tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-((tert-butyldimethylsilyl)oxy)butanoate

Base Information

• Chemical Name: tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-((tert-butyldimethylsilyl)oxy)butanoate
• CAS No.: 299926-04-8
• Molecular Formula: C₂₂H₃₇NO₅Si
• Molecular Weight: 423.625

Synonyms:tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-((tert-butyldimethylsilyl)oxy)butanoate

Chemical Property of tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-((tert-butyldimethylsilyl)oxy)butanoate

Chemical Property:

Purity/Quality:

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Technology Process of tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-((tert-butyldimethylsilyl)oxy)butanoate

There total 3 articles about tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-((tert-butyldimethylsilyl)oxy)butanoate 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: 97.0%

tert-butyldimethylsilyl chloride (18162-48-6) + tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-hydroxybutanoate (203064-74-8) → tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-((tert-butyldimethylsilyl)oxy)butanoate (299926-04-8)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 25 ℃; for 20h;

DOI:10.1055/s-2000-6417

Reference yield:

tert-butyl (E)-crotonate (79218-15-8) → tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-((tert-butyldimethylsilyl)oxy)butanoate (299926-04-8)

Guidance literature:

Multi-step reaction with 2 steps

1: (DHQ)2PHAL; aq. K₂OsO₂(OH)4 / acetonitrile

2: 97 percent / imidazole / dimethylformamide / 20 h / 25 °C

With 1H-imidazole; Hydroquinone 1,4-phthalazinediyl diether; potassium dioxotetrahydroxoosmate(VI); In N,N-dimethyl-formamide; acetonitrile; 1: Addition / 2: Substitution;

DOI:10.1055/s-2000-6417

Reference yield:

benzyl N-chlorocarbamate (30830-47-8) → tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-((tert-butyldimethylsilyl)oxy)butanoate (299926-04-8)

Guidance literature:

Multi-step reaction with 2 steps

1: (DHQ)2PHAL; aq. K₂OsO₂(OH)4 / acetonitrile

2: 97 percent / imidazole / dimethylformamide / 20 h / 25 °C

With 1H-imidazole; Hydroquinone 1,4-phthalazinediyl diether; potassium dioxotetrahydroxoosmate(VI); In N,N-dimethyl-formamide; acetonitrile; 1: Addition / 2: Substitution;

DOI:10.1055/s-2000-6417

upstream raw materials:

tert-butyldimethylsilyl chloride

tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)amino)-2-hydroxybutanoate

tert-butyl (E)-crotonate

benzyl N-chlorocarbamate

Downstream raw materials:

(2R,3S)-tert-Butyl 2-tert-butyldimethylsilyloxy-3-(N-benzyloxycarbonyl-N-methyl)aminobutanoate

(1R,2S)-2-(N-Benzyloxycarbonyl-N-methyl)amino-1-(tert-butoxycarbonyl)propyl-1-methanesulfonate

tert-butyl (2S,3S)-2-azido-3-(((benzyloxy)carbonyl)(methyl)amino)butanoate

tert-butyl (2R,3S)-3-(((benzyloxy)carbonyl)(methyl)amino)-2-hydroxybutanoate

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