C₂₀H₃₁NO₄

Base Information

• Chemical Name: C₂₀H₃₁NO₄
• CAS No.: 1312441-89-6
• Molecular Formula: C₂₀H₃₁NO₄
• Molecular Weight: 349.47
• Mol file: 1312441-89-6.mol

Synonyms:C₂₀H₃₁NO₄

Chemical Property of C₂₀H₃₁NO₄

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₂₀H₃₁NO₄

There total 1 articles about C₂₀H₃₁NO₄ 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: 97.0%

(2R)-4-iodo-1,2-O-isopropylidenebutane-1,2-diol (165657-74-9) + (1R,2R)-(-)-pseudoephedrinepropionamide (192060-67-6) → C20H31NO4 (1312441-89-6)

Guidance literature:

(1R,2R)-(-)-pseudoephedrinepropionamide; With lithium chloride; lithium diisopropyl amide; In tetrahydrofuran; at -78 - 25 ℃; for 1.33333h;

(2R)-4-iodo-1,2-O-isopropylidenebutane-1,2-diol; In tetrahydrofuran; at 0 - 25 ℃; for 3h;

DOI:10.1021/ol201426c

Reference yield:

C20H31NO4 (1312441-89-6) → C44H66O8S2 (1312441-95-4)

Guidance literature:

Multi-step reaction with 10 steps

1.1: tetrahydrofuran; diethyl ether / -78 - 0 °C

2.1: triethylamine; (-)-diisopinocamphenylborane chloride / diethyl ether / 1 h / 0 °C

2.2: 18 h / -78 - -20 °C

3.1: tetramethylammonium triacetoxyborohydride / acetic acid; acetonitrile / 4 h / -20 - 25 °C

4.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h / 0 - 25 °C

5.1: diisobutylaluminium hydride / toluene / 1 h / -20 °C

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 25 °C

7.1: pyridinium p-toluenesulfonate / methanol; chloroform / 48 h / 25 °C

8.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C

8.2: 6 h / 25 °C

9.1: tert.-butyl lithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; pentane / 0.08 h / -78 °C

9.2: 1 h / -78 °C

10.1: manganese(IV) oxide / dichloromethane / 8 h / 25 °C

With manganese(IV) oxide; tert.-butyl lithium; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; (-)-diisopinocamphenylborane chloride; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane; chloroform; acetic acid; toluene; acetonitrile; mineral oil; pentane; 2.2: Aldol condensation;

DOI:10.1021/ol201426c

Reference yield:

C20H31NO4 (1312441-89-6) → 2-[(2R,6S)-6-((2R,4R,5S)-7-{(2S,6S)-6-[3-(2,2-Dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-hydroxy-2-methoxymethoxy-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester (858346-76-6)

Guidance literature:

Multi-step reaction with 17 steps

1.1: tetrahydrofuran; diethyl ether / -78 - 0 °C

2.1: triethylamine; (-)-diisopinocamphenylborane chloride / diethyl ether / 1 h / 0 °C

2.2: 18 h / -78 - -20 °C

3.1: tetramethylammonium triacetoxyborohydride / acetic acid; acetonitrile / 4 h / -20 - 25 °C

4.1: pyridinium p-toluenesulfonate / dichloromethane / 2 h / 0 - 25 °C

5.1: diisobutylaluminium hydride / toluene / 1 h / -20 °C

6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 25 °C

7.1: pyridinium p-toluenesulfonate / methanol; chloroform / 48 h / 25 °C

8.1: sodium hydride / tetrahydrofuran; mineral oil / 0.33 h / 0 °C

8.2: 6 h / 25 °C

9.1: tert.-butyl lithium / tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; pentane / 0.08 h / -78 °C

9.2: 1 h / -78 °C

10.1: manganese(IV) oxide / dichloromethane / 8 h / 25 °C

11.1: 4-toluenesulfonyl azide; potassium carbonate / acetonitrile / 2 h / 25 °C

11.2: 18 h / 25 °C

12.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.5 h / -78 °C

12.2: 0.5 h / -78 - 25 °C

12.3: 3 h / Reflux

13.1: hydrogen / ethanol / 40 h / 50 °C

14.1: pyridine; Dess-Martin periodane / dichloromethane / 5 h / 25 °C

15.1: sodium chlorite; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene / water; tert-butyl alcohol / 4 h / 25 °C

16.1: caesium carbonate / acetonitrile / 2 h / 25 °C

17.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / 25 °C

With pyridine; manganese(IV) oxide; sodium chlorite; 4-toluenesulfonyl azide; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; hydrogen; tert.-butyl lithium; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; sodium hydride; diisobutylaluminium hydride; potassium carbonate; caesium carbonate; Dess-Martin periodane; triethylamine; N-ethyl-N,N-diisopropylamine; (-)-diisopinocamphenylborane chloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; ethanol; dichloromethane; chloroform; water; acetic acid; toluene; acetonitrile; mineral oil; tert-butyl alcohol; pentane; 2.2: Aldol condensation / 12.3: Suzuki coupling / 14.1: Dess-Martin oxidation;

DOI:10.1021/ol201426c

upstream raw materials:

(2R)-4-iodo-1,2-O-isopropylidenebutane-1,2-diol

(1R,2R)-(-)-pseudoephedrinepropionamide

Downstream raw materials:

2-[(2R,6S)-6-((2R,4R,5S)-7-{(2S,6S)-6-[3-(2,2-Dimethyl-4-oxo-4H-benzo[1,3]dioxin-5-yl)-propyl]-tetrahydro-pyran-2-yl}-4-hydroxy-2-methoxymethoxy-5-methyl-heptyl)-tetrahydro-pyran-2-yl]-2-methyl-propionic acid benzyl ester

C₂₉H₄₆O₆

C₂₉H₄₈O₆

C₃₇H₅₄O₇