(2S,5R)-1-benzyl 2-ethyl 5-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pyrrolidine-1,2-dicarboxylate

Base Information

• Chemical Name: (2S,5R)-1-benzyl 2-ethyl 5-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pyrrolidine-1,2-dicarboxylate
• CAS No.: 1293921-67-1
• Molecular Formula: C₂₈H₄₅NO₈Si
• Molecular Weight: 551.753
• Mol file: 1293921-67-1.mol

Synonyms:(2S,5R)-1-benzyl 2-ethyl 5-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pyrrolidine-1,2-dicarboxylate

Chemical Property of (2S,5R)-1-benzyl 2-ethyl 5-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pyrrolidine-1,2-dicarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R)-1-benzyl 2-ethyl 5-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pyrrolidine-1,2-dicarboxylate

There total 2 articles about (2S,5R)-1-benzyl 2-ethyl 5-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pyrrolidine-1,2-dicarboxylate 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: 50.0%

(2S,5R)-ethyl 5-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pyrrolidine-2-carboxylate (1293921-66-0) + benzyl chloroformate (501-53-1,94274-21-2) → (2S,5R)-1-benzyl 2-ethyl 5-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pyrrolidine-1,2-dicarboxylate (1293921-67-1)

Guidance literature:

With triethylamine; In methanol; at 0 - 20 ℃; for 8h; Inert atmosphere;

DOI:10.1016/j.carres.2010.12.022

Reference yield:

(3aR,3'S,4S,6R,6aR)-ethyl 6-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyldihydro-3aH-spiro[furo[3,4-d][1,3]dioxole-4,6'-tetrahydrooxazine]-3'-carboxylate (1268670-43-4) → (2S,5R)-1-benzyl 2-ethyl 5-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pyrrolidine-1,2-dicarboxylate (1293921-67-1)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen; boric acid; nickel; magnesium sulfate / methanol / 4 h / Reflux

2: triethylamine / methanol / 8 h / 0 - 20 °C / Inert atmosphere

With hydrogen; boric acid; nickel; magnesium sulfate; triethylamine; In methanol;

DOI:10.1016/j.carres.2010.12.022

Reference yield: 74.0%

(2S,5R)-1-benzyl 2-ethyl 5-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pyrrolidine-1,2-dicarboxylate (1293921-67-1) + methanesulfonyl chloride (124-63-0) → (2S,5R)-1-benzyl 2-ethyl 5-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-mesyloxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pyrrolidine-1,2-dicarboxylate (1293921-68-2)

Guidance literature:

With pyridine; dmap; at 0 ℃; for 1.5h; Inert atmosphere;

DOI:10.1016/j.carres.2010.12.022

upstream raw materials:

(3aR,3'S,4S,6R,6aR)-ethyl 6-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyldihydro-3aH-spiro[furo[3,4-d][1,3]dioxole-4,6'-tetrahydrooxazine]-3'-carboxylate

(2S,5R)-ethyl 5-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-hydroxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pyrrolidine-2-carboxylate

benzyl chloroformate

Downstream raw materials:

(2S,5R)-1-benzyl 2-ethyl 5-((4S,5S)-2,2-dimethyl-5-((S)-oxiran-2-yl)-1,3-dioxolan-4-yl)pyrrolidine-1,2-dicarboxylate

(2S,5R)-1-benzyl 2-ethyl 5-((4S,5R)-5-((R)-2-(tert-butyldimethylsilyloxy)-1-mesyloxyethyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pyrrolidine-1,2-dicarboxylate