(-)-8-benzyloxy-swainsonine

Base Information

• Chemical Name: (-)-8-benzyloxy-swainsonine
• CAS No.: 162470-36-2
• Molecular Formula: C₁₅H₂₁NO₃
• Molecular Weight: 263.337
• Mol file: 162470-36-2.mol

Synonyms:(-)-8-benzyloxy-swainsonine

Chemical Property of (-)-8-benzyloxy-swainsonine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (-)-8-benzyloxy-swainsonine

There total 26 articles about (-)-8-benzyloxy-swainsonine 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:

(8R,8aS)-8-benzyloxy-3,5,6,7,8,8a-hexahydroindolizine (476171-52-5) → (-)-8-benzyloxy-swainsonine (162470-36-2)

Guidance literature:

With potassium osmate(VI); Hydroquinone 1,4-phthalazinediyl diether; potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In water; tert-butyl alcohol; at 4 ℃; for 168h;

DOI:10.1021/jo025977w

Reference yield:

6-[(4-methoxyphenyl)methoxy]-(2R,3R)-epoxyhexan-1-al (476171-68-3) → (-)-8-benzyloxy-swainsonine (162470-36-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: KHMDS / toluene / 0.08 h / 0 °C

1.2: 2.76 g / toluene / 3 h / 0 - 20 °C

2.1: 88.2 percent / p-toluenesulfonic acid monohydrate / 72 h / 105 °C

3.1: 98 percent / triethylamine / tetrahydrofuran / 24 h / 20 °C

4.1: 95.2 percent / benzylidene-bis(tricyclohexylphosphine)dichlororuthenium / CH₂Cl₂ / 20 h / Heating

5.1: 74.2 percent / sodium hydride; tetrabutylammonium iodide / tetrahydrofuran / 48 h / 20 °C

6.1: 88.1 percent / trifluoroacetic acid; anisole / CH₂Cl₂ / 1.5 h / 20 °C

7.1: triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 0.17 h / 0 °C

7.2: 73.7 percent / triethylamine / CH₂Cl₂ / 120 h / 4 °C

8.1: hydroquinine 1,4-phthalazinediyl diether; K₃Fe(CN)6; K₂OsO₄*2H₂O / K₂CO₃; methanesulfonamide / H₂O; 2-methyl-propan-2-ol / 168 h / 4 °C

With potassium osmate(VI); Grubbs catalyst first generation; Hydroquinone 1,4-phthalazinediyl diether; carbon tetrabromide; tetra-(n-butyl)ammonium iodide; potassium hexamethylsilazane; sodium hydride; toluene-4-sulfonic acid; methoxybenzene; triethylamine; triphenylphosphine; trifluoroacetic acid; potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In tetrahydrofuran; dichloromethane; water; toluene; tert-butyl alcohol;

DOI:10.1021/jo025977w

Reference yield:

(2S)-((1'R)-phenylmethoxy-4'-hydroxybutyl)-2,5-dihydropyrrole (476171-51-4) → (-)-8-benzyloxy-swainsonine (162470-36-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 0.17 h / 0 °C

1.2: 73.7 percent / triethylamine / CH₂Cl₂ / 120 h / 4 °C

2.1: hydroquinine 1,4-phthalazinediyl diether; K₃Fe(CN)6; K₂OsO₄*2H₂O / K₂CO₃; methanesulfonamide / H₂O; 2-methyl-propan-2-ol / 168 h / 4 °C

With potassium osmate(VI); Hydroquinone 1,4-phthalazinediyl diether; carbon tetrabromide; triphenylphosphine; potassium hexacyanoferrate(III); methanesulfonamide; potassium carbonate; In dichloromethane; water; tert-butyl alcohol;

DOI:10.1021/jo025977w

upstream raw materials:

(2S,3R,7S,8R)-3-benzyloxy-1-tosyl-2-(1',2',3'-trihydroxypropyl)piperidine

(8R,8aS)-8-benzyloxy-3,5,6,7,8,8a-hexahydroindolizine

6-[(4-methoxyphenyl)methoxy]-(2R,3R)-epoxyhexan-1-al

(2S)-((1'R)-phenylmethoxy-4'-hydroxybutyl)-2,5-dihydropyrrole

Downstream raw materials:

(3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-9-(phenylmethoxy)-1,3-dioxolo[4,5-a]indolizine

swainsonine

(3aR,9R,9aR,9bS)-octahydro-2,2-dimethyl-[1,3]dioxolo[4,5-a]indolizin-9-ol