(1R,2S,5S)-2-[(R)-2-Carbamoyloxy-1-(3,5-dimethoxy-2-methoxymethoxy-4-methyl-phenyl)-ethyl]-3,6-diaza-bicyclo[3.1.0]hexane-3,6-dicarboxylic acid dibenzyl ester

Base Information

Chemical Name:(1R,2S,5S)-2-[(R)-2-Carbamoyloxy-1-(3,5-dimethoxy-2-methoxymethoxy-4-methyl-phenyl)-ethyl]-3,6-diaza-bicyclo[3.1.0]hexane-3,6-dicarboxylic acid dibenzyl ester
CAS No.:792923-02-5
Molecular Formula:C₃₄H₃₉N₃O₁₀
Molecular Weight:649.698
Hs Code.:

(1R,2S,5S)-2-[(R)-2-Carbamoyloxy-1-(3,5-dimethoxy-2-methoxymethoxy-4-methyl-phenyl)-ethyl]-3,6-diaza-bicyclo[3.1.0]hexane-3,6-dicarboxylic acid dibenzyl ester

Synonyms:(1R,2S,5S)-2-[(R)-2-Carbamoyloxy-1-(3,5-dimethoxy-2-methoxymethoxy-4-methyl-phenyl)-ethyl]-3,6-diaza-bicyclo[3.1.0]hexane-3,6-dicarboxylic acid dibenzyl ester

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Chemical Property of (1R,2S,5S)-2-[(R)-2-Carbamoyloxy-1-(3,5-dimethoxy-2-methoxymethoxy-4-methyl-phenyl)-ethyl]-3,6-diaza-bicyclo[3.1.0]hexane-3,6-dicarboxylic acid dibenzyl ester

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of (1R,2S,5S)-2-[(R)-2-Carbamoyloxy-1-(3,5-dimethoxy-2-methoxymethoxy-4-methyl-phenyl)-ethyl]-3,6-diaza-bicyclo[3.1.0]hexane-3,6-dicarboxylic acid dibenzyl ester

There total 14 articles about (1R,2S,5S)-2-[(R)-2-Carbamoyloxy-1-(3,5-dimethoxy-2-methoxymethoxy-4-methyl-phenyl)-ethyl]-3,6-diaza-bicyclo[3.1.0]hexane-3,6-dicarboxylic acid dibenzyl 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: 86.0%

: 3019-71-4
Trichloroacetyl isocyanate

: 792923-01-4
(1R,2S,5S)-2-[(R)-1-(3,5-Dimethoxy-2-methoxymethoxy-4-methyl-phenyl)-2-hydroxy-ethyl]-3,6-diaza-bicyclo[3.1.0]hexane-3,6-dicarboxylic acid dibenzyl ester

: 792923-02-5
(1R,2S,5S)-2-[(R)-2-Carbamoyloxy-1-(3,5-dimethoxy-2-methoxymethoxy-4-methyl-phenyl)-ethyl]-3,6-diaza-bicyclo[3.1.0]hexane-3,6-dicarboxylic acid dibenzyl ester

Guidance literature:: In dichloromethane; at 65 ℃; for 36h;
DOI:10.1021/jo048924i

Reference yield:

: 19676-67-6
2,4-dimethoxy-3-methylphenol

: 792923-02-5
(1R,2S,5S)-2-[(R)-2-Carbamoyloxy-1-(3,5-dimethoxy-2-methoxymethoxy-4-methyl-phenyl)-ethyl]-3,6-diaza-bicyclo[3.1.0]hexane-3,6-dicarboxylic acid dibenzyl ester

Guidance literature:: Multi-step reaction with 11 steps

1.1: NaH / tetrahydrofuran; dimethylformamide / 1 h / 25 °C

1.2: 89 percent / tetrahydrofuran; dimethylformamide / 1 h / 25 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C

2.2: 86 percent / tetrahydrofuran; hexane / 0 - 25 °C

3.1: 89 percent / Et₃N; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 3 h / 25 °C

4.1: SmI₂; n-Bu₃SnCl / Pd(PPh₃)4 / tetrahydrofuran / 12 h / 25 °C

4.2: 120 mg / BF₃*OEt₂ / CH₂Cl₂ / 2 h / -40 °C

5.1: SnCl₂; thiophenol; Et₃N / acetonitrile / 2 h / 0 °C

6.1: 933 mg / Et₃N / CH₂Cl₂ / 3 h / 20 °C

7.1: 81 percent / diisopropyl azodicarboxylate; Ph₃P / tetrahydrofuran / 2 h / 20 °C

8.1: O₃ / methanol; CH₂Cl₂ / 0.5 h / -78 °C

8.2: 63 percent / NaBH₄ / methanol; CH₂Cl₂ / 4 h / 0 °C

9.1: TMSOTf; 2,6-di-tert-butylpyridine / CH₂Cl₂ / 2 h / 0 °C

10.1: 56.6 mg / Et₃N / CH₂Cl₂ / 0 - 20 °C

11.1: 86 percent / CH₂Cl₂ / 36 h / 65 °C

With dmap; n-butyllithium; 2,6-di-tert-butyl-pyridine; samarium diiodide; trimethylsilyl trifluoromethanesulfonate; di-isopropyl azodicarboxylate; tributyltin chloride; sodium hydride; ozone; thiophenol; triethylamine; triphenylphosphine; tin(ll) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1021/jo048924i

Reference yield:

: 7149-92-0
2,4-dimethoxy-3-methylbenzaldehyde

: 792923-02-5
(1R,2S,5S)-2-[(R)-2-Carbamoyloxy-1-(3,5-dimethoxy-2-methoxymethoxy-4-methyl-phenyl)-ethyl]-3,6-diaza-bicyclo[3.1.0]hexane-3,6-dicarboxylic acid dibenzyl ester

Guidance literature:: Multi-step reaction with 12 steps

1.1: m-CPBA / CH₂Cl₂ / 3 h / 0 °C

1.2: 87 percent / KOH / methanol / 1 h / 0 °C

2.1: NaH / tetrahydrofuran; dimethylformamide / 1 h / 25 °C

2.2: 89 percent / tetrahydrofuran; dimethylformamide / 1 h / 25 °C

3.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C

3.2: 86 percent / tetrahydrofuran; hexane / 0 - 25 °C

4.1: 89 percent / Et₃N; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 3 h / 25 °C

5.1: SmI₂; n-Bu₃SnCl / Pd(PPh₃)4 / tetrahydrofuran / 12 h / 25 °C

5.2: 120 mg / BF₃*OEt₂ / CH₂Cl₂ / 2 h / -40 °C

6.1: SnCl₂; thiophenol; Et₃N / acetonitrile / 2 h / 0 °C

7.1: 933 mg / Et₃N / CH₂Cl₂ / 3 h / 20 °C

8.1: 81 percent / diisopropyl azodicarboxylate; Ph₃P / tetrahydrofuran / 2 h / 20 °C

9.1: O₃ / methanol; CH₂Cl₂ / 0.5 h / -78 °C

9.2: 63 percent / NaBH₄ / methanol; CH₂Cl₂ / 4 h / 0 °C

10.1: TMSOTf; 2,6-di-tert-butylpyridine / CH₂Cl₂ / 2 h / 0 °C

11.1: 56.6 mg / Et₃N / CH₂Cl₂ / 0 - 20 °C

12.1: 86 percent / CH₂Cl₂ / 36 h / 65 °C

With dmap; n-butyllithium; 2,6-di-tert-butyl-pyridine; samarium diiodide; trimethylsilyl trifluoromethanesulfonate; di-isopropyl azodicarboxylate; tributyltin chloride; sodium hydride; ozone; thiophenol; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; tin(ll) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Baeyer-Villiger oxidation;
DOI:10.1021/jo048924i