(3R,4R,5S)-4,5-bis(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene

Base Information

• Chemical Name: (3R,4R,5S)-4,5-bis(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene
• CAS No.: 891831-20-2
• Molecular Formula: C₂₂H₃₇N₃O₅
• Molecular Weight: 423.553
• Mol file: 891831-20-2.mol

Synonyms:(3R,4R,5S)-4,5-bis(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene

Chemical Property of (3R,4R,5S)-4,5-bis(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5S)-4,5-bis(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene

There total 15 articles about (3R,4R,5S)-4,5-bis(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene 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: 60.0%

(3S,4R,5S)-5-(tert-butoxycarbonylamino)-3,4-(tert-butoxycarbonylimino)-1-cyanocyclohexene (891831-19-9) + 2-pentanol (584-02-1) → (3R,4R,5S)-4,5-bis(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene (891831-20-2)

Guidance literature:

With boron trifluoride diethyl etherate;

DOI:10.1016/j.bmcl.2007.11.079

Reference yield:

(4R,5S)-4,5-bis(tert-butoxycarbonylamino)-1-cyano-3-hydroxycyclohexene → (3R,4R,5S)-4,5-bis(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene (891831-20-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / PPh₃; DEAD / tetrahydrofuran / 1 h / 4 °C

2: 52 percent / BF₃*Et₂O / 1 h / 4 °C

With boron trifluoride diethyl etherate; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1021/ja061696k

Reference yield:

(3aR,8aS)-1,3-dibenzylhexahydro-1H-thiepino-[3,4-d]-imidazol-2(3H)-one → (3R,4R,5S)-4,5-bis(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene (891831-20-2)

Guidance literature:

Multi-step reaction with 12 steps

1.1: Oxone / water; methanol; tetrahydrofuran / 4 h / 30 °C

2.1: potassium hydroxide / tetrachloromethane; tert-butyl alcohol / 0.5 h / 27 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.5 h / 25 °C

3.2: 1 h / 80 °C

4.1: dmap / 3 h / 30 °C

5.1: ammonia; sodium / tetrahydrofuran / 2 h / -78 °C

6.1: sodium dihydrogenphosphate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6.5 h / 0 - 20 °C

7.1: diphenyl diselenide; sodium tetrahydroborate / methanol / 2 h / 20 °C

7.2: 1 h

8.1: sodium hydrogencarbonate; Dess-Martin periodane / dichloromethane / 0 - 20 °C

9.1: bis(1,5-cyclooctadiene)nickel ⁽⁰⁾ / tetrahydrofuran

9.2: 0.67 h / 4 °C

9.3: 65.33 h / 4 - 60 °C

10.1: lithium tri-t-butoxyaluminum hydride / tetrahydrofuran / 0.5 h / 4 °C

11.1: triphenylphosphine; diethylazodicarboxylate / tetrahydrofuran; toluene / 1 h / 4 °C

12.1: boron trifluoride diethyl etherate / 1 h / 4 °C

With dmap; Oxone; bis(1,5-cyclooctadiene)nickel ⁽⁰⁾; sodium tetrahydroborate; sodium dihydrogenphosphate; lithium aluminium tetrahydride; diphenyl diselenide; boron trifluoride diethyl etherate; ammonia; sodium; sodium hydrogencarbonate; Dess-Martin periodane; lithium tri-t-butoxyaluminum hydride; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; potassium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; water; toluene; tert-butyl alcohol;

upstream raw materials:

(3S,4R,5S)-5-(tert-butoxycarbonylamino)-3,4-(tert-butoxycarbonylimino)-1-cyanocyclohexene

2-pentanol

(4R,5S)-4,5-bis(tert-butoxycarbonylamino)cyclohexen-3-one

Downstream raw materials:

(3R,4R,5S)-4-amino-5-(tert-butoxycarbonylamino)-1-cyano-3-(1-ethylpropoxy)cyclohexene

(3R,4R,5S)-ethyl 4,5-diamino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

oseltamivir phosphate

oseltamivir