(3S,5R)-3-[N⁶-(benzyloxycarbonyl)adenin-9-yl]-5-tert-butoxycarbonylaminomethyl-N-methoxycarbonylmethyl-2-pyrrolidinone

Base Information

• Chemical Name: (3S,5R)-3-[N⁶-(benzyloxycarbonyl)adenin-9-yl]-5-tert-butoxycarbonylaminomethyl-N-methoxycarbonylmethyl-2-pyrrolidinone
• CAS No.: 329005-80-3
• Molecular Formula: C₂₆H₃₁N₇O₇
• Molecular Weight: 553.575

Synonyms:(3S,5R)-3-[N⁶-(benzyloxycarbonyl)adenin-9-yl]-5-tert-butoxycarbonylaminomethyl-N-methoxycarbonylmethyl-2-pyrrolidinone

Chemical Property of (3S,5R)-3-[N⁶-(benzyloxycarbonyl)adenin-9-yl]-5-tert-butoxycarbonylaminomethyl-N-methoxycarbonylmethyl-2-pyrrolidinone

Chemical Property:

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Technology Process of (3S,5R)-3-[N⁶-(benzyloxycarbonyl)adenin-9-yl]-5-tert-butoxycarbonylaminomethyl-N-methoxycarbonylmethyl-2-pyrrolidinone

There total 13 articles about (3S,5R)-3-[N⁶-(benzyloxycarbonyl)adenin-9-yl]-5-tert-butoxycarbonylaminomethyl-N-methoxycarbonylmethyl-2-pyrrolidinone 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: 70.0%

[(3S,5R)-3-(6-Amino-purin-9-yl)-5-(tert-butoxycarbonylamino-methyl)-2-oxo-pyrrolidin-1-yl]-acetic acid methyl ester (329005-79-0) + N-benzyloxycarbonyl-N'-methylimidazolium triflate → (3S,5R)-3-[N6-(benzyloxycarbonyl)adenin-9-yl]-5-tert-butoxycarbonylaminomethyl-N-methoxycarbonylmethyl-2-pyrrolidinone (329005-80-3)

Guidance literature:

In dichloromethane;

DOI:10.1021/jo001000k

Reference yield:

(3S,5R)-3-benzyloxymethoxy-5-hydroxymethyl-N-[methoxycarbonylmethyl]-2-pyrrolidinone (329005-69-8) → (3S,5R)-3-[N6-(benzyloxycarbonyl)adenin-9-yl]-5-tert-butoxycarbonylaminomethyl-N-methoxycarbonylmethyl-2-pyrrolidinone (329005-80-3)

Guidance literature:

Multi-step reaction with 8 steps

1: 86 percent / Et₃N / CH₂Cl₂ / 2.25 h / 0 °C

2: 98 percent / NaN₃ / dimethylformamide / 80 °C

3: 89 percent / H₂ / 10percent Pd/C / ethyl acetate / 1.5 h / 20 °C / 760.05 Torr

4: 94 percent / H₂ / 10percent Pd(OH)2/C / methanol / 20 °C / 760.05 Torr

5: 99 percent / PPh₃; DEAD / dioxane / 0 - 20 °C

6: 88 percent / NaOMe / methanol / 0.5 h / 0 °C

7: 70 percent / PPh₃; DEAD / dioxane / 20 °C

8: 70 percent / CH₂Cl₂

With sodium azide; hydrogen; sodium methylate; triethylamine; triphenylphosphine; diethylazodicarboxylate; 10percent Pd/C; 10percent Pd(OH)2/C; In 1,4-dioxane; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 5: Mitsunobu reaction;

DOI:10.1021/jo001000k

Reference yield:

(3S,5R)-5-azidomethyl-3-benzyloxymethoxy-N-methoxycarbonylmethyl-2-pyrrolidinone (329005-71-2) → (3S,5R)-3-[N6-(benzyloxycarbonyl)adenin-9-yl]-5-tert-butoxycarbonylaminomethyl-N-methoxycarbonylmethyl-2-pyrrolidinone (329005-80-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 89 percent / H₂ / 10percent Pd/C / ethyl acetate / 1.5 h / 20 °C / 760.05 Torr

2: 94 percent / H₂ / 10percent Pd(OH)2/C / methanol / 20 °C / 760.05 Torr

3: 99 percent / PPh₃; DEAD / dioxane / 0 - 20 °C

4: 88 percent / NaOMe / methanol / 0.5 h / 0 °C

5: 70 percent / PPh₃; DEAD / dioxane / 20 °C

6: 70 percent / CH₂Cl₂

With hydrogen; sodium methylate; triphenylphosphine; diethylazodicarboxylate; 10percent Pd/C; 10percent Pd(OH)2/C; In 1,4-dioxane; methanol; dichloromethane; ethyl acetate; 3: Mitsunobu reaction;

DOI:10.1021/jo001000k

upstream raw materials:

[(3S,5R)-3-(6-Amino-purin-9-yl)-5-(tert-butoxycarbonylamino-methyl)-2-oxo-pyrrolidin-1-yl]-acetic acid methyl ester

adenine

(3R,5R)-5-tert-butoxycarbonylaminomethyl-3-hydroxy-N-methoxycarbonylmethyl-2-pyrrolidinone

(3S,5R)-5-tert-butoxycarbonylaminomethyl-3-hydroxy-N-methoxycarbonylmethyl-2-pyrrolidinone

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