(6R,12S)-1-aza-3-(pyroglutamylamino)-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene

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Chemical Name:(6R,12S)-1-aza-3-(pyroglutamylamino)-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene
CAS No.:325460-69-3
Molecular Formula:C₂₀H₂₃N₃O₄
Molecular Weight:369.42
Hs Code.:

Synonyms:(6R,12S)-1-aza-3-(pyroglutamylamino)-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene

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Chemical Property of (6R,12S)-1-aza-3-(pyroglutamylamino)-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene

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Technology Process of (6R,12S)-1-aza-3-(pyroglutamylamino)-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene

There total 12 articles about (6R,12S)-1-aza-3-(pyroglutamylamino)-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene 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: 86.0%

: 325460-76-2
(6R,12S)-1-aza-3-(pyroglutamylamino)-6-[(tert-butyldimethylsiloxy)methyl]-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene

: 325460-69-3
(6R,12S)-1-aza-3-(pyroglutamylamino)-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene

Guidance literature:: With sulfuric acid; In tetrahydrofuran;
DOI:10.1016/S0040-4020(00)00886-3

Reference yield:

: 157662-41-4
(R)-(-)-N-(benzyloxycarbonyl)-2-(2'-oxoethyl)proline methyl ester

: 325460-69-3
(6R,12S)-1-aza-3-(pyroglutamylamino)-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene

Guidance literature:: Multi-step reaction with 10 steps

1.1: 9.96 g / CH₂Cl₂ / -78 - 20 °C

2.1: 61 percent / BF₃*Et₂O / diethyl ether; tetrahydrofuran / -78 - -20 °C

3.1: H₂ / Pd/BaSO₄ / methanol

4.1: 2.4 g / Et₃N / toluene / 21 h / Heating

5.1: 93 percent / LiBH₄ / tetrahydrofuran / 0 - 20 °C

6.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

7.1: KHMDS / toluene; CH₂Cl₂ / 1 h / -78 °C

7.2: 72 percent / O₂ / CH₂Cl₂; toluene / 0.02 h / -78 °C

8.1: 69 percent / NH₃ / methanol / 144 h / 50 °C

9.1: 0.196 g / tetrahydrofuran / -20 - 20 °C

10.1: 86 percent / aq. H₂SO₄ / tetrahydrofuran

With 2,6-dimethylpyridine; lithium borohydride; sulfuric acid; boron trifluoride diethyl etherate; ammonia; hydrogen; potassium hexamethylsilazane; triethylamine; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 1.1: Wittig reaction / 2.1: Addition / 3.1: Hydrogenolysis / 4.1: cyclocondensation / 5.1: Reduction / 6.1: Condensation / 7.1: deprotonation / 7.2: Oxidation / 8.1: Substitution / 9.1: Condensation / 10.1: Hydrolysis;
DOI:10.1016/S0040-4020(00)00886-3

Reference yield:

: 325460-62-6
(2R)-N-(benzyloxycarbonyl)-2-[(E)-3'-(carbomethoxy)prop-2'-enyl]proline methyl ester

: 325460-69-3
(6R,12S)-1-aza-3-(pyroglutamylamino)-6-hydroxymethyl-4-phenyl-2-oxobicyclo[4.3.0]non-3-ene

Guidance literature:: Multi-step reaction with 9 steps

1.1: 61 percent / BF₃*Et₂O / diethyl ether; tetrahydrofuran / -78 - -20 °C

2.1: H₂ / Pd/BaSO₄ / methanol

3.1: 2.4 g / Et₃N / toluene / 21 h / Heating

4.1: 93 percent / LiBH₄ / tetrahydrofuran / 0 - 20 °C

5.1: 96 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

6.1: KHMDS / toluene; CH₂Cl₂ / 1 h / -78 °C

6.2: 72 percent / O₂ / CH₂Cl₂; toluene / 0.02 h / -78 °C

7.1: 69 percent / NH₃ / methanol / 144 h / 50 °C

8.1: 0.196 g / tetrahydrofuran / -20 - 20 °C

9.1: 86 percent / aq. H₂SO₄ / tetrahydrofuran

With 2,6-dimethylpyridine; lithium borohydride; sulfuric acid; boron trifluoride diethyl etherate; ammonia; hydrogen; potassium hexamethylsilazane; triethylamine; Pd-BaSO₄; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; toluene; 1.1: Addition / 2.1: Hydrogenolysis / 3.1: cyclocondensation / 4.1: Reduction / 5.1: Condensation / 6.1: deprotonation / 6.2: Oxidation / 7.1: Substitution / 8.1: Condensation / 9.1: Hydrolysis;
DOI:10.1016/S0040-4020(00)00886-3