(3aR,3bS,6bR,10aR,10bS)-2,2,9,9-tetramethyl-1,3,8,10-tetraoxacyclohexa[e]cyclopenta[g]-5,6-dione-4-cyclohexylazaindolizidine

Base Information

• Chemical Name: (3aR,3bS,6bR,10aR,10bS)-2,2,9,9-tetramethyl-1,3,8,10-tetraoxacyclohexa[e]cyclopenta[g]-5,6-dione-4-cyclohexylazaindolizidine
• CAS No.: 872038-13-6
• Molecular Formula: C₂₀H₃₀N₂O₆
• Molecular Weight: 394.468
• Mol file: 872038-13-6.mol

Synonyms:(3aR,3bS,6bR,10aR,10bS)-2,2,9,9-tetramethyl-1,3,8,10-tetraoxacyclohexa[e]cyclopenta[g]-5,6-dione-4-cyclohexylazaindolizidine

Chemical Property of (3aR,3bS,6bR,10aR,10bS)-2,2,9,9-tetramethyl-1,3,8,10-tetraoxacyclohexa[e]cyclopenta[g]-5,6-dione-4-cyclohexylazaindolizidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3aR,3bS,6bR,10aR,10bS)-2,2,9,9-tetramethyl-1,3,8,10-tetraoxacyclohexa[e]cyclopenta[g]-5,6-dione-4-cyclohexylazaindolizidine

There total 8 articles about (3aR,3bS,6bR,10aR,10bS)-2,2,9,9-tetramethyl-1,3,8,10-tetraoxacyclohexa[e]cyclopenta[g]-5,6-dione-4-cyclohexylazaindolizidine 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:

2,2-Dimethyl-propionic acid (4R,5S)-5-((1R,2R)-2-azido-1,3-dihydroxy-propyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (872038-08-9) → (3aR,3bS,6bR,10aR,10bS)-2,2,9,9-tetramethyl-1,3,8,10-tetraoxacyclohexa[e]cyclopenta[g]-5,6-dione-4-cyclohexylazaindolizidine (872038-13-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 97 percent / p-toluenesulfonic acid / CH₂Cl₂ / 0.25 h / 20 °C

2: 98 percent / lithium aluminum hydride / diethyl ether / 1 h / 20 °C

3: 93 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate / dimethylformamide / 1 h / 20 °C

4: Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

5: 13 mg / molecular sieves 4 Angstroem; N,N-diisopropylethylamine / CH₂Cl₂ / 17 h / 60 °C

With lithium aluminium tetrahydride; 4 A molecular sieve; Dess-Martin periodane; toluene-4-sulfonic acid; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo0516382

Reference yield:

(2R,3R,4R,5R)-2-azido-1,3:4,5-di(isopropylidenedioxy)-6-pivaloyloxyhexane (872037-91-7) → (3aR,3bS,6bR,10aR,10bS)-2,2,9,9-tetramethyl-1,3,8,10-tetraoxacyclohexa[e]cyclopenta[g]-5,6-dione-4-cyclohexylazaindolizidine (872038-13-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / lithium aluminum hydride / diethyl ether / 1 h / 20 °C

2: 93 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate / dimethylformamide / 1 h / 20 °C

3: Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

4: 13 mg / molecular sieves 4 Angstroem; N,N-diisopropylethylamine / CH₂Cl₂ / 17 h / 60 °C

With lithium aluminium tetrahydride; 4 A molecular sieve; Dess-Martin periodane; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo0516382

Reference yield:

(2R,3R,4R,5R)-5-azido-6-tert-butyldimethylsilanyloxy-2,3-isopropylidenedioxy-1,4-hexanediol (872037-89-3) → (3aR,3bS,6bR,10aR,10bS)-2,2,9,9-tetramethyl-1,3,8,10-tetraoxacyclohexa[e]cyclopenta[g]-5,6-dione-4-cyclohexylazaindolizidine (872038-13-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 79 percent / pyridine / CH₂Cl₂ / 20 h / 20 °C

2: 97 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 1 h / -20 °C

3: 97 percent / p-toluenesulfonic acid / CH₂Cl₂ / 0.25 h / 20 °C

4: 98 percent / lithium aluminum hydride / diethyl ether / 1 h / 20 °C

5: 93 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride; 1-hydroxybenzotriazole hydrate / dimethylformamide / 1 h / 20 °C

6: Dess-Martin periodinane / CH₂Cl₂ / 4 h / 20 °C

7: 13 mg / molecular sieves 4 Angstroem; N,N-diisopropylethylamine / CH₂Cl₂ / 17 h / 60 °C

With pyridine; lithium aluminium tetrahydride; 4 A molecular sieve; tetrabutyl ammonium fluoride; Dess-Martin periodane; toluene-4-sulfonic acid; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo0516382

upstream raw materials:

2,2-Dimethyl-propionic acid (4R,5S)-5-((1R,2R)-2-azido-1,3-dihydroxy-propyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester

(2R,3R,4R,5R)-2-azido-1,3:4,5-di(isopropylidenedioxy)-6-pivaloyloxyhexane

(2R,3R,4R,5R)-5-azido-6-tert-butyldimethylsilanyloxy-2,3-isopropylidenedioxy-1,4-hexanediol

(2R,3R,4R,5R)-2-azido-1-tert-butyldimethylsilanyloxy-4,5-isopropylidenedioxy-6-pivaloyloxy-3-hexanol