(2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-tert-butylpyrrolidine-2-carboxamide

Base Information

• Chemical Name: (2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-tert-butylpyrrolidine-2-carboxamide
• CAS No.: 1437657-55-0
• Molecular Formula: C₃₁H₃₈N₂O₄
• Molecular Weight: 502.654
• Mol file: 1437657-55-0.mol

Synonyms:(2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-tert-butylpyrrolidine-2-carboxamide

Chemical Property of (2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-tert-butylpyrrolidine-2-carboxamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-tert-butylpyrrolidine-2-carboxamide

There total 13 articles about (2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-tert-butylpyrrolidine-2-carboxamide 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: 74.0%

(2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-tert-butyl-1-(2,2,2-trifluoroacetyl)pyrrolidine-2-carboxamide → (2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-tert-butylpyrrolidine-2-carboxamide (1437657-55-0)

Guidance literature:

With water; sodium hydroxide; In methanol; at 20 ℃;

DOI:10.1021/acs.joc.5b00335

Reference yield: 44.0%

C36H44N2O5 (1437657-22-1) → (2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-tert-butylpyrrolidine-2-carboxamide (1437657-55-0)

Guidance literature:

With iodine; In tetrahydrofuran; water; for 0.5h;

DOI:10.1021/ol4012053

Reference yield:

benzyl bromide (100-39-0) → (2S,3S,4R,5R)-3,4-bis(benzyloxy)-5-[(benzyloxy)methyl]-N-tert-butylpyrrolidine-2-carboxamide (1437657-55-0)

Guidance literature:

Multi-step reaction with 11 steps

1.1: acetyl chloride

1.2: 2 h / 20 °C

2.1: sulfuric acid / acetic acid / 1 h / 100 °C

3.1: sodium tetrahydroborate / ethanol / 5 h / 0 - 20 °C

4.1: triethylamine; dmap / dichloromethane / 144 h

5.1: pyridine / 0 - 4 °C

6.1: sodium azide; 15-crown-5; tetra(n-butyl)ammonium hydrogensulfate / N,N-dimethyl-formamide / 48 h / 100 °C

7.1: toluene-4-sulfonic acid / methanol; chloroform / 6 h

8.1: Dess-Martin periodane / dichloromethane / 0 - 4 °C

9.1: trimethylphosphane / methanol; toluene / 1 h / 0 °C

10.1: methanol / 0 - 4 °C

11.1: iodine / water; tetrahydrofuran / 0.5 h

With pyridine; dmap; sodium tetrahydroborate; sodium azide; 15-crown-5; sulfuric acid; iodine; tetra(n-butyl)ammonium hydrogensulfate; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; acetyl chloride; trimethylphosphane; In tetrahydrofuran; methanol; ethanol; dichloromethane; chloroform; water; acetic acid; N,N-dimethyl-formamide; toluene; 10.1: |Ugi Condensation;

DOI:10.1021/ol4012053

upstream raw materials:

benzyl bromide

L-arabinofuranose

2,3,5-tri-O-benzyl-1-O-methyl-L-lyxofuranose

2,3,5-tri-O-benzyl-L-lyxitol