ethyl (5R,7R,9S)-5-hydroxy-7,9-isopropylidenedioxy-3-oxo-11-phenylundecanoate

Base Information

Chemical Name:ethyl (5R,7R,9S)-5-hydroxy-7,9-isopropylidenedioxy-3-oxo-11-phenylundecanoate
CAS No.:695177-19-6
Molecular Formula:C₂₂H₃₂O₆
Molecular Weight:392.492
Hs Code.:

Synonyms:ethyl (5R,7R,9S)-5-hydroxy-7,9-isopropylidenedioxy-3-oxo-11-phenylundecanoate

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Chemical Property of ethyl (5R,7R,9S)-5-hydroxy-7,9-isopropylidenedioxy-3-oxo-11-phenylundecanoate

Chemical Property:

Purity/Quality:

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Technology Process of ethyl (5R,7R,9S)-5-hydroxy-7,9-isopropylidenedioxy-3-oxo-11-phenylundecanoate

There total 9 articles about ethyl (5R,7R,9S)-5-hydroxy-7,9-isopropylidenedioxy-3-oxo-11-phenylundecanoate 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:

: 502690-42-8
ethyl (3R,5S)-3,5-isopropylidenedioxy-7-phenylheptanoate

: 695177-19-6
ethyl (5R,7R,9S)-5-hydroxy-7,9-isopropylidenedioxy-3-oxo-11-phenylundecanoate

Guidance literature:: Multi-step reaction with 6 steps

1: 425 mg / LiBH₄; trimethoxyborane / diethyl ether / 1 h / 20 °C

2: 250 mg / N-methylmorpholine-N-oxide; 4 Angstroem molecular sieves; TPAP / acetonitrile / 1 h / 20 °C

3: i-Pr₂NEt; LiCl / acetonitrile / 20 °C

4: 100 percent / Sm(OiPr)3; 4 Angstroem molecular sieves; AsPh₃ / (R)-BINOL; tert-butyl hydroperoxide / tetrahydrofuran; decane / 20 °C

5: tetrahydrofuran / -78 °C

6: PhSeSePh; NaBH₄ / ethanol

With sodium tetrahydroborate; lithium borohydride; tetrapropylammonium perruthennate; Trimethyl borate; triphenyl-arsane; 4 A molecular sieve; diphenyl diselenide; samarium(III) isopropoxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; lithium chloride; tert.-butylhydroperoxide; (R)-1,1'-Bi-2-naphthol; In tetrahydrofuran; diethyl ether; decane; ethanol; acetonitrile;
DOI:10.1002/chem.200305709

Reference yield:

: ((4S,6S)-2,2-Dimethyl-6-phenethyl-[1,3]dioxan-4-yl)-acetaldehyde

: 695177-19-6
ethyl (5R,7R,9S)-5-hydroxy-7,9-isopropylidenedioxy-3-oxo-11-phenylundecanoate

Guidance literature:: Multi-step reaction with 4 steps

1: DBU; LiCl

2: 100 percent / Sm(OiPr)3; 4 Angstroem molecular sieves; AsPh₃ / (R)-BINOL; tert-butyl hydroperoxide / tetrahydrofuran; decane / 20 °C

3: tetrahydrofuran / -78 °C

4: PhSeSePh; NaBH₄ / ethanol

With sodium tetrahydroborate; triphenyl-arsane; 4 A molecular sieve; diphenyl diselenide; samarium(III) isopropoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; tert.-butylhydroperoxide; (R)-1,1'-Bi-2-naphthol; In tetrahydrofuran; decane; ethanol;
DOI:10.1002/chem.200305709

Reference yield:

: 2-((S)-2,2-Dimethyl-6-phenethyl-[1,3]dioxan-4-yl)-ethanol

: 695177-19-6
ethyl (5R,7R,9S)-5-hydroxy-7,9-isopropylidenedioxy-3-oxo-11-phenylundecanoate

Guidance literature:: Multi-step reaction with 5 steps

1: 250 mg / N-methylmorpholine-N-oxide; 4 Angstroem molecular sieves; TPAP / acetonitrile / 1 h / 20 °C

2: i-Pr₂NEt; LiCl / acetonitrile / 20 °C

3: 100 percent / Sm(OiPr)3; 4 Angstroem molecular sieves; AsPh₃ / (R)-BINOL; tert-butyl hydroperoxide / tetrahydrofuran; decane / 20 °C

4: tetrahydrofuran / -78 °C

5: PhSeSePh; NaBH₄ / ethanol

With sodium tetrahydroborate; tetrapropylammonium perruthennate; triphenyl-arsane; 4 A molecular sieve; diphenyl diselenide; samarium(III) isopropoxide; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; lithium chloride; tert.-butylhydroperoxide; (R)-1,1'-Bi-2-naphthol; In tetrahydrofuran; decane; ethanol; acetonitrile;
DOI:10.1002/chem.200305709