(3R,4S,5R)-4-[(diethoxyphosphoryl)amino]-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-enecarboxylic acid ethyl ester

Base Information

• Chemical Name: (3R,4S,5R)-4-[(diethoxyphosphoryl)amino]-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-enecarboxylic acid ethyl ester
• CAS No.: 1132659-97-2
• Molecular Formula: C₁₉H₃₆NO₉PS
• Molecular Weight: 485.536
• Mol file: 1132659-97-2.mol

Synonyms:(3R,4S,5R)-4-[(diethoxyphosphoryl)amino]-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-enecarboxylic acid ethyl ester

Chemical Property of (3R,4S,5R)-4-[(diethoxyphosphoryl)amino]-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-enecarboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S,5R)-4-[(diethoxyphosphoryl)amino]-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-enecarboxylic acid ethyl ester

There total 8 articles about (3R,4S,5R)-4-[(diethoxyphosphoryl)amino]-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-enecarboxylic acid ethyl 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: 46.0%

2-pentanol (584-02-1) + (1S,5R,6S)-7-(diethoxy-phosphoryl)-5-methanesulfonyloxy-7-aza-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid ethyl ester (1132659-96-1) → (3R,4S,5R)-4-[(diethoxyphosphoryl)amino]-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-enecarboxylic acid ethyl ester (1132659-97-2)

Guidance literature:

With boron trifluoride diethyl etherate; at 0 - 20 ℃; Inert atmosphere;

Reference yield:

(3R,4S,5R)-3,4,5-tris-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester (1132659-94-9) → (3R,4S,5R)-4-[(diethoxyphosphoryl)amino]-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-enecarboxylic acid ethyl ester (1132659-97-2)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium azide; ammonium chloride / methanol / 6.5 h / 10 - 20 °C

2: toluene / 1 h / 20 °C

3: toluene / 7 h / Reflux

4: boron trifluoride diethyl etherate / 17 h / 0 - 20 °C

With sodium azide; boron trifluoride diethyl etherate; ammonium chloride; In methanol; toluene;

DOI:10.1007/s11172-013-0024-2

Reference yield:

shikimic acid (138-59-0) → (3R,4S,5R)-4-[(diethoxyphosphoryl)amino]-3-(1-ethylpropoxy)-5-(methanesulfonyloxy)cyclohex-1-enecarboxylic acid ethyl ester (1132659-97-2)

Guidance literature:

Multi-step reaction with 6 steps

1: KU-2-8 cationite / 15 h / Reflux

2: triethylamine / ethyl acetate / 4 h / 0 - 3 °C

3: sodium azide; ammonium chloride / methanol / 6.5 h / 10 - 20 °C

4: toluene / 1 h / 20 °C

5: toluene / 7 h / Reflux

6: boron trifluoride diethyl etherate / 17 h / 0 - 20 °C

With sodium azide; boron trifluoride diethyl etherate; ammonium chloride; triethylamine; In methanol; ethyl acetate; toluene;

DOI:10.1007/s11172-013-0024-2

upstream raw materials:

2-pentanol

(1S,5R,6S)-7-(diethoxy-phosphoryl)-5-methanesulfonyloxy-7-aza-bicyclo[4.1.0]hept-2-ene-3-carboxylic acid ethyl ester

shikimic acid

(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid ethyl ester

Downstream raw materials:

(3R,4R,5S)-5-azido-4-(diethoxy-phosphorylamino)-3-(1-ethyl-propoxy)-cyclohex-1-enecarboxylic acid ethyl ester

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

oseltamivir phosphate

oseltamivir