tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-hydroxycyclohex-3-en-1-yl]carbamate

Base Information

• Chemical Name: tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-hydroxycyclohex-3-en-1-yl]carbamate
• CAS No.: 927395-71-9
• Molecular Formula: C₁₄H₂₁N₃O₄
• Molecular Weight: 295.338
• Mol file: 927395-71-9.mol

Synonyms:tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-hydroxycyclohex-3-en-1-yl]carbamate

Chemical Property of tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-hydroxycyclohex-3-en-1-yl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-hydroxycyclohex-3-en-1-yl]carbamate

There total 13 articles about tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-hydroxycyclohex-3-en-1-yl]carbamate 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: 80.0%

tert-butyl [(1S,5S,6R)-6-acetylamino-3-cyano-5-hydroxycyclohex-3-en-1-yl]carbamate (927395-70-8) → tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-hydroxycyclohex-3-en-1-yl]carbamate (927395-71-9)

Guidance literature:

tert-butyl [(1S,5S,6R)-6-acetylamino-3-cyano-5-hydroxycyclohex-3-en-1-yl]carbamate; With triphenylphosphine; diethylazodicarboxylate; 4-nitro-benzoic acid; In tetrahydrofuran; toluene; at 4 ℃; for 0.25h;

With lithium hydroxide; In tetrahydrofuran; water; toluene; at -20 ℃; for 2.5h;

DOI:10.1021/ol062663c

Reference yield:

7-(3,5-dinitrobenzoyl)-7-azabicyclo[4.1.0]hept-3-ene → tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-hydroxycyclohex-3-en-1-yl]carbamate (927395-71-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: Y(O-i-Pr)3; TMSN₃; 2,6-dimethylphenol / 6-deoxy-6-(diphenylphosphoryl)-arabino-hexitol-based ligand / various solvent(s) / 12 h / 20 °C

2.1: 4-(dimethylamino)pyridine / acetonitrile / 1 h / 20 °C

2.2: 98 percent / NaOH / acetonitrile; H₂O / 1 h / 20 °C

3.1: potassium carbonate; iodine; potassium iodide / CHCl₃ / 14 h / 60 °C

3.2: 85 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CHCl₃ / 4 h / 4 - 20 °C

4.1: 99 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 4 - 20 °C

5.1: 83 percent / 2,6-lutidine / CHCl₃ / 19 h / 60 °C

6.1: 86 percent / cesium carbonate / butan-1-ol / 16 h / 4 - 20 °C

7.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 - 20 °C

8.1: lithium cyanide / tetrahydrofuran / 4 h / -20 °C

9.1: toluene / 0.67 h / 140 °C

9.2: 23 percent / NaOH / H₂O; toluene / 1 h / 20 °C

10.1: triphenylphosphine; DEAD; p-nitrobenzoic acid / tetrahydrofuran; toluene / 0.25 h / 4 °C

10.2: 80 percent / lithium hydroxide / tetrahydrofuran; toluene; H₂O / 2.5 h / -20 °C

With 2,6-dimethylpyridine; dmap; 2.6-dimethylphenol; yttrium(III) isopropoxide; trimethylsilylazide; lithium cyanide; iodine; potassium carbonate; caesium carbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; potassium iodide; diethylazodicarboxylate; 4-nitro-benzoic acid; 6-deoxy-6-(diphenylphosphoryl)-arabino-hexitol-based ligand; In tetrahydrofuran; dichloromethane; chloroform; toluene; acetonitrile; butan-1-ol; 10.1: Mitsunobu reaction;

DOI:10.1021/ol062663c

Reference yield:

(4S,5S)-4-azido-5-(tert-butoxycarbonylamino)cyclohexene (891831-14-4) → tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-hydroxycyclohex-3-en-1-yl]carbamate (927395-71-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: potassium carbonate; iodine; potassium iodide / CHCl₃ / 14 h / 60 °C

1.2: 85 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CHCl₃ / 4 h / 4 - 20 °C

2.1: 99 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 4 - 20 °C

3.1: 83 percent / 2,6-lutidine / CHCl₃ / 19 h / 60 °C

4.1: 86 percent / cesium carbonate / butan-1-ol / 16 h / 4 - 20 °C

5.1: 90 percent / Dess-Martin periodinane / CH₂Cl₂ / 4 - 20 °C

6.1: lithium cyanide / tetrahydrofuran / 4 h / -20 °C

7.1: toluene / 0.67 h / 140 °C

7.2: 23 percent / NaOH / H₂O; toluene / 1 h / 20 °C

8.1: triphenylphosphine; DEAD; p-nitrobenzoic acid / tetrahydrofuran; toluene / 0.25 h / 4 °C

8.2: 80 percent / lithium hydroxide / tetrahydrofuran; toluene; H₂O / 2.5 h / -20 °C

With 2,6-dimethylpyridine; dmap; lithium cyanide; iodine; potassium carbonate; caesium carbonate; Dess-Martin periodane; triethylamine; triphenylphosphine; potassium iodide; diethylazodicarboxylate; 4-nitro-benzoic acid; In tetrahydrofuran; dichloromethane; chloroform; toluene; butan-1-ol; 8.1: Mitsunobu reaction;

DOI:10.1021/ol062663c

upstream raw materials:

tert-butyl [(1S,5S,6R)-6-acetylamino-3-cyano-5-hydroxycyclohex-3-en-1-yl]carbamate

(6-acetylamino-3-cyano-5-oxo-cyclohex-3-enyl)-carbamic acid tert-butyl ester

(4S,5S)-4-azido-5-(tert-butoxycarbonylamino)cyclohexene

(4S,5S)-4-azido-5-(3,5-dinitrobenzoylamino)cyclohexene

Downstream raw materials:

oseltamivir phosphate

tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-(1-ethylpropoxy)cyclohex-3-en-1-yl]carbamate

Refernces

• 1、 Yamatsugu, Kenzo,Kamijo, Shin,Suto, Yutaka,Kanai, Motomu,Shibasaki, Masakatsu. "A concise synthesis of Tamiflu: third generation route via the Diels-Alder reaction and the Curtius rearrangement". . p. 1403 - 1406. Retrieved 2007/10/03.