(2R,3R,4R,5R)-tert-butyl 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(2-oxoethyl)pyrrolidine-1-carboxylate

Base Information

• Chemical Name: (2R,3R,4R,5R)-tert-butyl 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(2-oxoethyl)pyrrolidine-1-carboxylate
• CAS No.: 1567688-04-3
• Molecular Formula: C₃₃H₃₉NO₆
• Molecular Weight: 545.676
• Mol file: 1567688-04-3.mol

Synonyms:(2R,3R,4R,5R)-tert-butyl 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(2-oxoethyl)pyrrolidine-1-carboxylate

Chemical Property of (2R,3R,4R,5R)-tert-butyl 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(2-oxoethyl)pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4R,5R)-tert-butyl 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(2-oxoethyl)pyrrolidine-1-carboxylate

There total 4 articles about (2R,3R,4R,5R)-tert-butyl 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(2-oxoethyl)pyrrolidine-1-carboxylate 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: 92.0%

(2R,3R,4R,5R)-tert-butyl 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(2,3-dihydroxypropyl)pyrrolidine-1-carboxylate (1567688-03-2) → (2R,3R,4R,5R)-tert-butyl 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(2-oxoethyl)pyrrolidine-1-carboxylate (1567688-04-3)

Guidance literature:

With sodium periodate; In tetrahydrofuran; at 20 ℃; for 3h; Alkaline conditions;

Reference yield:

(2R,3R,4R,5R)-tert-butyl 2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidine-1-carboxylate (1567688-00-9) → (2R,3R,4R,5R)-tert-butyl 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(2-oxoethyl)pyrrolidine-1-carboxylate (1567688-04-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 16 h / 20 °C

2: sodium periodate / tetrahydrofuran / 3 h / 20 °C / Alkaline conditions

With sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; acetone;

Reference yield:

(2R,3R,4R)-3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-3,4-dihydro-2H-pyrrole 1-oxide (537030-19-6) → (2R,3R,4R,5R)-tert-butyl 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(2-oxoethyl)pyrrolidine-1-carboxylate (1567688-04-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: tetrahydrofuran / 16 h / 20 °C

2.1: zinc / methanol; acetic acid / 1 h / Reflux

2.2: 16 h / 20 °C

3.1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / water; acetone / 16 h / 20 °C

4.1: sodium periodate / tetrahydrofuran / 3 h / 20 °C / Alkaline conditions

With sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; zinc; In tetrahydrofuran; methanol; water; acetic acid; acetone;

upstream raw materials:

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

(2R,3R,4R,5R)-2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidin-1-ol

(2R,3R,4R,5R)-tert-butyl 2-allyl-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidine-1-carboxylate

(2R,3R,4R,5R)-tert-butyl 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(2,3-dihydroxypropyl)pyrrolidine-1-carboxylate

Downstream raw materials:

2-((2R,3R,4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)-1-(3-phenylpropyl)pyrrolidin-2-yl)-N-methylacetamide

2-((2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)acetic acid

(2R,3R,4R,5R)-tert-butyl 3,4-bis(benzyloxy)-2-((benzyloxy)methyl)-5-(2-(methylamino)-2-oxoethyl)pyrrolidine-1-carboxylate

2-((2R,3R,4R,5R)-3,4-bis(benzyloxy)-5-((benzyloxy)methyl)pyrrolidin-2-yl)-N-methylacetamide