(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

Base Information

• Chemical Name: (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
• CAS No.: 1319211-61-4
• Molecular Formula: C₁₈H₂₅NO₅
• Molecular Weight: 335.4
• Mol file: 1319211-61-4.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 4 articles about (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 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:

2,3:4,5-di-O-isopropylidene-aldehydo-D-ribose (50866-82-5) + N-benzyl hydroxylalmine (622-30-0) → (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)

Guidance literature:

With magnesium sulfate; In dichloromethane; at 20 ℃; for 15h;

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) → (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)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

DOI:10.1016/j.tet.2011.05.129

Reference yield:

(2R,3R,4R)-5,5-bis(isopropylthio)pentane-1,2,3,4-tetraol (1071695-98-1) → (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)

Guidance literature:

Multi-step reaction with 3 steps

1: toluene-4-sulfonic acid / tetrahydrofuran / 3 h / 60 °C

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

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

With water; magnesium sulfate; toluene-4-sulfonic acid; 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

N-benzyl hydroxylalmine

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

(2R,3R,4R)-5,5-bis(isopropylthio)pentane-1,2,3,4-tetraol

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