(2S,4R)-2-Methyl-4-((R)-2-methyl-propane-2-sulfinylamino)-5-phenyl-pentanoic acid methyl ester

Base Information

• Chemical Name: (2S,4R)-2-Methyl-4-((R)-2-methyl-propane-2-sulfinylamino)-5-phenyl-pentanoic acid methyl ester
• CAS No.: 921927-86-8
• Molecular Formula: C₁₇H₂₇NO₃S
• Molecular Weight: 325.472

Synonyms:(2S,4R)-2-Methyl-4-((R)-2-methyl-propane-2-sulfinylamino)-5-phenyl-pentanoic acid methyl ester

Chemical Property of (2S,4R)-2-Methyl-4-((R)-2-methyl-propane-2-sulfinylamino)-5-phenyl-pentanoic acid methyl ester

Chemical Property:

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Technology Process of (2S,4R)-2-Methyl-4-((R)-2-methyl-propane-2-sulfinylamino)-5-phenyl-pentanoic acid methyl ester

There total 2 articles about (2S,4R)-2-Methyl-4-((R)-2-methyl-propane-2-sulfinylamino)-5-phenyl-pentanoic acid methyl ester 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: 55.0%

methacrylic acid methyl ester (80-62-6,114512-63-9,143476-91-9,25188-98-1,9011-14-7) + (N(E),R)-2-methyl-N-(2-phenylethylidene)-2-propanesulfinamide (221375-48-0) → (2S,4R)-2-Methyl-4-((R)-2-methyl-propane-2-sulfinylamino)-5-phenyl-pentanoic acid methyl ester (921927-86-8) + (2R,4R)-2-Methyl-4-((R)-2-methyl-propane-2-sulfinylamino)-5-phenyl-pentanoic acid methyl ester + (2S,4S)-2-Methyl-4-((R)-2-methyl-propane-2-sulfinylamino)-5-phenyl-pentanoic acid methyl ester + (2R,4S)-2-Methyl-4-((R)-2-methyl-propane-2-sulfinylamino)-5-phenyl-pentanoic acid methyl ester

Guidance literature:

With samarium diiodide; water; lithium bromide; In tetrahydrofuran; at -78 ℃; for 12h;

DOI:10.1021/ja067177z

Reference yield:

phenylacetaldehyde (122-78-1) → (2S,4R)-2-Methyl-4-((R)-2-methyl-propane-2-sulfinylamino)-5-phenyl-pentanoic acid methyl ester (921927-86-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 55 percent / SmI₂; LiBr; H₂O / tetrahydrofuran / 12 h / -78 °C

With samarium diiodide; water; lithium bromide; In tetrahydrofuran;

DOI:10.1021/ja067177z

Reference yield: 100.0%

(2S,4R)-2-Methyl-4-((R)-2-methyl-propane-2-sulfinylamino)-5-phenyl-pentanoic acid methyl ester (921927-86-8) → (2S,4R)-4-amino-2-methyl-5-phenylpentanoic acid hydrochloride

Guidance literature:

With hydrogenchloride; at 100 ℃; for 1h;

DOI:10.1021/ja067177z

upstream raw materials:

methacrylic acid methyl ester

(N(E),R)-2-methyl-N-(2-phenylethylidene)-2-propanesulfinamide

phenylacetaldehyde

Downstream raw materials:

desacetyl tubulysin D

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