methyl (S)-2-[N-allyl-3-(4-benzyloxyphenyl)acetamido]-5-(triisopropylsilyloxy)pentanoate

Base Information

Chemical Name:methyl (S)-2-[N-allyl-3-(4-benzyloxyphenyl)acetamido]-5-(triisopropylsilyloxy)pentanoate
CAS No.:945493-39-0
Molecular Formula:C₃₃H₄₉NO₅Si
Molecular Weight:567.841
Hs Code.:

Synonyms:methyl (S)-2-[N-allyl-3-(4-benzyloxyphenyl)acetamido]-5-(triisopropylsilyloxy)pentanoate

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Chemical Property of methyl (S)-2-[N-allyl-3-(4-benzyloxyphenyl)acetamido]-5-(triisopropylsilyloxy)pentanoate

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Technology Process of methyl (S)-2-[N-allyl-3-(4-benzyloxyphenyl)acetamido]-5-(triisopropylsilyloxy)pentanoate

There total 12 articles about methyl (S)-2-[N-allyl-3-(4-benzyloxyphenyl)acetamido]-5-(triisopropylsilyloxy)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: 86.0%

: 945492-92-2
methyl (S)-2-(N-allylamino)-5-(triisopropylsilyloxy)pentanoate

: 6547-53-1
2-[4-(benzyloxy)benzyl]acetic acid

: 945493-39-0
methyl (S)-2-[N-allyl-3-(4-benzyloxyphenyl)acetamido]-5-(triisopropylsilyloxy)pentanoate

Guidance literature:: With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20 ℃; for 3h;
DOI:10.1039/b702649h

Reference yield:

: 56-86-0,21675-62-7,23009-64-5,25104-13-6,84960-48-5,25513-46-6
L-glutamic acid

: 945493-39-0
methyl (S)-2-[N-allyl-3-(4-benzyloxyphenyl)acetamido]-5-(triisopropylsilyloxy)pentanoate

Guidance literature:: Multi-step reaction with 11 steps

1.1: H₂SO₄

1.2: pyridine / ethanol

2.1: triethylamine / dimethylformamide

3.1: potassium carbonate / dimethylformamide

4.1: 42 g / H₂ / Pd/C / ethanol

5.1: triethylamine

6.1: NaBH₄ / methanol; tetrahydrofuran

7.1: triethylamine / dimethylformamide / 5 h / 20 °C

7.2: TFA / CH₂Cl₂ / 1 h / 0 °C

8.1: 4.95 g / triethylamine / CH₂Cl₂

9.1: 82 percent / potassium carbonate / dimethylformamide / 3 h / 20 °C

10.1: 90 percent / mercaptoacetic acid; LiOH*H₂O / dimethylformamide / 1 h / 20 °C

11.1: 86 percent / HATU; triethylamine / dimethylformamide / 3 h / 20 °C

With lithium hydroxide; sodium tetrahydroborate; sulfuric acid; hydrogen; potassium carbonate; mercaptoacetic acid; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/b702649h

Reference yield:

: 1676-73-9,25014-27-1
L-glutamic acid γ-benzyl ester

: 945493-39-0
methyl (S)-2-[N-allyl-3-(4-benzyloxyphenyl)acetamido]-5-(triisopropylsilyloxy)pentanoate

Guidance literature:: Multi-step reaction with 10 steps

1.1: triethylamine / dimethylformamide

2.1: potassium carbonate / dimethylformamide

3.1: 42 g / H₂ / Pd/C / ethanol

4.1: triethylamine

5.1: NaBH₄ / methanol; tetrahydrofuran

6.1: triethylamine / dimethylformamide / 5 h / 20 °C

6.2: TFA / CH₂Cl₂ / 1 h / 0 °C

7.1: 4.95 g / triethylamine / CH₂Cl₂

8.1: 82 percent / potassium carbonate / dimethylformamide / 3 h / 20 °C

9.1: 90 percent / mercaptoacetic acid; LiOH*H₂O / dimethylformamide / 1 h / 20 °C

10.1: 86 percent / HATU; triethylamine / dimethylformamide / 3 h / 20 °C

With lithium hydroxide; sodium tetrahydroborate; hydrogen; potassium carbonate; mercaptoacetic acid; triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/b702649h