3'-O-{N_α-(3,4-dimethoxy-6-nitrobenzyloxycarbonyl)-N_ε-[5-(dimethylamino)-1-naphthalenesulfonyl]-L-lysine-L-proline}-5'O-(tert-butyldiphenylsilyl)thymidine

Base Information

• Chemical Name: 3'-O-{N_α-(3,4-dimethoxy-6-nitrobenzyloxycarbonyl)-N_ε-[5-(dimethylamino)-1-naphthalenesulfonyl]-L-lysine-L-proline}-5'O-(tert-butyldiphenylsilyl)thymidine
• CAS No.: 192070-12-5
• Molecular Formula: C₅₉H₇₁N₇O₁₅SSi
• Molecular Weight: 1178.4
• Mol file: 192070-12-5.mol

Synonyms:3'-O-{N_α-(3,4-dimethoxy-6-nitrobenzyloxycarbonyl)-N_ε-[5-(dimethylamino)-1-naphthalenesulfonyl]-L-lysine-L-proline}-5'O-(tert-butyldiphenylsilyl)thymidine

Chemical Property of 3'-O-{N_α-(3,4-dimethoxy-6-nitrobenzyloxycarbonyl)-N_ε-[5-(dimethylamino)-1-naphthalenesulfonyl]-L-lysine-L-proline}-5'O-(tert-butyldiphenylsilyl)thymidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3'-O-{N_α-(3,4-dimethoxy-6-nitrobenzyloxycarbonyl)-N_ε-[5-(dimethylamino)-1-naphthalenesulfonyl]-L-lysine-L-proline}-5'O-(tert-butyldiphenylsilyl)thymidine

There total 8 articles about 3'-O-{N_α-(3,4-dimethoxy-6-nitrobenzyloxycarbonyl)-N_ε-[5-(dimethylamino)-1-naphthalenesulfonyl]-L-lysine-L-proline}-5'O-(tert-butyldiphenylsilyl)thymidine 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: 89.0%

(S)-Pyrrolidine-2-carboxylic acid (2R,3S,5R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester (192070-14-7) + (S)-2-(4,5-Dimethoxy-2-nitro-benzyloxycarbonylamino)-6-(5-dimethylamino-naphthalene-1-sulfonylamino)-hexanoic acid (192070-13-6) → 3'-O-{Nα-(3,4-dimethoxy-6-nitrobenzyloxycarbonyl)-Nε-[5-(dimethylamino)-1-naphthalenesulfonyl]-L-lysine-L-proline}-5'O-(tert-butyldiphenylsilyl)thymidine (192070-12-5)

Guidance literature:

With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 25 ℃; for 12h;

DOI:10.1021/jo9702608

Reference yield:

5-(dimethylamino)naphth-1-ylsulfonyl chloride (605-65-2) → 3'-O-{Nα-(3,4-dimethoxy-6-nitrobenzyloxycarbonyl)-Nε-[5-(dimethylamino)-1-naphthalenesulfonyl]-L-lysine-L-proline}-5'O-(tert-butyldiphenylsilyl)thymidine (192070-12-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / Et₃N / CH₂Cl₂ / 12 h / 25 °C

2: TFA / CH₂Cl₂ / 2 h / 25 °C

3: 52 percent / aq. NaHCO₃ / dioxane / 12 h / 25 °C

4: 89 percent / N-hydroxybenzotriazole, N-methylmorpholine, 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 12 h / 0 - 25 °C

With 4-methyl-morpholine; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid; In 1,4-dioxane; dichloromethane;

DOI:10.1021/jo9702608

Reference yield:

N(ε)-5-(dimethylamino)naphthalene-1-sulfonyl-L-lysine (1101-84-4) → 3'-O-{Nα-(3,4-dimethoxy-6-nitrobenzyloxycarbonyl)-Nε-[5-(dimethylamino)-1-naphthalenesulfonyl]-L-lysine-L-proline}-5'O-(tert-butyldiphenylsilyl)thymidine (192070-12-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 52 percent / aq. NaHCO₃ / dioxane / 12 h / 25 °C

2: 89 percent / N-hydroxybenzotriazole, N-methylmorpholine, 1-(3-(dimethylamino)propyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 12 h / 0 - 25 °C

With 4-methyl-morpholine; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In 1,4-dioxane; dichloromethane;

DOI:10.1021/jo9702608

upstream raw materials:

(S)-Pyrrolidine-2-carboxylic acid (2R,3S,5R)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-tetrahydro-furan-3-yl ester

(S)-2-(4,5-Dimethoxy-2-nitro-benzyloxycarbonylamino)-6-(5-dimethylamino-naphthalene-1-sulfonylamino)-hexanoic acid

5-(dimethylamino)naphth-1-ylsulfonyl chloride

N^(ε)-5-(dimethylamino)naphthalene-1-sulfonyl-L-lysine

Downstream raw materials:

5'-O-tert-butyldiphenylsilylthymidine