(1R,2S)-Methyl hydrogen cis-1,2-cyclohexanediacetate

Base Information

• Chemical Name: (1R,2S)-Methyl hydrogen cis-1,2-cyclohexanediacetate
• CAS No.: 144301-38-2
• Molecular Formula: C₁₁H₁₈O₄
• Molecular Weight: 214.262
• Mol file: 144301-38-2.mol

Synonyms:(1R,2S)-Methyl hydrogen cis-1,2-cyclohexanediacetate

Chemical Property of (1R,2S)-Methyl hydrogen cis-1,2-cyclohexanediacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S)-Methyl hydrogen cis-1,2-cyclohexanediacetate

There total 1 articles about (1R,2S)-Methyl hydrogen cis-1,2-cyclohexanediacetate 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%

(1R-cis)-4-cyclohexene-1,2-diacetic acid monomethyl ester (112168-18-0) → (1R,2S)-Methyl hydrogen cis-1,2-cyclohexanediacetate (144301-38-2)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; for 5h; under 2844.3 Torr;

DOI:10.1021/jo00077a058

Reference yield: 96.0%

(1R,2S)-Methyl hydrogen cis-1,2-cyclohexanediacetate (144301-38-2) → (1R,2S)-2-(2'-Hydroxyethyl)cyclohexaneacetic acid methyl ester (144236-00-0)

Guidance literature:

With diborane; In tetrahydrofuran;

DOI:10.1021/jo00077a058

Reference yield:

(1R,2S)-Methyl hydrogen cis-1,2-cyclohexanediacetate (144301-38-2) → (2R,4R,5S)-α-Amino-2-<2'-(diethylphosphono)ethyl>cyclohexanepropionic acid (144236-07-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 96 percent / diborane / tetrahydrofuran

2: 80 percent / (dimethylamino)pyridine, triethylamine / dimethylformamide / Ambient temperature

3: 72 percent / DIBAL / toluene / 2 h / -78 °C

4: 68 percent / (NH₄)2CO₃ / aq. ethanol / 18 h / 90 °C

5: 94 percent / pyridine / 0 deg C, 15 min; r.t., 2 h

6: 80 percent / LiBr / dimethylformamide / 45 °C

7: 84 percent / NaH / tetrahydrofuran; dimethylformamide / 1.) r.t., 1.5 h, 2.) r.t., 1 h; 80 deg C, 24 h

8: D-hydantoinase

9: 70 percent / NaNO₂, aq. HCl

With pyridine; hydrogenchloride; dmap; D-hydantoinase; ammonium carbonate; sodium hydride; diisobutylaluminium hydride; triethylamine; lithium bromide; diborane; sodium nitrite; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00077a058

upstream raw materials:

(1R-cis)-4-cyclohexene-1,2-diacetic acid monomethyl ester

Downstream raw materials:

(1R,2S)-2-(2'-Hydroxyethyl)cyclohexaneacetic acid methyl ester

(1R,2S)-2-<2'-<(tert-Butyldimethylsilyl)oxy>ethyl>cyclohexylacetaldehyde

(1R,2S)-2-<2'-<(tert-Butyldimethylsilyl)oxy>ethyl>cyclohexaneacetic acid methyl ester

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