(2S)-N-[2-acetamido-3-benzyloxy-6-[(S)-2-(tert-butoxycarbonyl)amino-3-hydroxypropyl]phenyl]valine methyl ester

Base Information

Chemical Name:(2S)-N-[2-acetamido-3-benzyloxy-6-[(S)-2-(tert-butoxycarbonyl)amino-3-hydroxypropyl]phenyl]valine methyl ester
CAS No.:247197-26-8
Molecular Formula:C₂₉H₄₁N₃O₇
Molecular Weight:543.66
Hs Code.:

Synonyms:(2S)-N-[2-acetamido-3-benzyloxy-6-[(S)-2-(tert-butoxycarbonyl)amino-3-hydroxypropyl]phenyl]valine methyl ester

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Chemical Property of (2S)-N-[2-acetamido-3-benzyloxy-6-[(S)-2-(tert-butoxycarbonyl)amino-3-hydroxypropyl]phenyl]valine methyl ester

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Technology Process of (2S)-N-[2-acetamido-3-benzyloxy-6-[(S)-2-(tert-butoxycarbonyl)amino-3-hydroxypropyl]phenyl]valine methyl ester

There total 15 articles about (2S)-N-[2-acetamido-3-benzyloxy-6-[(S)-2-(tert-butoxycarbonyl)amino-3-hydroxypropyl]phenyl]valine 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: 63.0%

: 148773-91-5
(R)-1-(methoxycarbonyl)-2-methylpropyl trifluoromethanesulfonate

: [2-(3-acetylamino-2-amino-4-benzyloxy-phenyl)-1-hydroxymethyl-ethyl]-carbamic acid tert-butyl ester

: 247197-26-8
(2S)-N-[2-acetamido-3-benzyloxy-6-[(S)-2-(tert-butoxycarbonyl)amino-3-hydroxypropyl]phenyl]valine methyl ester

Guidance literature:: With 2,6-dimethylpyridine; In 1,2-dichloro-ethane; at 70 ℃; for 72h;
DOI:10.1021/jo990605h

Reference yield:

: 1080-06-4
L-Tyr-OMe

: 247197-26-8
(2S)-N-[2-acetamido-3-benzyloxy-6-[(S)-2-(tert-butoxycarbonyl)amino-3-hydroxypropyl]phenyl]valine methyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: 100 percent / NaOH; NaHCO₃ / H₂O; CHCl₃ / 2 h

2.1: 85 percent / La(NO₃)2*6H₂O; NaNO₃; 6N HCl / CH₂Cl₂ / 6 h / 0 - 20 °C

3.1: H₂ / Pd/C / ethyl acetate / 22800 Torr

4.1: 80 percent / Et₃N / CH₂Cl₂ / 2 h / -10 °C

5.1: LiBH₄ / tetrahydrofuran / 5 h / 20 °C

6.1: 78 percent / pyridine / 8 h / 20 °C

7.1: 40 percent / HNO₃ / acetic anhydride / -13 °C

8.1: Na₂CO₃ / methanol; H₂O / 2 h

9.1: 79 percent / K₂CO₃ / dimethylformamide / 3 h / 50 °C

10.1: 10 percent KOH / methanol / 50 °C

10.2: 44 percent / NaHCO₃ / 32 h

11.1: Cu(OAc)2; NaBH₄ / methanol / 0.5 h / 0 °C

12.1: 63 percent / 2,6-lutidine / 1,2-dichloro-ethane / 72 h / 70 °C

With 2,6-dimethylpyridine; hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium nitrate; sodium tetrahydroborate; lithium borohydride; copper diacetate; lanthanum nitrate; hydrogen; nitric acid; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; water; acetic anhydride; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1.1: NH2-protection / 2.1: Nitration / 3.1: Reduction / 4.1: Acetylation / 5.1: Reduction / 6.1: Acetylation / 7.1: Nitration / 8.1: Deacetylation / 9.1: Substitution / 10.1: Hydrolysis / 10.2: NH2-protection / 11.1: Reduction / 12.1: Substitution;
DOI:10.1021/jo990605h

Reference yield:

: 60-18-4,18875-48-4,25619-78-7,30704-25-7
L-tyrosine

: 247197-26-8
(2S)-N-[2-acetamido-3-benzyloxy-6-[(S)-2-(tert-butoxycarbonyl)amino-3-hydroxypropyl]phenyl]valine methyl ester

Guidance literature:: Multi-step reaction with 13 steps

1.1: SOCl₂ / Heating

2.1: 100 percent / NaOH; NaHCO₃ / H₂O; CHCl₃ / 2 h

3.1: 85 percent / La(NO₃)2*6H₂O; NaNO₃; 6N HCl / CH₂Cl₂ / 6 h / 0 - 20 °C

4.1: H₂ / Pd/C / ethyl acetate / 22800 Torr

5.1: 80 percent / Et₃N / CH₂Cl₂ / 2 h / -10 °C

6.1: LiBH₄ / tetrahydrofuran / 5 h / 20 °C

7.1: 78 percent / pyridine / 8 h / 20 °C

8.1: 40 percent / HNO₃ / acetic anhydride / -13 °C

9.1: Na₂CO₃ / methanol; H₂O / 2 h

10.1: 79 percent / K₂CO₃ / dimethylformamide / 3 h / 50 °C

11.1: 10 percent KOH / methanol / 50 °C

11.2: 44 percent / NaHCO₃ / 32 h

12.1: Cu(OAc)2; NaBH₄ / methanol / 0.5 h / 0 °C

13.1: 63 percent / 2,6-lutidine / 1,2-dichloro-ethane / 72 h / 70 °C

With 2,6-dimethylpyridine; hydrogenchloride; potassium hydroxide; sodium hydroxide; sodium nitrate; sodium tetrahydroborate; lithium borohydride; thionyl chloride; copper diacetate; lanthanum nitrate; hydrogen; nitric acid; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; triethylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; dichloromethane; chloroform; water; acetic anhydride; ethyl acetate; 1,2-dichloro-ethane; N,N-dimethyl-formamide; 1.1: Esterification / 2.1: NH2-protection / 3.1: Nitration / 4.1: Reduction / 5.1: Acetylation / 6.1: Reduction / 7.1: Acetylation / 8.1: Nitration / 9.1: Deacetylation / 10.1: Substitution / 11.1: Hydrolysis / 11.2: NH2-protection / 12.1: Reduction / 13.1: Substitution;
DOI:10.1021/jo990605h