[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetaldehyde

Base Information

• Chemical Name: [(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetaldehyde
• CAS No.: 127275-00-7
• Molecular Formula: C₁₄H₂₈O₄Si
• Molecular Weight: 288.459
• Mol file: 127275-00-7.mol

Synonyms:[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetaldehyde

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

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

[(benzyloxy)methyl](triphenyl)phosphonium chloride (75772-01-9) + [(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetaldehyde (127275-00-7) → ({(4S,5S)-5-[2-(benzyloxy)vinyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methoxy)(tert-butyl)dimethylsilane + ({(4S,5S)-5-[2-(benzyloxy)vinyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methoxy)(tert-butyl)dimethylsilane

Guidance literature:

[(benzyloxy)methyl](triphenyl)phosphonium chloride; With potassium tert-butylate; In tetrahydrofuran; at -78 - -30 ℃; for 1.5h;

[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetaldehyde; In tetrahydrofuran; at -30 ℃; for 0.5h; Overall yield = 12.8 g;

DOI:10.1055/s-0035-1561948

Reference yield:

(S)-4-benzyl-3-propionyl-2-oxazolidinone (131685-53-5,101711-78-8) + [(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetaldehyde (127275-00-7) → (S)-4-benzyl-3-{(2S,3R)-4-[(4S,5S)-5-tert-butyldimethylsilyloxymethyl-2,2-dimethyl-1,3-dioxolan-4-yl]-3-hydroxy-2-methylbutanoyl}oxazolidin-2-one

Guidance literature:

(S)-4-benzyl-3-propionyl-2-oxazolidinone; With titanium tetrachloride; In dichloromethane; at 0 ℃; for 0.25h; Inert atmosphere;

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 0.333333h; Inert atmosphere;

[(4S,5S)-5-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-acetaldehyde; In 1-methyl-pyrrolidin-2-one; dichloromethane; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00665

upstream raw materials:

4-<(Diphenylphosphinoyl)methyl>morpholine

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

Downstream raw materials:

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

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