(20R,23S)-14,29-Dimethyl-31,33,34,35-tetraethoxy-4-(2,4,6-trinitroanilino)-18,25,32-trioxahexacyclo<25.3.1.1^2,6.1^7,11.1^12,16.1^20,23>pentatriaconta-1(31),2,4,6(35),7,9,11(34),12,14,16(33),27,29-dodecaene

Base Information

• Chemical Name: (20R,23S)-14,29-Dimethyl-31,33,34,35-tetraethoxy-4-(2,4,6-trinitroanilino)-18,25,32-trioxahexacyclo<25.3.1.1^2,6.1^7,11.1^12,16.1^20,23>pentatriaconta-1(31),2,4,6(35),7,9,11(34),12,14,16(33),27,29-dodecaene
• CAS No.: 122110-95-6
• Molecular Formula: C₄₈H₅₂N₄O₁₃
• Molecular Weight: 892.96
• Mol file: 122110-95-6.mol

Synonyms:

Chemical Property of (20R,23S)-14,29-Dimethyl-31,33,34,35-tetraethoxy-4-(2,4,6-trinitroanilino)-18,25,32-trioxahexacyclo<25.3.1.1^2,6.1^7,11.1^12,16.1^20,23>pentatriaconta-1(31),2,4,6(35),7,9,11(34),12,14,16(33),27,29-dodecaene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (20R,23S)-14,29-Dimethyl-31,33,34,35-tetraethoxy-4-(2,4,6-trinitroanilino)-18,25,32-trioxahexacyclo<25.3.1.1^2,6.1^7,11.1^12,16.1^20,23>pentatriaconta-1(31),2,4,6(35),7,9,11(34),12,14,16(33),27,29-dodecaene

There total 11 articles about (20R,23S)-14,29-Dimethyl-31,33,34,35-tetraethoxy-4-(2,4,6-trinitroanilino)-18,25,32-trioxahexacyclo<25.3.1.1^2,6.1^7,11.1^12,16.1^20,23>pentatriaconta-1(31),2,4,6(35),7,9,11(34),12,14,16(33),27,29-dodecaene 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:

2-bromo-6-(hydroxymethyl)-4-methyl-phenol (43135-49-5) → (20R,23S)-14,29-Dimethyl-31,33,34,35-tetraethoxy-4-(2,4,6-trinitroanilino)-18,25,32-trioxahexacyclo<25.3.1.12,6.17,11.112,16.120,23>pentatriaconta-1(31),2,4,6(35),7,9,11(34),12,14,16(33),27,29-dodecaene (122110-95-6,122383-78-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) NaH / 1.) THF, 0 deg C, 2.) reflux, 18 h

2: 1.) BuLi, trimethyl borate, 2.) 2M aq. Na₂CO₃ / 2.) tetrakis(triphenylphosphine)palladium / 1.) THF, hexane, -78 deg C, 8 min; -78 deg C, 30 min; -78 deg C to 0 deg C, 45 min, 2.) EtOH, benzene, reflux, 8 h

3: 78 percent / 1N aq. NaOH, Fe(CO)5 / benzene / 8 h / 25 °C

4: 92 percent / NaHCO₃ / methanol / 4 h / 25 °C

5: 95 percent / HBr / CHCl₃ / 0.33 h

6: NaH / tetrahydrofuran / 10 h / Heating

With sodium hydroxide; n-butyllithium; iron pentacarbonyl; Trimethyl borate; hydrogen bromide; sodium hydride; sodium hydrogencarbonate; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; chloroform; benzene;

DOI:10.1021/ja00198a053

Reference yield:

2-Bromo-6-(ethoxymethyl)-4-methylethoxybenzene (122110-86-5) → (20R,23S)-14,29-Dimethyl-31,33,34,35-tetraethoxy-4-(2,4,6-trinitroanilino)-18,25,32-trioxahexacyclo<25.3.1.12,6.17,11.112,16.120,23>pentatriaconta-1(31),2,4,6(35),7,9,11(34),12,14,16(33),27,29-dodecaene (122110-95-6,122383-78-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) BuLi, trimethyl borate, 2.) 2M aq. Na₂CO₃ / 2.) tetrakis(triphenylphosphine)palladium / 1.) THF, hexane, -78 deg C, 8 min; -78 deg C, 30 min; -78 deg C to 0 deg C, 45 min, 2.) EtOH, benzene, reflux, 8 h

2: 78 percent / 1N aq. NaOH, Fe(CO)5 / benzene / 8 h / 25 °C

3: 92 percent / NaHCO₃ / methanol / 4 h / 25 °C

4: 95 percent / HBr / CHCl₃ / 0.33 h

5: NaH / tetrahydrofuran / 10 h / Heating

With sodium hydroxide; n-butyllithium; iron pentacarbonyl; Trimethyl borate; hydrogen bromide; sodium hydride; sodium hydrogencarbonate; sodium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; chloroform; benzene;

DOI:10.1021/ja00198a053

Reference yield:

3,3'-Diiodo-2,2'-dimethoxy-1,1'-biphenyl (89827-33-8) → (20R,23S)-14,29-Dimethyl-31,33,34,35-tetraethoxy-4-(2,4,6-trinitroanilino)-18,25,32-trioxahexacyclo<25.3.1.12,6.17,11.112,16.120,23>pentatriaconta-1(31),2,4,6(35),7,9,11(34),12,14,16(33),27,29-dodecaene (122110-95-6,122383-78-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 93 percent / BBr₃ / CH₂Cl₂ / 6 h / 25 °C

2: 70 percent / K₂CO₃ / acetone / 72 h / 25 °C

3: 56 percent / aq. HNO₃ / acetic acid / 1.) 30 min, 2.) 25 deg C, 2 h

4: 92 percent / K₂CO₃ / acetone / 8 h / Heating

5: 1.) BuLi, trimethyl borate, 2.) 2M aq. Na₂CO₃ / 2.) tetrakis(triphenylphosphine)palladium / 1.) THF, hexane, -78 deg C, 8 min; -78 deg C, 30 min; -78 deg C to 0 deg C, 45 min, 2.) EtOH, benzene, reflux, 8 h

6: 78 percent / 1N aq. NaOH, Fe(CO)5 / benzene / 8 h / 25 °C

7: 92 percent / NaHCO₃ / methanol / 4 h / 25 °C

8: 95 percent / HBr / CHCl₃ / 0.33 h

9: NaH / tetrahydrofuran / 10 h / Heating

With sodium hydroxide; n-butyllithium; iron pentacarbonyl; Trimethyl borate; hydrogen bromide; nitric acid; boron tribromide; sodium hydride; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; methanol; dichloromethane; chloroform; acetic acid; acetone; benzene;

DOI:10.1021/ja00198a053

upstream raw materials:

cis-2,5-bis(hydroxymethyl)tetrahydrofuran

3,3'''-Bis(bromomethyl)-5,5'''-dimethyl-2,2',2'',2'''-tetraethoxy-5'-(2,4,6-trinitroanilino)-1,1':3',1'':3'',1'''-quaterphenyl

2-bromo-6-(hydroxymethyl)-4-methyl-phenol

2-Bromo-6-(ethoxymethyl)-4-methylethoxybenzene