Glycine, L-2-[3-methoxy-5-[2-methoxy-5-[2-oxo-1-[(phenylmethylene)amino]-2-[2- (trimethylsilyl)ethoxy]ethyl]phenoxy]phenyl]-N-[N-[(phenylmethoxy)carbon yl]-D-tyrosyl]-, ethyl ester, (R)-

Base Information

• Chemical Name: Glycine, L-2-[3-methoxy-5-[2-methoxy-5-[2-oxo-1-[(phenylmethylene)amino]-2-[2- (trimethylsilyl)ethoxy]ethyl]phenoxy]phenyl]-N-[N-[(phenylmethoxy)carbon yl]-D-tyrosyl]-, ethyl ester, (R)-
• CAS No.: 143145-67-9
• Molecular Formula: C₄₉H₅₅N₃O₁₁Si
• Molecular Weight: 890.075

Synonyms:

Chemical Property of Glycine, L-2-[3-methoxy-5-[2-methoxy-5-[2-oxo-1-[(phenylmethylene)amino]-2-[2- (trimethylsilyl)ethoxy]ethyl]phenoxy]phenyl]-N-[N-[(phenylmethoxy)carbon yl]-D-tyrosyl]-, ethyl ester, (R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Glycine, L-2-[3-methoxy-5-[2-methoxy-5-[2-oxo-1-[(phenylmethylene)amino]-2-[2- (trimethylsilyl)ethoxy]ethyl]phenoxy]phenyl]-N-[N-[(phenylmethoxy)carbon yl]-D-tyrosyl]-, ethyl ester, (R)-

There total 19 articles about Glycine, L-2-[3-methoxy-5-[2-methoxy-5-[2-oxo-1-[(phenylmethylene)amino]-2-[2- (trimethylsilyl)ethoxy]ethyl]phenoxy]phenyl]-N-[N-[(phenylmethoxy)carbon yl]-D-tyrosyl]-, ethyl ester, (R)- 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:

N--D-tyrosyl>-(S)-α-amino-3-<5--(R)-α-amino-α-<<<(trimethylsilyl)ethyl>oxy>carbonyl>methyl>-2-methoxyphenoxy>-5-methoxybenzeneacetic acid ethyl ester (143145-66-8) → (S)-[(R)-3-(4-Hydroxy-phenyl)-2-(2-phenoxy-acetylamino)-propionylamino]-(3-methoxy-5-{2-methoxy-5-[(R)-{[1-phenyl-meth-(E)-ylidene]-amino}-(2-trimethylsilanyl-ethoxycarbonyl)-methyl]-phenoxy}-phenyl)-acetic acid ethyl ester (143145-67-9)

Guidance literature:

With lead(IV) acetate; In methanol; dichloromethane; for 0.0833333h; ice-cold;

DOI:10.1021/jo00046a031

Reference yield:

1-carbomethoxy-3,5-dihydroxybenzene (2150-44-9) → (S)-[(R)-3-(4-Hydroxy-phenyl)-2-(2-phenoxy-acetylamino)-propionylamino]-(3-methoxy-5-{2-methoxy-5-[(R)-{[1-phenyl-meth-(E)-ylidene]-amino}-(2-trimethylsilanyl-ethoxycarbonyl)-methyl]-phenoxy}-phenyl)-acetic acid ethyl ester (143145-67-9)

Guidance literature:

Multi-step reaction with 16 steps

1: 65 percent / K₂CO₃, Bu₄NI / acetone / 3 h / Heating

2: 1) NaH / 1) DMF, r.t., 0.5 h, 2) 90 deg C, 3 h

3: 95 percent / boron trifluoride etherate / CH₂Cl₂ / 0.5 h / Ambient temperature

4: 1) DIBALH, 2) 1N HCl / 1) a) CH₂Cl₂, -78 deg C, 0.5 h, 2) MeOH, 0 deg C, 0.5 h

5: 86 percent / pyridinium chlorochromate / CH₂Cl₂ / 1 h / 0 °C

6: CHCl₃ / 5 h / Ambient temperature

7: methanol / 3 h

8: 90 percent / ethereal HCl / 5 h / Ambient temperature

9: lead tetraacetate / CH₂Cl₂; methanol / 0.08 h / 0 °C / 1) CH₂Cl₂, MeOH, 0 deg C, 5 min, 2) phosphate buffer pH 7, r.t., 0.5 h

10: 3N HCl / diethyl ether / 0.25 h / Ambient temperature

11: 1) 1-hydroxybenzotriazole hydrate, 1,3-dicyclohexylcarbodiimide / 1) DMF, 0 deg C, 30 min, 2) DMF, 0 deg C to r.t., 1,5 h

12: 85 percent / mercuric oxide, mercuric chloride / acetonitrile; H₂O / 2 h / Ambient temperature

13: CHCl₃ / 24 h / Ambient temperature

14: CHCl₃ / 24 h / Ambient temperature

15: 52 percent / ethereal HCl / CHCl₃ / 3 h / Ambient temperature

16: lead tetraacetate / CH₂Cl₂; methanol / 0.08 h / ice-cold

With lead(IV) acetate; hydrogenchloride; methanol; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; pyridinium chlorochromate; mercury dichloride; mercury(II) oxide; In methanol; diethyl ether; dichloromethane; chloroform; water; acetone; acetonitrile;

DOI:10.1021/jo00046a031

Reference yield:

3,5-Dihydroxybenzoic acid (99-10-5) → (S)-[(R)-3-(4-Hydroxy-phenyl)-2-(2-phenoxy-acetylamino)-propionylamino]-(3-methoxy-5-{2-methoxy-5-[(R)-{[1-phenyl-meth-(E)-ylidene]-amino}-(2-trimethylsilanyl-ethoxycarbonyl)-methyl]-phenoxy}-phenyl)-acetic acid ethyl ester (143145-67-9)

Guidance literature:

Multi-step reaction with 17 steps

1: 96 percent / conc. H₂SO₄ / 5 h / Heating

2: 65 percent / K₂CO₃, Bu₄NI / acetone / 3 h / Heating

3: 1) NaH / 1) DMF, r.t., 0.5 h, 2) 90 deg C, 3 h

4: 95 percent / boron trifluoride etherate / CH₂Cl₂ / 0.5 h / Ambient temperature

5: 1) DIBALH, 2) 1N HCl / 1) a) CH₂Cl₂, -78 deg C, 0.5 h, 2) MeOH, 0 deg C, 0.5 h

6: 86 percent / pyridinium chlorochromate / CH₂Cl₂ / 1 h / 0 °C

7: CHCl₃ / 5 h / Ambient temperature

8: methanol / 3 h

9: 90 percent / ethereal HCl / 5 h / Ambient temperature

10: lead tetraacetate / CH₂Cl₂; methanol / 0.08 h / 0 °C / 1) CH₂Cl₂, MeOH, 0 deg C, 5 min, 2) phosphate buffer pH 7, r.t., 0.5 h

11: 3N HCl / diethyl ether / 0.25 h / Ambient temperature

12: 1) 1-hydroxybenzotriazole hydrate, 1,3-dicyclohexylcarbodiimide / 1) DMF, 0 deg C, 30 min, 2) DMF, 0 deg C to r.t., 1,5 h

13: 85 percent / mercuric oxide, mercuric chloride / acetonitrile; H₂O / 2 h / Ambient temperature

14: CHCl₃ / 24 h / Ambient temperature

15: CHCl₃ / 24 h / Ambient temperature

16: 52 percent / ethereal HCl / CHCl₃ / 3 h / Ambient temperature

17: lead tetraacetate / CH₂Cl₂; methanol / 0.08 h / ice-cold

With lead(IV) acetate; hydrogenchloride; methanol; sulfuric acid; boron trifluoride diethyl etherate; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; potassium carbonate; 1-hydroxybenzotriazol-hydrate; dicyclohexyl-carbodiimide; pyridinium chlorochromate; mercury dichloride; mercury(II) oxide; In methanol; diethyl ether; dichloromethane; chloroform; water; acetone; acetonitrile;

DOI:10.1021/jo00046a031

upstream raw materials:

N--D-tyrosyl>-(S)-α-amino-3-<5--(R)-α-amino-α-<<<(trimethylsilyl)ethyl>oxy>carbonyl>methyl>-2-methoxyphenoxy>-5-methoxybenzeneacetic acid ethyl ester

1-carbomethoxy-3,5-dihydroxybenzene

3,5-Dihydroxybenzoic acid

3-hydroxy-5-methoxy-benzoic acid methyl ester

Downstream raw materials:

N--D-tyrosyl>-(S)-α-amino-3-<5-<(R)-amino<<<(trimethylsilyl)ethyl>oxy>carbonyl>methyl>-2-methoxyphenoxy>-5-methoxybenzeneacetic acid ethyl ester

(8S,11R,14R)-14-tert-Butoxycarbonylamino-11-(4-hydroxy-benzyl)-5,18-dimethoxy-10,13-dioxo-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁹⁾,3,5,7⁽²⁰⁾,15,17-hexaene-8-carboxylic acid ethyl ester

N--D-tyrosyl>-(S)-α-amino-3-<5-<(R)-N-<(1,1-dimethylethoxy)carbonyl>aminocarboxymethyl>-2-methoxyphenoxy>-5-methoxybenzeneacetic acid ethyl ester

N--D-tyrosyl>-(S)-α-amino-3-<5-<(R)-N-<(1,1-dimethylethoxy)carbonyl>amino<<<(trimethylsilyl)ethyl>oxy>carbonyl>methyl>-2-methoxyphenoxy>-5-methoxybenzeneacetic acid ethyl ester

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