(1R)-1-((4R,5S)-5-(1-benzylpyrrolidin-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol

Base Information

• Chemical Name: (1R)-1-((4R,5S)-5-(1-benzylpyrrolidin-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol
• CAS No.: 1319211-69-2
• Molecular Formula: C₁₈H₂₇NO₄
• Molecular Weight: 321.417
• Mol file: 1319211-69-2.mol

Synonyms:(1R)-1-((4R,5S)-5-(1-benzylpyrrolidin-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol

Chemical Property of (1R)-1-((4R,5S)-5-(1-benzylpyrrolidin-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R)-1-((4R,5S)-5-(1-benzylpyrrolidin-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol

There total 9 articles about (1R)-1-((4R,5S)-5-(1-benzylpyrrolidin-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol 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: 47.0%

1-benzyl-2-((4S,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)pyrrolidine (1319211-67-0) → (1R)-1-((4R,5S)-5-(1-benzylpyrrolidin-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol (1319211-69-2)

Guidance literature:

1-benzyl-2-((4S,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)pyrrolidine; With water; acetic acid; at 40 ℃; for 72h;

With potassium carbonate; In water; pH=> 10;

DOI:10.1016/j.tet.2011.05.129

Reference yield:

(Z)-1-phenyl-N-(((4S,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)methylene)methanamine N-oxide (1319211-61-4) → (1R)-1-((4R,5S)-5-(1-benzylpyrrolidin-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol (1319211-69-2)

Guidance literature:

Multi-step reaction with 4 steps

1.1: samarium diiodide; water / tetrahydrofuran / 1 h / -88 - -81 °C / Inert atmosphere

2.1: acetic acid; zinc / tetrahydrofuran; water / 1.5 h / 50 °C

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux

3.2: 20 °C / Inert atmosphere

4.1: water; acetic acid / 72 h / 40 °C

4.2: pH > 10

With lithium aluminium tetrahydride; samarium diiodide; water; acetic acid; zinc; In tetrahydrofuran; water;

DOI:10.1016/j.tet.2011.05.129

Reference yield:

methyl 4-(benzyl(hydroxy)amino)-4-((4S,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)butanoate (1319211-60-3) → (1R)-1-((4R,5S)-5-(1-benzylpyrrolidin-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)ethane-1,2-diol (1319211-69-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetic acid; zinc / tetrahydrofuran; water / 1.5 h / 50 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux

2.2: 20 °C / Inert atmosphere

3.1: water; acetic acid / 72 h / 40 °C

3.2: pH > 10

With lithium aluminium tetrahydride; water; acetic acid; zinc; In tetrahydrofuran; water;

DOI:10.1016/j.tet.2011.05.129

upstream raw materials:

2,3:4,5-di-O-isopropylidene-aldehydo-D-ribose

(4R,4'R,5R)-5-(bis(isopropylthio)methyl)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolane)

(Z)-1-phenyl-N-(((4S,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)methylene)methanamine N-oxide

methyl 4-(benzyl(hydroxy)amino)-4-((4S,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)butanoate

Downstream raw materials:

(3aR,4S,8aS,8bS)-5-benzyl-4-((tert-butyldimethylsilyloxy)methyl)-2,2-dimethyloctahydro-[1,3]dioxolo[4,5-a]pyrrolizin-5-ium chloride

(1R)-1-((4R,5S)-5-(1-benzylpyrrolidin-2-yl)-2,2-dimethyl-1,3-dioxolan-4-yl)-2-(tert-butyldimethylsilyloxy)ethanol