(2R,4R)-3,4-dihydro-2-dimethoxymethyl-4-(R-(-)-α-methoxyphenylacetoxy)-2-methyl-6-nitro-2H-1-benzopyran

Base Information

• Chemical Name: (2R,4R)-3,4-dihydro-2-dimethoxymethyl-4-(R-(-)-α-methoxyphenylacetoxy)-2-methyl-6-nitro-2H-1-benzopyran
• CAS No.: 380912-52-7
• Molecular Formula: C₂₂H₂₅NO₈
• Molecular Weight: 431.442
• Mol file: 380912-52-7.mol

Synonyms:(2R,4R)-3,4-dihydro-2-dimethoxymethyl-4-(R-(-)-α-methoxyphenylacetoxy)-2-methyl-6-nitro-2H-1-benzopyran

Chemical Property of (2R,4R)-3,4-dihydro-2-dimethoxymethyl-4-(R-(-)-α-methoxyphenylacetoxy)-2-methyl-6-nitro-2H-1-benzopyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4R)-3,4-dihydro-2-dimethoxymethyl-4-(R-(-)-α-methoxyphenylacetoxy)-2-methyl-6-nitro-2H-1-benzopyran

There total 1 articles about (2R,4R)-3,4-dihydro-2-dimethoxymethyl-4-(R-(-)-α-methoxyphenylacetoxy)-2-methyl-6-nitro-2H-1-benzopyran 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: 28.0%

(R)-methoxyphenylacetic acid (3966-32-3) + 3,4-dihydro-2-dimethoxymethyl-4-hydroxy-2-methyl-6-nitro-2H-1-benzopyran (146821-83-2) → (2R,4R)-3,4-dihydro-2-dimethoxymethyl-4-(R-(-)-α-methoxyphenylacetoxy)-2-methyl-6-nitro-2H-1-benzopyran (380912-52-7) + (2S,4S)-3,4-dihydro-2-dimethoxymethyl-4-(R-(-)-α-methoxyphenylacetoxy)-2-methyl-6-nitro-2H-1-benzopyran (380912-51-6)

Guidance literature:

With dmap; dicyclohexyl-carbodiimide; In ethyl acetate; at 20 ℃; for 1h;

DOI:10.1021/jm010183f

Reference yield:

(2R,4R)-3,4-dihydro-2-dimethoxymethyl-4-(R-(-)-α-methoxyphenylacetoxy)-2-methyl-6-nitro-2H-1-benzopyran (380912-52-7) → (2R,3S,4R)-N'-benzyl-N''-cyano-N-(3,4-dihydro-2-dimethoxymethyl-3-hydroxy-2-methyl-6-nitro-2H-benzopyran-4-yl)guanidine (335381-51-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 1N aq. LiOH / tetrahydrofuran / 0.5 h / 0 °C

2: i-Pr₂NEt / CH₂Cl₂ / 15 h / 20 °C

3: DBU / toluene / Heating

4: (S,S)-Mn(III)-salen complex; NaOCl; Na₂HPO₄ / CH₂Cl₂ / 0 - 20 °C

5: aq. NH₃ / ethanol / 50 °C

6: 64 percent / Et₃N / dimethylformamide; propan-2-ol / 20 °C

7: propan-2-ol

With lithium hydroxide; ammonium hydroxide; sodium hypochlorite; disodium hydrogenphosphate; (S,S)-Mn(III)-salen; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol; toluene;

DOI:10.1021/jm010183f

Reference yield:

(2R,4R)-3,4-dihydro-2-dimethoxymethyl-4-(R-(-)-α-methoxyphenylacetoxy)-2-methyl-6-nitro-2H-1-benzopyran (380912-52-7) → (2R,3S,4R)-N'-(3-chlorophenyl)-N''-cyano-N-(3,4-dihydro-2-dimethoxymethyl-3-hydroxy-2-methyl-6-nitro-2H-benzopyran-4-yl)guanidine

Guidance literature:

Multi-step reaction with 6 steps

1: 1N aq. LiOH / tetrahydrofuran / 0.5 h / 0 °C

2: i-Pr₂NEt / CH₂Cl₂ / 15 h / 20 °C

3: DBU / toluene / Heating

4: (S,S)-Mn(III)-salen complex; NaOCl; Na₂HPO₄ / CH₂Cl₂ / 0 - 20 °C

5: aq. NH₃ / ethanol / 50 °C

6: EDCI / dimethylformamide / 5 h / 20 °C

With lithium hydroxide; ammonium hydroxide; sodium hypochlorite; disodium hydrogenphosphate; (S,S)-Mn(III)-salen; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jm010183f

upstream raw materials:

(R)-methoxyphenylacetic acid

3,4-dihydro-2-dimethoxymethyl-4-hydroxy-2-methyl-6-nitro-2H-1-benzopyran

Downstream raw materials:

C₂₁H₂₂N₄O₇

(2R,3R,4S)-N'-benzyl-N''-cyano-N-(3,4-dihydro-2-dimethoxymethyl-3-hydroxy-2-methyl-6-nitro-2H-benzopyran-4-yl)guanidine

(2R,3S,4R)-N'-benzyl-N''-cyano-N-(3,4-dihydro-2-dimethoxymethyl-3-hydroxy-2-methyl-6-nitro-2H-benzopyran-4-yl)guanidine