(R)-2-Benzyloxy-1-methyl-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethylamine

Base Information

• Chemical Name: (R)-2-Benzyloxy-1-methyl-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethylamine
• CAS No.: 189571-95-7
• Molecular Formula: C₂₁H₃₁NO₆
• Molecular Weight: 393.48

Synonyms:(R)-2-Benzyloxy-1-methyl-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethylamine

Chemical Property of (R)-2-Benzyloxy-1-methyl-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethylamine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-2-Benzyloxy-1-methyl-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethylamine

There total 9 articles about (R)-2-Benzyloxy-1-methyl-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethylamine 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:

(R)-2-Benzyloxymethyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-aziridine (189571-92-4) → (R)-2-Benzyloxy-1-methyl-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethylamine (189571-95-7)

Guidance literature:

With hydrogen; nickel; In ethyl acetate; for 96h; under 90007.2 Torr;

DOI:10.1016/S0040-4020(97)00240-8

Reference yield:

benzyl bromide (100-39-0) → (R)-2-Benzyloxy-1-methyl-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethylamine (189571-95-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 89 percent / bis-tributylstannyl oxide, tetrabutylammonium bromide / benzene / 24 h / Heating

2: 95 percent / oxalyl chloride, DMSO, triethylamine / CH₂Cl₂ / 2 h / Ambient temperature

3: 82 percent / lithium diisopropylamide / tetrahydrofuran; hexane / -78 - 20 °C

4: 93 percent / sodium hydride / tetrahydrofuran / 12 h / Ambient temperature

5: 93 percent / sodium azide, 15-crown-5 / hexamethylphosphoric acid triamide / 3 h / 100 °C

6: 99 percent / NaBH₄ / ethanol / 0.5 h / 0 °C

7: 95 percent / triethylamine / CH₂Cl₂ / 2 h / 0 °C

8: 93 percent / NaBH₄ / propan-2-ol / 80 °C

9: H₂ / Raney nickel / ethyl acetate / 96 h / 90007.2 Torr

With sodium tetrahydroborate; sodium azide; oxalyl dichloride; 15-crown-5; tetrabutylammomium bromide; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; bis(tri-n-butyltin)oxide; lithium diisopropyl amide; nickel; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; hexane; dichloromethane; ethyl acetate; isopropyl alcohol; benzene;

DOI:10.1016/S0040-4020(97)00240-8

Reference yield:

1-((3aR,5aS,8aS,8bR)-2,2,7,7-Tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethane-1,2-diol → (R)-2-Benzyloxy-1-methyl-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethylamine (189571-95-7)

Guidance literature:

Multi-step reaction with 9 steps

1: 89 percent / bis-tributylstannyl oxide, tetrabutylammonium bromide / benzene / 24 h / Heating

2: 95 percent / oxalyl chloride, DMSO, triethylamine / CH₂Cl₂ / 2 h / Ambient temperature

3: 82 percent / lithium diisopropylamide / tetrahydrofuran; hexane / -78 - 20 °C

4: 93 percent / sodium hydride / tetrahydrofuran / 12 h / Ambient temperature

5: 93 percent / sodium azide, 15-crown-5 / hexamethylphosphoric acid triamide / 3 h / 100 °C

6: 99 percent / NaBH₄ / ethanol / 0.5 h / 0 °C

7: 95 percent / triethylamine / CH₂Cl₂ / 2 h / 0 °C

8: 93 percent / NaBH₄ / propan-2-ol / 80 °C

9: H₂ / Raney nickel / ethyl acetate / 96 h / 90007.2 Torr

With sodium tetrahydroborate; sodium azide; oxalyl dichloride; 15-crown-5; tetrabutylammomium bromide; hydrogen; sodium hydride; dimethyl sulfoxide; triethylamine; bis(tri-n-butyltin)oxide; lithium diisopropyl amide; nickel; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; hexane; dichloromethane; ethyl acetate; isopropyl alcohol; benzene;

DOI:10.1016/S0040-4020(97)00240-8

upstream raw materials:

(R)-2-Benzyloxymethyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-aziridine

benzyl bromide

2-Benzyloxy-1-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethanol

2-Benzyloxy-1-((3aR,5S,5aR,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-yl)-ethanone

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