(2R,4R,5S)-α-Amino-2-<2'-(diethylphosphono)ethyl>cyclohexanepropionic acid

Base Information

• Chemical Name: (2R,4R,5S)-α-Amino-2-<2'-(diethylphosphono)ethyl>cyclohexanepropionic acid
• CAS No.: 144236-07-7
• Molecular Formula: C₁₅H₃₀NO₅P
• Molecular Weight: 335.381
• Mol file: 144236-07-7.mol

Synonyms:(2R,4R,5S)-α-Amino-2-<2'-(diethylphosphono)ethyl>cyclohexanepropionic acid

Chemical Property of (2R,4R,5S)-α-Amino-2-<2'-(diethylphosphono)ethyl>cyclohexanepropionic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R,5S)-α-Amino-2-<2'-(diethylphosphono)ethyl>cyclohexanepropionic acid

There total 24 articles about (2R,4R,5S)-α-Amino-2-<2'-(diethylphosphono)ethyl>cyclohexanepropionic acid 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: 70.0%

(2R,4R,5S)-α-<(Aminocarbonyl)amino>-2-<2'-(diethylphosphono)ethyl>cyclohexanepropionic acid (144236-40-8) → (2R,4R,5S)-α-Amino-2-<2'-(diethylphosphono)ethyl>cyclohexanepropionic acid (144236-07-7)

Guidance literature:

With hydrogenchloride; sodium nitrite;

DOI:10.1021/jo00077a058

Reference yield:

(1R,6S)-6-methoxycarbonyl-3-cyclohexene-1-carboxylic acid (31139-02-3,31139-03-4,56124-48-2,88335-93-7,88335-94-8,93603-11-3) → (2R,4R,5S)-α-Amino-2-<2'-(diethylphosphono)ethyl>cyclohexanepropionic acid (144236-07-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 78 percent / LiEt₃BH / tetrahydrofuran / Ambient temperature

2: DIBAL / toluene / 1 h / -45 - -35 °C

3: NaH / tetrahydrofuran; toluene / 1.) r.t., 1 h, 2.) 0 deg C, 30 min; 60 deg C, 4 h

4: 88 percent / pyridine-SO₃, Et₃N / dimethylsulfoxide / 4 h / Ambient temperature

5: 70 percent / LiOH*H₂O / aq. ethanol / 0 deg C, 1 h; r.t., 2 h

6: 95 percent / H₂ / Raney nickel / methanol / 48 h / 65 °C / 25857.4 Torr

7: D-hydantoinase

8: 70 percent / NaNO₂, aq. HCl

With hydrogenchloride; lithium hydroxide; D-hydantoinase; hydrogen; sulfur trioxide pyridine complex; sodium hydride; diisobutylaluminium hydride; lithium triethylborohydride; triethylamine; sodium nitrite; nickel; In tetrahydrofuran; methanol; ethanol; dimethyl sulfoxide; toluene;

DOI:10.1021/jo00077a058

Reference yield:

(3aS,7aR)-3a,4,7,7a-tetrahydroisobenzofuran-1(3H)-one (88586-06-5) → (2R,4R,5S)-α-Amino-2-<2'-(diethylphosphono)ethyl>cyclohexanepropionic acid (144236-07-7)

Guidance literature:

Multi-step reaction with 7 steps

1: DIBAL / toluene / 1 h / -45 - -35 °C

2: NaH / tetrahydrofuran; toluene / 1.) r.t., 1 h, 2.) 0 deg C, 30 min; 60 deg C, 4 h

3: 88 percent / pyridine-SO₃, Et₃N / dimethylsulfoxide / 4 h / Ambient temperature

4: 70 percent / LiOH*H₂O / aq. ethanol / 0 deg C, 1 h; r.t., 2 h

5: 95 percent / H₂ / Raney nickel / methanol / 48 h / 65 °C / 25857.4 Torr

6: D-hydantoinase

7: 70 percent / NaNO₂, aq. HCl

With hydrogenchloride; lithium hydroxide; D-hydantoinase; hydrogen; sulfur trioxide pyridine complex; sodium hydride; diisobutylaluminium hydride; triethylamine; sodium nitrite; nickel; In tetrahydrofuran; methanol; ethanol; dimethyl sulfoxide; toluene;

DOI:10.1021/jo00077a058

upstream raw materials:

(2R,4R,5S)-α-<(Aminocarbonyl)amino>-2-<2'-(diethylphosphono)ethyl>cyclohexanepropionic acid

(3aS,7aR)-3a,4,7,7a-tetrahydroisobenzofuran-1(3H)-one

(1S,6R)-8-oxabicyclo[4.3.0]nonan-7-one

(1S,6R,7RS)-7-hydroxy-8-oxabicyclo[4.3.0]nonane

Downstream raw materials:

NPC 17742

Refernces