1-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(diphenyl-phosphinoyl)-2-morpholin-4-yl-ethanol

Base Information

• Chemical Name: 1-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(diphenyl-phosphinoyl)-2-morpholin-4-yl-ethanol
• CAS No.: 127275-01-8
• Molecular Formula: C₃₀H₄₆NO₆PSi
• Molecular Weight: 575.758
• Mol file: 127275-01-8.mol

Synonyms:

Chemical Property of 1-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(diphenyl-phosphinoyl)-2-morpholin-4-yl-ethanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(diphenyl-phosphinoyl)-2-morpholin-4-yl-ethanol

There total 4 articles about 1-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(diphenyl-phosphinoyl)-2-morpholin-4-yl-ethanol 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:

4-<(Diphenylphosphinoyl)methyl>morpholine (20684-76-8) + (4R,5S)-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde (108817-97-6) → [(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetaldehyde (127275-00-7) + 1-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(diphenyl-phosphinoyl)-2-morpholin-4-yl-ethanol (127275-01-8)

Guidance literature:

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; In tetrahydrofuran; at 0 ℃; Yield given. Yields of byproduct given;

DOI:10.1016/S0040-4039(00)99133-0

Reference yield:

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate (59779-75-8) → 1-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(diphenyl-phosphinoyl)-2-morpholin-4-yl-ethanol (127275-01-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 65 percent / sodium borohydride

2: 87 percent / KH / tetrahydrofuran / 0 °C

3: 1.) DMSO, oxalyl chloride; 2.) triethylamine / 1.) -78 deg C

4: n-BuLi, HMPA / tetrahydrofuran / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; potassium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)99133-0

Reference yield:

2,3-O-isopropylidene-L-threitol (50622-09-8) → 1-[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-(diphenyl-phosphinoyl)-2-morpholin-4-yl-ethanol (127275-01-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 87 percent / KH / tetrahydrofuran / 0 °C

2: 1.) DMSO, oxalyl chloride; 2.) triethylamine / 1.) -78 deg C

3: n-BuLi, HMPA / tetrahydrofuran / 0 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; oxalyl dichloride; potassium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)99133-0

upstream raw materials:

4-<(Diphenylphosphinoyl)methyl>morpholine

(4R,5S)-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-1,3-dioxolane-4-carbaldehyde

diethyl (4R,5R)-2,2-dimethyl-1,3-dioxolane-4,5-dicarboxylate

2,3-O-isopropylidene-L-threitol

Downstream raw materials:

(2E,6Z)-(S)-4-Hydroxy-dodeca-2,6-dienal

1-[(4S,5S)-2,2-Dimethyl-5-((Z)-oct-2-enyl)-[1,3]dioxolan-4-yl]-2-(diphenyl-phosphinoyl)-2-morpholin-4-yl-ethanol