(1S,2S,8S,8aR)-2-O-benzoyl-1,2,8-trihydroxyoctahydroindolizine

Base Information

• Chemical Name: (1S,2S,8S,8aR)-2-O-benzoyl-1,2,8-trihydroxyoctahydroindolizine
• CAS No.: 96625-39-7
• Molecular Formula: C₁₅H₁₉NO₄
• Molecular Weight: 277.32
• Mol file: 96625-39-7.mol

Synonyms:

Chemical Property of (1S,2S,8S,8aR)-2-O-benzoyl-1,2,8-trihydroxyoctahydroindolizine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,8S,8aR)-2-O-benzoyl-1,2,8-trihydroxyoctahydroindolizine

There total 8 articles about (1S,2S,8S,8aR)-2-O-benzoyl-1,2,8-trihydroxyoctahydroindolizine 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: 54.0%

sodium benzoate (532-32-1) + (1S,2R,8S,8aR)-2-O-mesyl-1,2,8-trihydroxyoctahydroindolizine (96625-38-6) → (1S,2S,8S,8aR)-2-O-benzoyl-1,2,8-trihydroxyoctahydroindolizine (96625-39-7,102101-36-0,149952-72-7)

Guidance literature:

In N,N-dimethyl-formamide; at 120 ℃; for 2h;

DOI:10.1246/cl.1985.31

Reference yield:

(R)-1-((3aR,5S,6S,6aR)-6-azido-2,2-dimethyltetrahydrofuro-[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol (22169-71-7) → (1S,2S,8S,8aR)-2-O-benzoyl-1,2,8-trihydroxyoctahydroindolizine (96625-39-7,102101-36-0,149952-72-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 78 percent / pyridine

2: trifluoroacetic acid; H₂O / 5.5 h / Ambient temperature

3: 71 percent / tetrahydrofuran / 2 h / Heating

4: 19 percent / H₂ / 10percent Pd-C / methanol / 2660 Torr / Ambient temperature

5: Me₃SiCl

6: 28 percent / BH₃*Me₂S / tetrahydrofuran / Heating

7: 54 percent / dimethylformamide / 2 h / 120 °C

With chloro-trimethyl-silane; dimethylsulfide borane complex; hydrogen; palladium on activated charcoal; In tetrahydrofuran; pyridine; methanol; water; N,N-dimethyl-formamide; trifluoroacetic acid;

DOI:10.1246/cl.1985.31

Reference yield:

3-azido-3-deoxy-1,2-O-isopropylidene-5,6-di-O-mesyl-α-D-glucofuranose (96625-41-1) → (1S,2S,8S,8aR)-2-O-benzoyl-1,2,8-trihydroxyoctahydroindolizine (96625-39-7,102101-36-0,149952-72-7)

Guidance literature:

Multi-step reaction with 6 steps

1: trifluoroacetic acid; H₂O / 5.5 h / Ambient temperature

2: 71 percent / tetrahydrofuran / 2 h / Heating

3: 19 percent / H₂ / 10percent Pd-C / methanol / 2660 Torr / Ambient temperature

4: Me₃SiCl

5: 28 percent / BH₃*Me₂S / tetrahydrofuran / Heating

6: 54 percent / dimethylformamide / 2 h / 120 °C

With chloro-trimethyl-silane; dimethylsulfide borane complex; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; water; N,N-dimethyl-formamide; trifluoroacetic acid;

DOI:10.1246/cl.1985.31

upstream raw materials:

sodium benzoate

(1S,2R,8S,8aR)-2-O-mesyl-1,2,8-trihydroxyoctahydroindolizine

(R)-1-((3aR,5S,6S,6aR)-6-azido-2,2-dimethyltetrahydrofuro-[2,3-d][1,3]dioxol-5-yl)ethane-1,2-diol

(1S,2R,8S,8aR)-2-O-mesyl-5-oxo-1,2,8-trihydroxyoctahydroindolizine