N^α-(tert-butoxycarbonyl)-C-(4-O-acetyl-α-L-rhamnopyranosyl)-L-tyrosine benzyl ester

Base Information

• Chemical Name: N^α-(tert-butoxycarbonyl)-C-(4-O-acetyl-α-L-rhamnopyranosyl)-L-tyrosine benzyl ester
• CAS No.: 239806-33-8
• Molecular Formula: C₃₀H₃₉NO₉
• Molecular Weight: 557.641

Synonyms:N^α-(tert-butoxycarbonyl)-C-(4-O-acetyl-α-L-rhamnopyranosyl)-L-tyrosine benzyl ester

Chemical Property of N^α-(tert-butoxycarbonyl)-C-(4-O-acetyl-α-L-rhamnopyranosyl)-L-tyrosine benzyl ester

Chemical Property:

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Technology Process of N^α-(tert-butoxycarbonyl)-C-(4-O-acetyl-α-L-rhamnopyranosyl)-L-tyrosine benzyl ester

There total 4 articles about N^α-(tert-butoxycarbonyl)-C-(4-O-acetyl-α-L-rhamnopyranosyl)-L-tyrosine benzyl 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: 58.0%

Nα-(tert-butoxycarbonyl)-C-(4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranosyl)-L-tyrosine benzyl ester (239806-32-7) → Nα-(tert-butoxycarbonyl)-C-(4-O-acetyl-α-L-rhamnopyranosyl)-L-tyrosine benzyl ester (239806-33-8)

Guidance literature:

With 4-methylmorpholine N-oxide; osmium(VIII) oxide; In water; acetone; tert-butyl alcohol; at 20 ℃; for 24h;

DOI:10.1021/jo990253e

Reference yield:

1-bromomethyl-4-iodobenzene (16004-15-2) → Nα-(tert-butoxycarbonyl)-C-(4-O-acetyl-α-L-rhamnopyranosyl)-L-tyrosine benzyl ester (239806-33-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: zinc; 1,2-dibromoethane; TMSCl / tetrahydrofuran / 1 h / 0 °C

1.2: BF₃*OEt₂ / CH₂Cl₂ / 0.25 h / 0 °C

2.1: zinc; 1,2-dibromoethane; TMSCl / tetrahydrofuran / 2 h / 35 °C

2.2: 83 percent / bis(tri-o-tolylphosphine)palladium dichloride / N,N-dimethyl-acetamide; tetrahydrofuran / 3 h / 20 - 50 °C

3.1: 58 percent / N-methylmorpholine N-oxide / OsO₄ / 2-methyl-propan-2-ol; acetone; H₂O / 24 h / 20 °C

With chloro-trimethyl-silane; 4-methylmorpholine N-oxide; ethylene dibromide; zinc; osmium(VIII) oxide; In tetrahydrofuran; water; acetone; tert-butyl alcohol; 1.1: Metallation / 1.2: C-glycosylation / 2.1: Metallation / 2.2: Alkylation / 3.1: Oxidation;

DOI:10.1021/jo990253e

Reference yield:

4'-(5-O-acetyl-2,6-anhydro-1,3,4,7-tetradeoxy-α-L-erythro-hept-3-enitol-1-yl)iodobenzene (239806-31-6) → Nα-(tert-butoxycarbonyl)-C-(4-O-acetyl-α-L-rhamnopyranosyl)-L-tyrosine benzyl ester (239806-33-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: zinc; 1,2-dibromoethane; TMSCl / tetrahydrofuran / 2 h / 35 °C

1.2: 83 percent / bis(tri-o-tolylphosphine)palladium dichloride / N,N-dimethyl-acetamide; tetrahydrofuran / 3 h / 20 - 50 °C

2.1: 58 percent / N-methylmorpholine N-oxide / OsO₄ / 2-methyl-propan-2-ol; acetone; H₂O / 24 h / 20 °C

With chloro-trimethyl-silane; 4-methylmorpholine N-oxide; ethylene dibromide; zinc; osmium(VIII) oxide; In tetrahydrofuran; water; acetone; tert-butyl alcohol; 1.1: Metallation / 1.2: Alkylation / 2.1: Oxidation;

DOI:10.1021/jo990253e

upstream raw materials:

N^α-(tert-butoxycarbonyl)-C-(4-O-acetyl-2,3,6-trideoxy-α-L-erythro-hex-2-enopyranosyl)-L-tyrosine benzyl ester

1-bromomethyl-4-iodobenzene

4'-(5-O-acetyl-2,6-anhydro-1,3,4,7-tetradeoxy-α-L-erythro-hept-3-enitol-1-yl)iodobenzene

3,4-di-O-acetyl-6-deoxy-L-glucal

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