(5R,6R,7R,7aR)-6,7-bis-benzyloxy-5-benzyloxymethylhexahydropyrrolizin-3-one

Base Information

• Chemical Name: (5R,6R,7R,7aR)-6,7-bis-benzyloxy-5-benzyloxymethylhexahydropyrrolizin-3-one
• CAS No.: 537030-28-7
• Molecular Formula: C₂₉H₃₁NO₄
• Molecular Weight: 457.569
• Mol file: 537030-28-7.mol

Synonyms:(5R,6R,7R,7aR)-6,7-bis-benzyloxy-5-benzyloxymethylhexahydropyrrolizin-3-one

Chemical Property of (5R,6R,7R,7aR)-6,7-bis-benzyloxy-5-benzyloxymethylhexahydropyrrolizin-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,6R,7R,7aR)-6,7-bis-benzyloxy-5-benzyloxymethylhexahydropyrrolizin-3-one

There total 11 articles about (5R,6R,7R,7aR)-6,7-bis-benzyloxy-5-benzyloxymethylhexahydropyrrolizin-3-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: 87.0%

(2R,3R,4R,5R)-1-tert-butyloxycarbonyl 3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-[(2-ethyloxycarbonyl)ethyl]pyrrolidine (1310339-94-6) → (5R,6R,7R,7aR)-6,7-bis-benzyloxy-5-benzyloxymethylhexahydropyrrolizin-3-one (537030-28-7)

Guidance literature:

(2R,3R,4R,5R)-1-tert-butyloxycarbonyl 3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-[(2-ethyloxycarbonyl)ethyl]pyrrolidine; With hydrogenchloride; In water; ethyl acetate; at 0 - 20 ℃;

With potassium carbonate; In methanol; water; for 48h;

DOI:10.1021/jo200600n

Reference yield: 59.0%

ethyl acrylate (140-88-5,9003-32-1) + (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide (537030-19-6) → (5R,6R,7R,7aR)-6,7-bis-benzyloxy-5-benzyloxymethylhexahydropyrrolizin-3-one (537030-28-7)

Guidance literature:

ethyl acrylate; (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide; With samarium diiodide; water; In tetrahydrofuran; at -78 - 20 ℃;

With potassium carbonate; In ethanol; water; for 48h;

DOI:10.1021/jo048237r

Reference yield:

ethyl acrylate (140-88-5,9003-32-1) + (2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide (537030-19-6) → (5R,6R,7R,7aR)-6,7-bis-benzyloxy-5-benzyloxymethylhexahydropyrrolizin-3-one (537030-28-7) + 3-((2R,3R,4R,5R)-3,4-bis-benzyloxy-2-benzyloxymethylpyrrolidin-2-yl)propionic acid ethyl ester

Guidance literature:

With samarium diiodide; water; In tetrahydrofuran; at -78 - 20 ℃;

DOI:10.1021/jo048237r

upstream raw materials:

ethyl acrylate

(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide

Methanesulfonic acid (1S,2S,3R)-2,3-bis-benzyloxy-1-benzyloxymethyl-4-hydroxyimino-butyl ester

C₄₂H₄₇NO₅Si

Downstream raw materials:

(5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-5,6,7,7a-tetrahydropyrrolizin-3-one

(1S,2S,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-1,2-dihydroxypyrrolizidin-3-one

(1R,2R,5R,6R,7R,7aR)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)-1,2-dihydroxypyrrolizidin-3-one

(1S,2S,5R,6R,7R,7aS)-1,2-bis(acetyloxy)-6,7-bis(benzyloxy)-5-(benzyloxymethyl)pyrrolizidin-3-one