(2R,3R,4R,5R)-1-tert-butyloxycarbonyl 3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-[(2-ethyloxycarbonyl)ethyl]pyrrolidine

Base Information

• Chemical Name: (2R,3R,4R,5R)-1-tert-butyloxycarbonyl 3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-[(2-ethyloxycarbonyl)ethyl]pyrrolidine
• CAS No.: 1310339-94-6
• Molecular Formula: C₃₆H₄₅NO₇
• Molecular Weight: 603.756
• Mol file: 1310339-94-6.mol

Synonyms:(2R,3R,4R,5R)-1-tert-butyloxycarbonyl 3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-[(2-ethyloxycarbonyl)ethyl]pyrrolidine

Chemical Property of (2R,3R,4R,5R)-1-tert-butyloxycarbonyl 3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-[(2-ethyloxycarbonyl)ethyl]pyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R)-1-tert-butyloxycarbonyl 3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-[(2-ethyloxycarbonyl)ethyl]pyrrolidine

There total 3 articles about (2R,3R,4R,5R)-1-tert-butyloxycarbonyl 3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-[(2-ethyloxycarbonyl)ethyl]pyrrolidine 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: 61.0%

(2R/S,3S,4R,5R)-1-tert-butyloxycarbonyl-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-2-(pyridin-2-ylthio)pyrrolidine + ethyl acrylate (140-88-5,9003-32-1) → (3R,4R,5R)-5-benzyloxymethyl-1-(tert-butoxycarbonyl)-3,4-dibenzyloxypyrrolidine (1310339-91-3) + (2R,3R,4R,5R)-1-tert-butyloxycarbonyl 3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-[(2-ethyloxycarbonyl)ethyl]pyrrolidine (1310339-94-6)

Guidance literature:

With samarium diiodide; boron trifluoride diethyl etherate; tert-butyl alcohol; In tetrahydrofuran; at -60 ℃; for 0.5h; Inert atmosphere;

DOI:10.1021/jo200600n

Reference yield:

(3S,4R,5R)-5-benzyloxymethyl-1-(tert-butoxycarbonyl)-3,4-dibenzyloxy-pyrrolidin-2-one (944544-00-7) → (2R,3R,4R,5R)-1-tert-butyloxycarbonyl 3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-[(2-ethyloxycarbonyl)ethyl]pyrrolidine (1310339-94-6)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium tetrahydroborate / methanol / 1 h / -13 °C

2: boron trifluoride diethyl etherate; calcium chloride / dichloromethane / 0 - 20 °C / Inert atmosphere

3: samarium diiodide; boron trifluoride diethyl etherate; tert-butyl alcohol / tetrahydrofuran / 0.5 h / -60 °C / Inert atmosphere

With sodium tetrahydroborate; samarium diiodide; boron trifluoride diethyl etherate; calcium chloride; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jo200600n

Reference yield:

C31H37NO6 (1329714-94-4) → (2R,3R,4R,5R)-1-tert-butyloxycarbonyl 3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-[(2-ethyloxycarbonyl)ethyl]pyrrolidine (1310339-94-6)

Guidance literature:

Multi-step reaction with 2 steps

1: boron trifluoride diethyl etherate; calcium chloride / dichloromethane / 0 - 20 °C / Inert atmosphere

2: samarium diiodide; boron trifluoride diethyl etherate; tert-butyl alcohol / tetrahydrofuran / 0.5 h / -60 °C / Inert atmosphere

With samarium diiodide; boron trifluoride diethyl etherate; calcium chloride; tert-butyl alcohol; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jo200600n

upstream raw materials:

(3S,4R,5R)-5-benzyloxymethyl-1-(tert-butoxycarbonyl)-3,4-dibenzyloxy-pyrrolidin-2-one

C₃₁H₃₇NO₆

ethyl acrylate

Downstream raw materials:

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

(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