(S)-dimethyl 6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-oxohexylphosphonate

Base Information

• Chemical Name: (S)-dimethyl 6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-oxohexylphosphonate
• CAS No.: 1403354-19-7
• Molecular Formula: C₂₁H₃₇O₆PSi
• Molecular Weight: 444.58
• Mol file: 1403354-19-7.mol

Synonyms:(S)-dimethyl 6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-oxohexylphosphonate

Chemical Property of (S)-dimethyl 6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-oxohexylphosphonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-dimethyl 6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-oxohexylphosphonate

There total 2 articles about (S)-dimethyl 6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-oxohexylphosphonate 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:

C21H39O6PSi → (S)-dimethyl 6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-oxohexylphosphonate (1403354-19-7)

Guidance literature:

With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; at 20 ℃; for 1h; Ionic liquid;

DOI:10.1021/jo301425c

Reference yield:

(3S)-5-benzyloxy-3-(tert-butyldimethylsilyl)oxypentanal (198754-78-8) → (S)-dimethyl 6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-oxohexylphosphonate (1403354-19-7)

Guidance literature:

Multi-step reaction with 2 steps

1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

2: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1 h / 20 °C / Ionic liquid

With n-butyllithium; sodium hydrogencarbonate; Dess-Martin periodane; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo301425c

Reference yield: 77.0%

(3S,5S,7S)-7-(benzyloxy)-5-methoxy-3-methyldecanal (1035455-30-1) + (S)-dimethyl 6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-oxohexylphosphonate (1403354-19-7) → (3S,9R,11S,13S,E)-1,13-bis(benzyloxy)-3-(tert-butyldimethylsilyloxy)-11-methoxy-9-methylhexadec-6-en-5-one (1403354-25-5)

Guidance literature:

(S)-dimethyl 6-(benzyloxy)-4-(tert-butyldimethylsilyloxy)-2-oxohexylphosphonate; With N-ethyl-N,N-diisopropylamine; lithium chloride; In acetonitrile; at 20 ℃; for 0.5h;

(3S,5S,7S)-7-(benzyloxy)-5-methoxy-3-methyldecanal; In acetonitrile; for 12h; Inert atmosphere;

DOI:10.1021/jo301425c

upstream raw materials:

(3S)-5-benzyloxy-3-(tert-butyldimethylsilyl)oxypentanal

Downstream raw materials:

(2R,6S)-2-((2S,4S,6S)-6-(benzyloxy)-4-methoxy-2-methylnonyl)-6-(2-(benzyloxy)ethyl)dihydro-2H-pyran-4(3H)-one

(2S,6S)-2-((2S,4S,6S)-6-(benzyloxy)-4-methoxy-2-methylnonyl)-6-(2-(benzyloxy)ethyl)dihydro-2H-pyran-4(3H)-one

(3S,9R,11S,13S,E)-1,13-bis(benzyloxy)-3-hydroxy-11-methoxy-9-methylhexadec-6-en-5-one

(3S,9R,11S,13S,E)-1,13-bis(benzyloxy)-3-(tert-butyldimethylsilyloxy)-11-methoxy-9-methylhexadec-6-en-5-one