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

Base Information

• Chemical Name: methyl 4-(benzyl(hydroxy)amino)-4-((4S,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)butanoate
• CAS No.: 1319211-60-3
• Molecular Formula: C₂₂H₃₃NO₇
• Molecular Weight: 423.507
• Mol file: 1319211-60-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 6 articles about methyl 4-(benzyl(hydroxy)amino)-4-((4S,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)butanoate 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: 99.0%

(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) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → 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)

Guidance literature:

With samarium diiodide; water; In tetrahydrofuran; at -88 - -81 ℃; for 1h; optical yield given as %de; diastereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tet.2011.05.129

Reference yield:

2,3:4,5-di-O-isopropylidene-aldehydo-D-ribose (50866-82-5) → 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)

Guidance literature:

Multi-step reaction with 2 steps

1: magnesium sulfate / dichloromethane / 15 h / 20 °C

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

With samarium diiodide; water; magnesium sulfate; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tet.2011.05.129

Reference yield:

(4R,4'R,5R)-5-(bis(isopropylthio)methyl)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolane) (1319211-62-5) → 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)

Guidance literature:

Multi-step reaction with 3 steps

1: water; mercury dichloride; mercury(II) oxide / acetone / 2 h / Reflux

2: magnesium sulfate / dichloromethane / 15 h / 20 °C

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

With samarium diiodide; water; magnesium sulfate; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; dichloromethane; acetone;

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

acrylic acid methyl ester

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

(S)-1-benzyl-5-((4S,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)pyrrolidin-2-one

1-benzyl-2-((4S,4'R,5S)-2,2,2',2'-tetramethyl-4,4'-bi(1,3-dioxolan)-5-yl)pyrrolidine

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