(2R,3S)-2,3-Dimethyl-5-oxo-tetrahydro-furan-2-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester

Base Information

• Chemical Name: (2R,3S)-2,3-Dimethyl-5-oxo-tetrahydro-furan-2-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester
• CAS No.: 76405-16-8
• Molecular Formula: C₁₅H₂₁NO₅
• Molecular Weight: 295.335
• Mol file: 76405-16-8.mol

Synonyms:

Chemical Property of (2R,3S)-2,3-Dimethyl-5-oxo-tetrahydro-furan-2-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S)-2,3-Dimethyl-5-oxo-tetrahydro-furan-2-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester

There total 13 articles about (2R,3S)-2,3-Dimethyl-5-oxo-tetrahydro-furan-2-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester 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: 32.0%

S-tert-butyl γ-hydroxy-β,γ-dimethyl-δ-oxoimidazole-1-thiovalerate (76405-14-6) + retronecine (480-85-3) → (2R,3S)-2,3-Dimethyl-5-oxo-tetrahydro-furan-2-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester (76405-16-8)

Guidance literature:

In tetrahydrofuran; for 24h; Ambient temperature;

DOI:10.1021/ja00394a022

Reference yield: 21.0%

(4S,5R,13aR,13bR)-4,5,8,10,12,13,13a,13b-octahydro-5-hydroxy-4,5-dimethyl-2H-<1,6>dioxacycloundecino<2,3,4-gh>pyrrolizidine-2,6(3H)-dione 5-acetate (76465-88-8) → (2R,3S)-2,3-Dimethyl-5-oxo-tetrahydro-furan-2-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester (76405-16-8) + (4aR,8S,9R,12bR)-9-Hydroxy-8,9-dimethyl-2,3,4,4a,8,9,12,12b-octahydro-7H-5,11-dioxa-2a-aza-cycloundeca[cd]pentalene-6,10-dione (49679-23-4) + retronecine (480-85-3)

Guidance literature:

With hydrogenchloride; for 0.333333h; Heating;

DOI:10.1021/ja00394a022

Reference yield:

monocrotaline (315-22-0) → (2R,3S)-2,3-Dimethyl-5-oxo-tetrahydro-furan-2-carboxylic acid (7R,7aR)-7-hydroxy-5,6,7,7a-tetrahydro-3H-pyrrolizin-1-ylmethyl ester (76405-16-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 2.4 g / barium hydroxide octahydrate / H₂O / 5 h / Heating

2: 32 percent / tetrahydrofuran / 24 h / Ambient temperature

With barium hydroxide octahydrate; In tetrahydrofuran; water;

DOI:10.1021/ja00394a022

upstream raw materials:

(4S,5R,13aR,13bR)-4,5,8,10,12,13,13a,13b-octahydro-5-hydroxy-4,5-dimethyl-2H-<1,6>dioxacycloundecino<2,3,4-gh>pyrrolizidine-2,6(3H)-dione 5-acetate

S-tert-butyl γ-hydroxy-β,γ-dimethyl-δ-oxoimidazole-1-thiovalerate

retronecine

ethyl 3-methyl-4-oxopentanoate