tert-butyl (S)-2-((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)-1-oxo-2,5-diazaspiro[3.4]octane-5-carboxylate

Base Information

• Chemical Name: tert-butyl (S)-2-((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)-1-oxo-2,5-diazaspiro[3.4]octane-5-carboxylate
• CAS No.: 1621435-14-0
• Molecular Formula: C₂₉H₃₆N₂O₆
• Molecular Weight: 508.615
• Mol file: 1621435-14-0.mol

Synonyms:tert-butyl (S)-2-((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)-1-oxo-2,5-diazaspiro[3.4]octane-5-carboxylate

Chemical Property of tert-butyl (S)-2-((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)-1-oxo-2,5-diazaspiro[3.4]octane-5-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (S)-2-((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)-1-oxo-2,5-diazaspiro[3.4]octane-5-carboxylate

There total 21 articles about tert-butyl (S)-2-((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)-1-oxo-2,5-diazaspiro[3.4]octane-5-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:

tert-butyl (S)-2-(((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)carbamoyl)-2-(hydroxymethyl)pyrrolidine-1-carboxylate → tert-butyl (S)-2-((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)-1-oxo-2,5-diazaspiro[3.4]octane-5-carboxylate (1621435-14-0)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 15 - 20 ℃; for 4h; Inert atmosphere;

Reference yield:

tert-butyl 2-(((2S, 3R)-1, 3-bis (benzyloxy)-1-oxobutan-2-yl) carbamoyl)-2-(hydroxymethyl) pyrrolidine-1-carboxylate (1621435-13-9) → tert-butyl (R)-2-((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)-1-oxo-2,5-diazaspiro [3.4]octane-5-carboxylate (1621436-26-7) + tert-butyl (S)-2-((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)-1-oxo-2,5-diazaspiro[3.4]octane-5-carboxylate (1621435-14-0)

Guidance literature:

With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 16h; Overall yield = 1.15 g;

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → tert-butyl (S)-2-((2S,3R)-1,3-bis(benzyloxy)-1-oxobutan-2-yl)-1-oxo-2,5-diazaspiro[3.4]octane-5-carboxylate (1621435-14-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine / dichloromethane / 0.33 h / 0 °C / Inert atmosphere; Large scale

1.2: 8 h / 0 - 20 °C / Inert atmosphere; Large scale

2.1: sodium hydroxide; water / tetrahydrofuran; methanol / 6 h / 70 °C / Large scale

3.1: palladium 10% on activated carbon; hydrogen / methanol / 8 h / 20 °C

4.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.17 h / 0 - 5 °C / Inert atmosphere

4.2: 6 h / 0 - 20 °C / Inert atmosphere

5.1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 4 h / 15 - 20 °C / Inert atmosphere

With di-isopropyl azodicarboxylate; palladium 10% on activated carbon; water; hydrogen; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane;

upstream raw materials:

N‐(tert‐butoxycarbonyl)‐O‐benzyl‐L‐threonine benzyl ester

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

L-proline

(S)-N-(tert-butoxycarbonyl)proline methyl ester