(S)-2-{(R)-2-[(S)-2-Amino-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-3-phenyl-propionylamino}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester

Base Information

• Chemical Name: (S)-2-{(R)-2-[(S)-2-Amino-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-3-phenyl-propionylamino}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester
• CAS No.: 184296-16-0
• Molecular Formula: C₂₈H₅₁N₃O₆Si₂
• Molecular Weight: 581.9

Synonyms:(S)-2-{(R)-2-[(S)-2-Amino-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-3-phenyl-propionylamino}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester

Chemical Property of (S)-2-{(R)-2-[(S)-2-Amino-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-3-phenyl-propionylamino}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester

Chemical Property:

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Technology Process of (S)-2-{(R)-2-[(S)-2-Amino-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-3-phenyl-propionylamino}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester

There total 8 articles about (S)-2-{(R)-2-[(S)-2-Amino-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-3-phenyl-propionylamino}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid 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:

Cbz-D-Phe (2448-45-5) → (S)-2-{(R)-2-[(S)-2-Amino-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-3-phenyl-propionylamino}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester (184296-16-0)

Guidance literature:

Multi-step reaction with 7 steps

1: N-methylmorpholine / CH₂Cl₂ / 0.25 h / -15 °C

2: CH₂Cl₂ / 0 - 20 °C

3: imidazole / CH₂Cl₂

4: H₂ / Pd/C / methanol

5: CH₂Cl₂ / 0 - 20 °C

6: imidazole / CH₂Cl₂

7: H₂ / Pd/C / methanol / 2 h

With 4-methyl-morpholine; 1H-imidazole; hydrogen; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/ja962859f

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (S)-2-{(R)-2-[(S)-2-Amino-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-3-phenyl-propionylamino}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester (184296-16-0)

Guidance literature:

Multi-step reaction with 5 steps

1: imidazole / CH₂Cl₂

2: H₂ / Pd/C / methanol

3: CH₂Cl₂ / 0 - 20 °C

4: imidazole / CH₂Cl₂

5: H₂ / Pd/C / methanol / 2 h

With 1H-imidazole; hydrogen; palladium on activated charcoal; In methanol; dichloromethane;

DOI:10.1021/ja962859f

Reference yield:

(S)-2-{(R)-2-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-3-phenyl-propionylamino}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester (184295-95-2) → (S)-2-{(R)-2-[(S)-2-Amino-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-3-phenyl-propionylamino}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester (184296-16-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 2h;

DOI:10.1021/ja962859f

upstream raw materials:

(S)-2-{(R)-2-[(S)-2-Benzyloxycarbonylamino-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-3-phenyl-propionylamino}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester

Z-D-Phe-Ser-OMe

Cbz-D-Phe

C₂₂H₂₅NO₆

Downstream raw materials:

(S)-2-{(R)-2-[(S)-2-((R)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-3-phenyl-propionylamino}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid methyl ester

(5S,8S,11R,14S,17R,20S,22aS)-5,11-Dibenzyl-20-((S)-1-hydroxy-ethyl)-8,14-bis-hydroxymethyl-17-isopropyl-hexadecahydro-3a,6,9,12,15,18,21-heptaaza-cyclopentacyclohenicosene-4,7,10,13,16,19,22-heptaone

(S)-2-{(R)-2-[(S)-2-((R)-2-Benzyloxycarbonylamino-3-methyl-butyrylamino)-3-(tert-butyl-dimethyl-silanyloxy)-propionylamino]-3-phenyl-propionylamino}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid

cyclo[D-Val-Ser(oxaz)-D-Phe-Ser(oxaz)-Phe-Pro-Allo-Thr(oxaz)]

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