(R)-2-Azido-3-benzyloxy-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)-propan-1-ol

Base Information

• Chemical Name: (R)-2-Azido-3-benzyloxy-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)-propan-1-ol
• CAS No.: 189571-90-2
• Molecular Formula: C₂₁H₂₉N₃O₇
• Molecular Weight: 435.477

Synonyms:(R)-2-Azido-3-benzyloxy-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)-propan-1-ol

Chemical Property of (R)-2-Azido-3-benzyloxy-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)-propan-1-ol

Chemical Property:

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Safty Information:

• Pictogram(s):  
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Technology Process of (R)-2-Azido-3-benzyloxy-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)-propan-1-ol

There total 7 articles about (R)-2-Azido-3-benzyloxy-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)-propan-1-ol 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: 99.0%

(R)-2-Azido-3-benzyloxy-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)-propionaldehyde (189571-89-9) → (R)-2-Azido-3-benzyloxy-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)-propan-1-ol (189571-90-2)

Guidance literature:

With sodium tetrahydroborate; In ethanol; at 0 ℃; for 0.5h;

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

Reference yield:

benzyl bromide (100-39-0) → (R)-2-Azido-3-benzyloxy-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)-propan-1-ol (189571-90-2)

Guidance literature:

Multi-step reaction with 6 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

With sodium tetrahydroborate; sodium azide; oxalyl dichloride; 15-crown-5; tetrabutylammomium bromide; sodium hydride; dimethyl sulfoxide; triethylamine; bis(tri-n-butyltin)oxide; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; hexane; dichloromethane; 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-Azido-3-benzyloxy-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)-propan-1-ol (189571-90-2)

Guidance literature:

Multi-step reaction with 6 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

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

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

upstream raw materials:

(R)-2-Azido-3-benzyloxy-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)-propionaldehyde

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

Downstream raw materials:

Methanesulfonic acid (S)-2-azido-3-benzyloxy-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)-propyl ester

(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

(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

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