6R-(1R-tert-butoxycarbonylamino-2-phenyl-ethyl)-4-cyano-tetrahydro-pyran-2S-carboxylic acid methyl ester

Base Information

Chemical Name:6R-(1R-tert-butoxycarbonylamino-2-phenyl-ethyl)-4-cyano-tetrahydro-pyran-2S-carboxylic acid methyl ester
CAS No.:623143-68-0
Molecular Formula:C₂₁H₂₈N₂O₅
Molecular Weight:388.464
Hs Code.:

Synonyms:6R-(1R-tert-butoxycarbonylamino-2-phenyl-ethyl)-4-cyano-tetrahydro-pyran-2S-carboxylic acid methyl ester

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Chemical Property of 6R-(1R-tert-butoxycarbonylamino-2-phenyl-ethyl)-4-cyano-tetrahydro-pyran-2S-carboxylic acid methyl ester

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Technology Process of 6R-(1R-tert-butoxycarbonylamino-2-phenyl-ethyl)-4-cyano-tetrahydro-pyran-2S-carboxylic acid methyl ester

There total 8 articles about 6R-(1R-tert-butoxycarbonylamino-2-phenyl-ethyl)-4-cyano-tetrahydro-pyran-2S-carboxylic acid methyl 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: 69.0%

: 623143-67-9
6R-(1R-tert-butoxycarbonylamino-2-phenyl-ethyl)-4-cyano-4-(diethoxy-phosphoryloxy)-tetrahydro-pyran-2S-carboxylic acid methyl ester

: 623143-68-0
6R-(1R-tert-butoxycarbonylamino-2-phenyl-ethyl)-4-cyano-tetrahydro-pyran-2S-carboxylic acid methyl ester

Guidance literature:: With samarium diiodide; tert-butyl alcohol; In tetrahydrofuran; at 20 ℃; for 4h;
DOI:10.1016/S0968-0896(03)00274-8

Reference yield:

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

: 623143-68-0
6R-(1R-tert-butoxycarbonylamino-2-phenyl-ethyl)-4-cyano-tetrahydro-pyran-2S-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 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

With potassium hydroxide; samarium diiodide; boron trifluoride diethyl etherate; sodium cyanide; lithium perchlorate; toluene-4-sulfonic acid; acetic acid; 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

: 623143-68-0
6R-(1R-tert-butoxycarbonylamino-2-phenyl-ethyl)-4-cyano-tetrahydro-pyran-2S-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 7 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

With potassium hydroxide; samarium diiodide; boron trifluoride diethyl etherate; sodium cyanide; toluene-4-sulfonic acid; acetic acid; tert-butyl alcohol; In tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0968-0896(03)00274-8