{1R-[4-cyano-6S-(1R-methylcarbamoyl-2-naphthalen-2-yl-ethylcarbamoyl)-tetrahydro-pyran-2R-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

Base Information

Chemical Name:{1R-[4-cyano-6S-(1R-methylcarbamoyl-2-naphthalen-2-yl-ethylcarbamoyl)-tetrahydro-pyran-2R-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester
CAS No.:623143-69-1
Molecular Formula:C₃₄H₄₀N₄O₅
Molecular Weight:584.715
Hs Code.:

Synonyms:{1R-[4-cyano-6S-(1R-methylcarbamoyl-2-naphthalen-2-yl-ethylcarbamoyl)-tetrahydro-pyran-2R-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

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Chemical Property of {1R-[4-cyano-6S-(1R-methylcarbamoyl-2-naphthalen-2-yl-ethylcarbamoyl)-tetrahydro-pyran-2R-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

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Technology Process of {1R-[4-cyano-6S-(1R-methylcarbamoyl-2-naphthalen-2-yl-ethylcarbamoyl)-tetrahydro-pyran-2R-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

There total 10 articles about {1R-[4-cyano-6S-(1R-methylcarbamoyl-2-naphthalen-2-yl-ethylcarbamoyl)-tetrahydro-pyran-2R-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl 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:

: (2S,6R)-6-((R)-1-tert-Butoxycarbonylamino-2-phenyl-ethyl)-4-cyano-tetrahydro-pyran-2-carboxylic acid

: 2-amino-N-methyl-3-naphthalen-2-yl-propionamide; compound with trifluoro-acetic acid

: 623143-69-1
{1R-[4-cyano-6S-(1R-methylcarbamoyl-2-naphthalen-2-yl-ethylcarbamoyl)-tetrahydro-pyran-2R-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

Guidance literature:: With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20 ℃;
DOI:10.1016/S0968-0896(03)00274-8

Reference yield:

: 77119-85-8
N-(tert-butoxycarbonyl)-D-phenylalaninal

: 623143-69-1
{1R-[4-cyano-6S-(1R-methylcarbamoyl-2-naphthalen-2-yl-ethylcarbamoyl)-tetrahydro-pyran-2R-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 steps

1: LiClO₄ / diethyl ether / 20 °C

2: 79 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / 0 °C

3: p-TsOH / 12 h / 80 °C

4: aq. KOH / ethanol / 1 h / Heating

5: aq. AcOH / tetrahydrofuran / 12 h / 60 °C

6: methanol / 20 °C

7: 90 percent / NaCN / dimethylformamide / 2 h / 20 °C

8: 69 percent / t-BuOH; SmI₂ / tetrahydrofuran / 4 h / 20 °C

9: aq. LiOH / tetrahydrofuran / 2 h / 20 °C

10: 0.14 g / HOBt; NMM; EDCI / dimethylformamide / 20 °C

With 4-methyl-morpholine; potassium hydroxide; lithium hydroxide; samarium diiodide; boron trifluoride diethyl etherate; sodium cyanide; lithium perchlorate; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tert-butyl alcohol; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; 1: hetero Diels-Alder cyclization;
DOI:10.1016/S0968-0896(03)00274-8

Reference yield:

: 524018-08-4
[1-(4-oxo-3,4-dihydro-2H-pyran-2-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester

: 623143-69-1
{1R-[4-cyano-6S-(1R-methylcarbamoyl-2-naphthalen-2-yl-ethylcarbamoyl)-tetrahydro-pyran-2R-yl]-2-phenyl-ethyl}-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 79 percent / BF₃*Et₂O / CH₂Cl₂ / 2 h / 0 °C

2: p-TsOH / 12 h / 80 °C

3: aq. KOH / ethanol / 1 h / Heating

4: aq. AcOH / tetrahydrofuran / 12 h / 60 °C

5: methanol / 20 °C

6: 90 percent / NaCN / dimethylformamide / 2 h / 20 °C

7: 69 percent / t-BuOH; SmI₂ / tetrahydrofuran / 4 h / 20 °C

8: aq. LiOH / tetrahydrofuran / 2 h / 20 °C

9: 0.14 g / HOBt; NMM; EDCI / dimethylformamide / 20 °C

With 4-methyl-morpholine; potassium hydroxide; lithium hydroxide; samarium diiodide; boron trifluoride diethyl etherate; sodium cyanide; benzotriazol-1-ol; toluene-4-sulfonic acid; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tert-butyl alcohol; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(03)00274-8