methyl (3R,4S)-3-(N-tert-butyloxycarbonyl-N-benzyl)amino-4-(tert-butyldimethylsiloxy)pentanoate

Base Information

Chemical Name:methyl (3R,4S)-3-(N-tert-butyloxycarbonyl-N-benzyl)amino-4-(tert-butyldimethylsiloxy)pentanoate
CAS No.:341544-15-8
Molecular Formula:C₂₄H₄₁NO₅Si
Molecular Weight:451.679
Hs Code.:

Synonyms:methyl (3R,4S)-3-(N-tert-butyloxycarbonyl-N-benzyl)amino-4-(tert-butyldimethylsiloxy)pentanoate

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Chemical Property of methyl (3R,4S)-3-(N-tert-butyloxycarbonyl-N-benzyl)amino-4-(tert-butyldimethylsiloxy)pentanoate

Chemical Property:

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Technology Process of methyl (3R,4S)-3-(N-tert-butyloxycarbonyl-N-benzyl)amino-4-(tert-butyldimethylsiloxy)pentanoate

There total 6 articles about methyl (3R,4S)-3-(N-tert-butyloxycarbonyl-N-benzyl)amino-4-(tert-butyldimethylsiloxy)pentanoate 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:

: 3-(benzyl-tert-butoxycarbonyl-amino)-4-(tert-butyl-dimethyl-silanyloxy)-pentanoic acid

: 74-88-4
methyl iodide

: 341544-15-8
methyl (3R,4S)-3-(N-tert-butyloxycarbonyl-N-benzyl)amino-4-(tert-butyldimethylsiloxy)pentanoate

Guidance literature:: With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 12h;
DOI:10.1021/ja004140k

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 341544-15-8
methyl (3R,4S)-3-(N-tert-butyloxycarbonyl-N-benzyl)amino-4-(tert-butyldimethylsiloxy)pentanoate

Guidance literature:: Multi-step reaction with 4 steps

1.1: Et₃N / tetrahydrofuran / 12 h / 50 °C

2.1: O₃ / CH₂Cl₂ / -78 °C

2.2: dimethyl sulfide / CH₂Cl₂ / 12 h / -78 - 20 °C

3.1: NaClO₂; aq. NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 20 °C

4.1: NaHCO₃ / dimethylformamide / 12 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium hydrogencarbonate; ozone; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ja004140k

Reference yield:

: 184047-86-7
Benzyl-[(S)-2-(tert-butyl-dimethyl-silanyloxy)-prop-(E)-ylidene]-amine

: 341544-15-8
methyl (3R,4S)-3-(N-tert-butyloxycarbonyl-N-benzyl)amino-4-(tert-butyldimethylsiloxy)pentanoate

Guidance literature:: Multi-step reaction with 5 steps

1.1: Ti(O-i-Pr)4; i-PrMgCl / diethyl ether / 1.5 h / -50 - -40 °C

1.2: 83 percent / diethyl ether / 4 h / -40 - 20 °C

2.1: Et₃N / tetrahydrofuran / 12 h / 50 °C

3.1: O₃ / CH₂Cl₂ / -78 °C

3.2: dimethyl sulfide / CH₂Cl₂ / 12 h / -78 - 20 °C

4.1: NaClO₂; aq. NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol / 20 °C

5.1: NaHCO₃ / dimethylformamide / 12 h / 20 °C

With titanium(IV) isopropylate; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; isopropylmagnesium chloride; sodium hydrogencarbonate; ozone; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ja004140k