 °C

3: 80 percent / methanolic ammonia / tetrahydrofuran / 3 h / 40 °C

4: 35 percent / 4-dimethylaminopyridine / pyridine / 18.5 h / 24 °C

With 2,6-dimethylpyridine; dmap; N-Bromosuccinimide; ammonia; silver trifluoromethanesulfonate; dibenzoyl peroxide; In tetrahydrofuran; pyridine; tetrachloromethane; dichloromethane;
DOI:10.1021/ol016255e