N-benzyl-(6R,1'S,2'S,3'R)-6-(1',2'-di-O-benzyl-3',4'-O-isopropylidene-1',2',3',4'-tetrahydroxy-1'-butyl)-2,3-didehydropiperidine-4-one

Base Information

• Chemical Name: N-benzyl-(6R,1'S,2'S,3'R)-6-(1',2'-di-O-benzyl-3',4'-O-isopropylidene-1',2',3',4'-tetrahydroxy-1'-butyl)-2,3-didehydropiperidine-4-one
• CAS No.: 160849-25-2
• Molecular Formula: C₃₃H₃₇NO₅
• Molecular Weight: 527.66
• Mol file: 160849-25-2.mol

Synonyms:N-benzyl-(6R,1'S,2'S,3'R)-6-(1',2'-di-O-benzyl-3',4'-O-isopropylidene-1',2',3',4'-tetrahydroxy-1'-butyl)-2,3-didehydropiperidine-4-one

Chemical Property of N-benzyl-(6R,1'S,2'S,3'R)-6-(1',2'-di-O-benzyl-3',4'-O-isopropylidene-1',2',3',4'-tetrahydroxy-1'-butyl)-2,3-didehydropiperidine-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N-benzyl-(6R,1'S,2'S,3'R)-6-(1',2'-di-O-benzyl-3',4'-O-isopropylidene-1',2',3',4'-tetrahydroxy-1'-butyl)-2,3-didehydropiperidine-4-one

There total 1 articles about N-benzyl-(6R,1'S,2'S,3'R)-6-(1',2'-di-O-benzyl-3',4'-O-isopropylidene-1',2',3',4'-tetrahydroxy-1'-butyl)-2,3-didehydropiperidine-4-one 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:

danishefsky's diene (54125-02-9) + Benzyl-[(2S,3S)-2,3-bis-benzyloxy-3-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-prop-(E)-ylidene]-amine → N-benzyl-(6S,1'S,2'S,3'R)-6-(1',2'-di-O-benzyl-3',4'-O-isopropylidene-1',2',3',4'-tetrahydroxy-1'-butyl)-2,3-didehydropiperidine-4-one + N-benzyl-(6R,1'S,2'S,3'R)-6-(1',2'-di-O-benzyl-3',4'-O-isopropylidene-1',2',3',4'-tetrahydroxy-1'-butyl)-2,3-didehydropiperidine-4-one (160849-25-2)

Guidance literature:

With zinc(II) chloride; In tetrahydrofuran; Product distribution; different azomethines and solvent;

DOI:10.1016/S0040-4020(01)85680-5

Reference yield: 95.0%

N-benzyl-(6R,1'S,2'S,3'R)-6-(1',2'-di-O-benzyl-3',4'-O-isopropylidene-1',2',3',4'-tetrahydroxy-1'-butyl)-2,3-didehydropiperidine-4-one (160849-25-2) → N-benzyl-(2R,4S,1'S,2'S,3'R)-2-(1',2'-di-O-benzyl-3',4'-O-isopropylidene-1',2',3',4'-tetrahydroxy-1'-butyl)-4-hydroxypiperidine

Guidance literature:

With sodium tetrahydroborate; In ethanol; for 16h; Ambient temperature;

DOI:10.1016/S0040-4020(01)85680-5

Reference yield:

N-benzyl-(6R,1'S,2'S,3'R)-6-(1',2'-di-O-benzyl-3',4'-O-isopropylidene-1',2',3',4'-tetrahydroxy-1'-butyl)-2,3-didehydropiperidine-4-one (160849-25-2) → N-benzyl-(2R,1'S,2'S,3'R)-2-(1',2'-di-O-benzyl-3',4'-O-isopropylidene-1',2',3',4'-tetrahydroxy-1'-butyl)-piperidine-4-one

Guidance literature:

With potassium hydroxide; dihydrogen peroxide; L-Selectride; Yield given. Multistep reaction; 1.) THF, -78 deg C, 1 h, -78 deg C to RT; 2.) ethanol, RT, 3 h;

DOI:10.1016/S0040-4020(01)85680-5

upstream raw materials:

danishefsky's diene