methyl (3R_.5R)-3-(N-tert-butyloxycarbonyl-N-benzyl)amino-5-(tert-butyldimethylsiloxy)hexanoate

Base Information

• Chemical Name: methyl (3R_.5R)-3-(N-tert-butyloxycarbonyl-N-benzyl)amino-5-(tert-butyldimethylsiloxy)hexanoate
• CAS No.: 341544-19-2
• Molecular Formula: C₂₅H₄₃NO₅Si
• Molecular Weight: 465.706

Synonyms:methyl (3R_.5R)-3-(N-tert-butyloxycarbonyl-N-benzyl)amino-5-(tert-butyldimethylsiloxy)hexanoate

Chemical Property of methyl (3R_.5R)-3-(N-tert-butyloxycarbonyl-N-benzyl)amino-5-(tert-butyldimethylsiloxy)hexanoate

Chemical Property:

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Technology Process of methyl (3R_.5R)-3-(N-tert-butyloxycarbonyl-N-benzyl)amino-5-(tert-butyldimethylsiloxy)hexanoate

There total 4 articles about methyl (3R_.5R)-3-(N-tert-butyloxycarbonyl-N-benzyl)amino-5-(tert-butyldimethylsiloxy)hexanoate 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)-5-(tert-butyl-dimethyl-silanyloxy)-hexanoic acid + methyl iodide (74-88-4) → methyl (3R.5R)-3-(N-tert-butyloxycarbonyl-N-benzyl)amino-5-(tert-butyldimethylsiloxy)hexanoate (341544-19-2)

Guidance literature:

With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 12h;

DOI:10.1021/ja004140k

Reference yield:

benzyl-[3-(tert-butyl-dimethyl-silanyloxy)-1-(2-oxo-ethyl)-butyl]-carbamic acid tert-butyl ester → methyl (3R.5R)-3-(N-tert-butyloxycarbonyl-N-benzyl)amino-5-(tert-butyldimethylsiloxy)hexanoate (341544-19-2)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; sodium hydrogencarbonate; In N,N-dimethyl-formamide; tert-butyl alcohol;

DOI:10.1021/ja004140k

Reference yield:

(E)-(4S,6R)-6-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexyl]oxy-1-heptene (341544-08-9) → methyl (3R.5R)-3-(N-tert-butyloxycarbonyl-N-benzyl)amino-5-(tert-butyldimethylsiloxy)hexanoate (341544-19-2)

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

upstream raw materials:

methyl iodide

(E)-(4S,6R)-6-(tert-butyldimethylsilyl)oxy-4-benzylamino-1-[(1R,2R)-2-hydroxy-1,2-dicyclohexyl]oxy-1-heptene

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