swainsonine tribenzylate

Base Information

• Chemical Name: swainsonine tribenzylate
• CAS No.: 90706-28-8
• Molecular Formula: C₂₉H₃₃NO₃
• Molecular Weight: 443.586
• Mol file: 90706-28-8.mol

Synonyms:swainsonine tribenzylate

Chemical Property of swainsonine tribenzylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of swainsonine tribenzylate

There total 17 articles about swainsonine tribenzylate 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: 74.0%

(1S,2R,8R,8aR)-1,2,8-tris(benzyloxy)hexahydroindolizin-5(1H)-one (107741-02-6,107741-05-9,90706-29-9) → swainsonine tribenzylate (90706-28-8)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran;

DOI:10.1246/cl.1984.513

Reference yield:

N-[(1S,2S,3R)-1-((S)-2,2-Bis-ethylsulfanyl-1-hydroxy-ethyl)-2,3,4-trihydroxy-butyl]-acetamide (22617-60-3,22738-78-9) → swainsonine tribenzylate (90706-28-8)

Guidance literature:

Multi-step reaction with 10 steps

1: 4-dimethylaminopyridine / pyridine / 3.5 h / 70 °C

2: 1.) sodium hydride / 1.) DMF, 20 min; 2.) DMF, overnight

3: toluene-p-sulfonic acid monohydrate / methanol / 2 h

4: 77 percent / pyridine / 16 h

5: 93 percent / aq. sodium hydroxide / dioxane / 0.5 h / Heating

6: mercury(II) chloride, calcium carbonate / H₂O; acetonitrile / 0.83 h

7: 2 percent / 60percent sodium hydride in mineral oil / tetrahydrofuran / 4 h

8: 70 percent / H₂ / Raney nickel / ethanol / 2 h

9: 54 percent / 15M KOH / aq. ethanol / 144 h / 90 °C

10: 74 percent / lithium aluminum hydride / tetrahydrofuran / 5 h / Heating

With pyridine; dmap; potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; hydrogen; sodium hydride; toluene-4-sulfonic acid; calcium carbonate; mercury dichloride; nickel; In tetrahydrofuran; 1,4-dioxane; pyridine; methanol; ethanol; water; acetonitrile;

DOI:10.1016/0008-6215(85)85186-7

Reference yield:

3-acetamido-2,4,5-tri-O-benzyl-3-deoxy-6-O-tosyl-D-mannose diethyl dithioacetal (90706-23-3) → swainsonine tribenzylate (90706-28-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 93 percent / aq. sodium hydroxide / dioxane / 0.5 h / Heating

2: mercury(II) chloride, calcium carbonate / H₂O; acetonitrile / 0.83 h

3: 2 percent / 60percent sodium hydride in mineral oil / tetrahydrofuran / 4 h

4: 70 percent / H₂ / Raney nickel / ethanol / 2 h

5: 54 percent / 15M KOH / aq. ethanol / 144 h / 90 °C

6: 74 percent / lithium aluminum hydride / tetrahydrofuran / 5 h / Heating

With potassium hydroxide; sodium hydroxide; lithium aluminium tetrahydride; hydrogen; sodium hydride; calcium carbonate; mercury dichloride; nickel; In tetrahydrofuran; 1,4-dioxane; ethanol; water; acetonitrile;

DOI:10.1016/0008-6215(85)85186-7

upstream raw materials:

(1S,2R,8R,8aR)-1,2,8-tris(benzyloxy)hexahydroindolizin-5(1H)-one

Methyl 3-acetamido-4,6-O-benzylidene-3-deoxy-α-D-glucopyranoside

methyl 3-acetamido-2,4,6-tri-O-acetyl-3-deoxy-α-D-mannopyranoside

methyl 3-acetamido-4,6-O-benzylidene-3-deoxy-2-O-mesyl-α-D-glucopyranoside

Downstream raw materials:

swainsonine