(3S,7S,10S,14R)-6,10-Dibenzyl-14-hydroxy-2-oxa-6,9,12-triaza-tricyclo[13.2.2.0^3,7]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-8,11-dione

Base Information

• Chemical Name: (3S,7S,10S,14R)-6,10-Dibenzyl-14-hydroxy-2-oxa-6,9,12-triaza-tricyclo[13.2.2.0^3,7]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-8,11-dione
• CAS No.: 312583-23-6
• Molecular Formula: C₂₉H₃₁N₃O₄
• Molecular Weight: 485.583

Synonyms:(3S,7S,10S,14R)-6,10-Dibenzyl-14-hydroxy-2-oxa-6,9,12-triaza-tricyclo[13.2.2.0^3,7]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-8,11-dione

Chemical Property of (3S,7S,10S,14R)-6,10-Dibenzyl-14-hydroxy-2-oxa-6,9,12-triaza-tricyclo[13.2.2.0^3,7]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-8,11-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of (3S,7S,10S,14R)-6,10-Dibenzyl-14-hydroxy-2-oxa-6,9,12-triaza-tricyclo[13.2.2.0^3,7]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-8,11-dione

There total 8 articles about (3S,7S,10S,14R)-6,10-Dibenzyl-14-hydroxy-2-oxa-6,9,12-triaza-tricyclo[13.2.2.0^3,7]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-8,11-dione 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:

(3S,7S,10S,14R)-18-Amino-6,10-dibenzyl-14-hydroxy-2-oxa-6,9,12-triaza-tricyclo[13.2.2.03,7]nonadeca-1(18),15(19),16-triene-8,11-dione → (3S,7S,10S,14R)-6,10-Dibenzyl-14-hydroxy-2-oxa-6,9,12-triaza-tricyclo[13.2.2.03,7]nonadeca-1(18),15(19),16-triene-8,11-dione (312583-23-6)

Guidance literature:

With copper(I) oxide; hypophosphorous acid; sodium nitrite; tin(ll) chloride; In tetrahydrofuran; at 0 - 20 ℃; for 4h;

DOI:10.1002/chem.200401070

Reference yield:

(2S,3S)-1-Benzyl-3-hydroxy-pyrrolidine-2-carboxylic acid {(S)-1-[(R)-2-(4-fluoro-3-nitro-phenyl)-2-hydroxy-ethylcarbamoyl]-2-phenyl-ethyl}-amide (312583-22-5) → (3S,7S,10S,14R)-6,10-Dibenzyl-14-hydroxy-2-oxa-6,9,12-triaza-tricyclo[13.2.2.03,7]nonadeca-1(18),15(19),16-triene-8,11-dione (312583-23-6)

Guidance literature:

Multistep reaction;

DOI:10.1016/S0040-4039(00)01335-6

Reference yield:

{(S)-1-[(R)-2-(4-Fluoro-3-nitro-phenyl)-2-hydroxy-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester (856165-43-0) → (3S,7S,10S,14R)-6,10-Dibenzyl-14-hydroxy-2-oxa-6,9,12-triaza-tricyclo[13.2.2.03,7]nonadeca-1(18),15(19),16-triene-8,11-dione (312583-23-6)

Guidance literature:

Multi-step reaction with 5 steps

1: aq. HCl / acetonitrile / 1 h / 20 °C

2: 6.75 g / Et₃N; HOBT; EDCI / dimethylformamide / 17 h / 20 °C

3: 415 mg / TBAF; 3 Angstroem molecular sieves / dimethylsulfoxide; tetrahydrofuran / 20 h / 60 °C

4: H₂ / Pd/C / ethyl acetate; methanol / 2.5 h / 20 °C

5: aq. H₃PO₂; NaNO₂; Cu₂O / SnCl₂ / tetrahydrofuran / 4 h / 0 - 20 °C

With copper(I) oxide; hydrogenchloride; 3 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; hypophosphorous acid; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium nitrite; palladium on activated charcoal; tin(ll) chloride; In tetrahydrofuran; methanol; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/chem.200401070

upstream raw materials:

(2S,3S)-1-Benzyl-3-hydroxy-pyrrolidine-2-carboxylic acid {(S)-1-[(R)-2-(4-fluoro-3-nitro-phenyl)-2-hydroxy-ethylcarbamoyl]-2-phenyl-ethyl}-amide

{(S)-1-[(R)-2-(4-Fluoro-3-nitro-phenyl)-2-hydroxy-ethylcarbamoyl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

[(S)-1-((Z)-(3S,7S,10S)-10-Benzyl-8,11-dioxo-2-oxa-6,9,12-triaza-tricyclo[13.2.2.0^3,7]nonadeca-1⁽¹⁸⁾,13,15⁽¹⁹⁾,16-tetraene-6-carbonyl)-2-methyl-propyl]-carbamic acid tert-butyl ester

[(S)-1-((3S,7S,10S,14R)-10-Benzyl-14-hydroxy-8,11-dioxo-2-oxa-6,9,12-triaza-tricyclo[13.2.2.0^3,7]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-6-carbonyl)-2-methyl-propyl]-carbamic acid tert-butyl ester

{(S)-1-[(S)-1-((Z)-(3S,7S,10S)-10-Benzyl-8,11-dioxo-2-oxa-6,9,12-triaza-tricyclo[13.2.2.0^3,7]nonadeca-1⁽¹⁸⁾,13,15⁽¹⁹⁾,16-tetraene-6-carbonyl)-2-methyl-propylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester

[(S)-1-((3S,7S,10S,14S)-10-Benzyl-8,11-dioxo-14-phenylselanyl-2-oxa-6,9,12-triaza-tricyclo[13.2.2.0^3,7]nonadeca-1⁽¹⁸⁾,15⁽¹⁹⁾,16-triene-6-carbonyl)-2-methyl-propyl]-carbamic acid tert-butyl ester

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