tert-butyl 2-(((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)carbamoyl)-2-(hydroxymethyl)-5-methylpyrrolidine-1-carboxylate

Base Information

Chemical Name:tert-butyl 2-(((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)carbamoyl)-2-(hydroxymethyl)-5-methylpyrrolidine-1-carboxylate
CAS No.:1621435-45-7
Molecular Formula:C₃₀H₄₀N₂O₇
Molecular Weight:540.657
Hs Code.:

Synonyms:tert-butyl 2-(((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)carbamoyl)-2-(hydroxymethyl)-5-methylpyrrolidine-1-carboxylate

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Chemical Property of tert-butyl 2-(((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)carbamoyl)-2-(hydroxymethyl)-5-methylpyrrolidine-1-carboxylate

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Technology Process of tert-butyl 2-(((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)carbamoyl)-2-(hydroxymethyl)-5-methylpyrrolidine-1-carboxylate

There total 12 articles about tert-butyl 2-(((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)carbamoyl)-2-(hydroxymethyl)-5-methylpyrrolidine-1-carboxylate 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: 32.5%

: 67580-86-3
(2S,3R)-benzyl 2-amino-3-(benzyloxy)butanoate hydrochloride

: 1621435-44-6
1-(tert-butoxycarbonyl)-2-(hydroxymethyl)-5-methylpyrrolidine-2-carboxylic acid

: 1621435-45-7
tert-butyl 2-(((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)carbamoyl)-2-(hydroxymethyl)-5-methylpyrrolidine-1-carboxylate

Guidance literature:: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 16h;

Reference yield:

: 54276-70-9
N‐(tert‐butoxycarbonyl)‐O‐benzyl‐L‐threonine benzyl ester

: 1621435-45-7
tert-butyl 2-(((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)carbamoyl)-2-(hydroxymethyl)-5-methylpyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: hydrogenchloride / methanol / 12 h / Inert atmosphere

2: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 0 - 20 °C

With hydrogenchloride; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In methanol; dichloromethane;

Reference yield:

: 149-87-1
Pyroglutamic acid

: 1621435-45-7
tert-butyl 2-(((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)carbamoyl)-2-(hydroxymethyl)-5-methylpyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 10 steps

1.1: thionyl chloride / 16 h / 0 - 20 °C

2.1: triethylamine; dmap / dichloromethane / 16 h / 0 - 20 °C

3.1: tetrahydrofuran; diethyl ether / 2 h / 0 °C / Inert atmosphere

4.1: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C

5.1: hydrogen; palladium 10% on activated carbon / ethanol / 16 h

6.1: triethylamine; dmap / dichloromethane / 16 h / 0 - 20 °C

7.1: lithium hexamethyldisilazane / tetrahydrofuran / 2 h / -78 °C

7.2: 2 h / -30 °C

8.1: sodium hydroxide / water; methanol; tetrahydrofuran / 8 h / 65 °C

9.1: hydrogen; palladium 10% on activated carbon / methanol / 16 h / 20 °C

10.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 16 h / 0 - 20 °C

With dmap; thionyl chloride; palladium 10% on activated carbon; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; water;