(4S,5S)-[4',4',4'-⁽²⁾H₃]-N-tert-butoxycarbonyl-5-tert-butyldiphenylsiloxymethyl-4-methylpyrrolidin-2-one

Base Information

• Chemical Name: (4S,5S)-[4',4',4'-⁽²⁾H₃]-N-tert-butoxycarbonyl-5-tert-butyldiphenylsiloxymethyl-4-methylpyrrolidin-2-one
• CAS No.: 713526-43-3
• Molecular Formula: C₂₇H₃₇NO₄Si
• Molecular Weight: 470.657

Synonyms:(4S,5S)-[4',4',4'-⁽²⁾H₃]-N-tert-butoxycarbonyl-5-tert-butyldiphenylsiloxymethyl-4-methylpyrrolidin-2-one

Chemical Property of (4S,5S)-[4',4',4'-⁽²⁾H₃]-N-tert-butoxycarbonyl-5-tert-butyldiphenylsiloxymethyl-4-methylpyrrolidin-2-one

Chemical Property:

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Technology Process of (4S,5S)-[4',4',4'-⁽²⁾H₃]-N-tert-butoxycarbonyl-5-tert-butyldiphenylsiloxymethyl-4-methylpyrrolidin-2-one

There total 1 articles about (4S,5S)-[4',4',4'-⁽²⁾H₃]-N-tert-butoxycarbonyl-5-tert-butyldiphenylsiloxymethyl-4-methylpyrrolidin-2-one 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%

methyl-d3-magnesium iodide (41251-37-0) + (S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (138871-58-6) → (4S,5S)-[4',4',4'-(2)H3]-N-tert-butoxycarbonyl-5-tert-butyldiphenylsiloxymethyl-4-methylpyrrolidin-2-one (713526-43-3)

Guidance literature:

methyl-d3-magnesium iodide; With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; diethyl ether; at -15 ℃; for 0.25h;

(S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester; With chloro-trimethyl-silane; In tetrahydrofuran; diethyl ether; at -78 ℃; for 1h;

DOI:10.1039/b401646g

Reference yield: 98.0%

(4S,5S)-[4',4',4'-(2)H3]-N-tert-butoxycarbonyl-5-tert-butyldiphenylsiloxymethyl-4-methylpyrrolidin-2-one (713526-43-3) → (3S,4S)-[3',3',3'-(2)H3]-4-tert-butoxycarbonylamino-5-tert-butyldiphenylsilyloxy-3-methylpentanoic acid (713526-44-4)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; at 20 ℃;

DOI:10.1039/b401646g

Reference yield:

(4S,5S)-[4',4',4'-(2)H3]-N-tert-butoxycarbonyl-5-tert-butyldiphenylsiloxymethyl-4-methylpyrrolidin-2-one (713526-43-3) → (2S,3R)-[3',3',3'-(2)H3]-2-tert-butoxycarbonylamino-O-tert-butyldiphenylsilyl-3-methylbutan-1-ol (713526-45-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 98 percent / aq. LiOH / tetrahydrofuran / 20 °C

2.1: N-methylmorpholine / tetrahydrofuran / 0.25 h / -15 °C

3.1: Et₃N; N-hydroxy-2-thiopyridone / tetrahydrofuran / 1 h

3.2: 1.247 g / tert-butylthiol / tetrahydrofuran / 1 h / 20 °C / Irradiation

With 4-methyl-morpholine; 1-hydroxy-2(1H)-pyridinethione; lithium hydroxide; triethylamine; In tetrahydrofuran;

DOI:10.1039/b401646g

upstream raw materials:

methyl-d3-magnesium iodide

(S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester

Downstream raw materials:

(3S,4S)-[3',3',3'-⁽²⁾H₃]-4-tert-butoxycarbonylamino-5-tert-butyldiphenylsilyloxy-3-methylpentanoic acid

(2S,3R)-[3',3',3'-⁽²⁾H₃]-2-tert-butoxycarbonylamino-O-tert-butyldiphenylsilyl-3-methylbutan-1-ol

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