ethyl (3R,4S,5R)-4-(tert-butoxycarbonylamino)-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate

Base Information

• Chemical Name: ethyl (3R,4S,5R)-4-(tert-butoxycarbonylamino)-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate
• CAS No.: 1401454-88-3
• Molecular Formula: C₂₀H₃₅NO₈S
• Molecular Weight: 449.566
• Mol file: 1401454-88-3.mol

Synonyms:ethyl (3R,4S,5R)-4-(tert-butoxycarbonylamino)-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate

Chemical Property of ethyl (3R,4S,5R)-4-(tert-butoxycarbonylamino)-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl (3R,4S,5R)-4-(tert-butoxycarbonylamino)-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate

There total 17 articles about ethyl (3R,4S,5R)-4-(tert-butoxycarbonylamino)-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate 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: 95.0%

2-pentanol (584-02-1) + ethyl (1S,5R,6S)-7-(tert-butoxycarbonyl)-5-(methanesulfonyloxy)-7-azabicyclo[4.1.0]hept-2-ene-3-carboxylate (1401454-87-2) → ethyl (3R,4S,5R)-4-(tert-butoxycarbonylamino)-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate (1401454-88-3)

Guidance literature:

With boron trifluoride diethyl etherate; at -10 ℃; for 2h; Inert atmosphere;

DOI:10.1016/j.tet.2015.02.081

Reference yield:

tert-butyl (2S,3S)-2-ethenyl-3-{(1R)-3-(ethoxycarbonyl)-1-[(methylsulfonyl)oxy]but-3-en-1-yl}aziridine-1-carboxylate (1401454-86-1) → ethyl (3R,4S,5R)-4-(tert-butoxycarbonylamino)-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate (1401454-88-3)

Guidance literature:

Multi-step reaction with 2 steps

1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 16 h / 40 °C / Inert atmosphere

2: boron trifluoride diethyl etherate / 2 h / -10 °C / Inert atmosphere

With Hoveyda-Grubbs catalyst second generation; boron trifluoride diethyl etherate; In dichloromethane;

DOI:10.1016/j.tet.2015.02.081

Reference yield:

C16H27NO8S (1401454-84-9) → ethyl (3R,4S,5R)-4-(tert-butoxycarbonylamino)-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-ene-1-carboxylate (1401454-88-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C

2.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.5 h / -20 °C

2.2: 3 h / -20 °C

3.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 18 h / 20 - 40 °C

4.1: boron trifluoride diethyl etherate / 1 h / -8 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; boron trifluoride diethyl etherate; potassium hexamethylsilazane; Dess-Martin periodane; In tetrahydrofuran; dichloromethane; toluene; 2.1: |Wittig Olefination;

DOI:10.1021/jo3015853

upstream raw materials:

(2R,3S)-1-tert-butyl 2-((tert-butyldimethylsilyloxy)methyl)-3-((R)-3-(ethoxycarbonyl)-1-(methanesulfonyloxy)but-3-en-1-yl)-aziridine-1-carboxylate

C₁₆H₂₇NO₈S

(2S,3R)-tert-butyl 2-((R)-3-(ethoxycarbonyl)-1-(methanesulfonyloxy)but-3-en-1-yl)-3-formylaziridine-1-carboxylate

tert-butyl (2S,3S)-2-ethenyl-3-{(1R)-3-(ethoxycarbonyl)-1-[(methylsulfonyl)oxy]but-3-en-1-yl}aziridine-1-carboxylate

Downstream raw materials:

(3R,4S,5R)-4-acetylamino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester

ethyl (3R,4R,5R)-4-acetylamino-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

oseltamivir phosphate

(3R,4S,5R)-4-amino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester