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

Base Information

• Chemical Name: (3S,4S)-[3',3',3'-⁽²⁾H₃]-4-tert-butoxycarbonylamino-5-tert-butyldiphenylsilyloxy-3-methylpentanoic acid
• CAS No.: 713526-44-4
• Molecular Formula: C₂₇H₃₉NO₅Si
• Molecular Weight: 488.672

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

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

Chemical Property:

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

There total 2 articles about (3S,4S)-[3',3',3'-⁽²⁾H₃]-4-tert-butoxycarbonylamino-5-tert-butyldiphenylsilyloxy-3-methylpentanoic acid 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: 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:

(S)-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-oxo-2,5-dihydro-pyrrole-1-carboxylic acid tert-butyl ester (138871-58-6) → (3S,4S)-[3',3',3'-(2)H3]-4-tert-butoxycarbonylamino-5-tert-butyldiphenylsilyloxy-3-methylpentanoic acid (713526-44-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: CuBr*SMe₂ / tetrahydrofuran; diethyl ether / 0.25 h / -15 °C

1.2: 89 percent / TMSCl / tetrahydrofuran; diethyl ether / 1 h / -78 °C

2.1: 98 percent / aq. LiOH / tetrahydrofuran / 20 °C

With lithium hydroxide; copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; diethyl ether;

DOI:10.1039/b401646g

Reference yield:

isobutyl chloroformate (543-27-1) + (3S,4S)-[3',3',3'-(2)H3]-4-tert-butoxycarbonylamino-5-tert-butyldiphenylsilyloxy-3-methylpentanoic acid (713526-44-4) → C32H44(2)H3NO7Si

Guidance literature:

With 4-methyl-morpholine; In tetrahydrofuran; at -15 ℃; for 0.25h;

DOI:10.1039/b401646g

upstream raw materials:

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

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

Downstream raw materials:

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

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