(5S,1'S)-5-<1'--2'-phenylethyl>dihydrofuran-2(3H)-one

Base Information

• Chemical Name: (5S,1'S)-5-<1'--2'-phenylethyl>dihydrofuran-2(3H)-one
• CAS No.: 145655-07-8
• Molecular Formula: C₂₄H₂₉NO₄
• Molecular Weight: 395.499
• Mol file: 145655-07-8.mol

Synonyms:(5S,1'S)-5-<1'--2'-phenylethyl>dihydrofuran-2(3H)-one

Chemical Property of (5S,1'S)-5-<1'--2'-phenylethyl>dihydrofuran-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,1'S)-5-<1'--2'-phenylethyl>dihydrofuran-2(3H)-one

There total 16 articles about (5S,1'S)-5-<1'--2'-phenylethyl>dihydrofuran-2(3H)-one 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: 86.0%

Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-6-phenylhexanoate (145655-06-7) → (5S,1'S)-5-<1'--2'-phenylethyl>dihydrofuran-2(3H)-one (145655-07-8)

Guidance literature:

With tetrabutyl ammonium fluoride; water; In tetrahydrofuran; for 4h; Ambient temperature;

DOI:10.1016/S0040-4039(00)60888-2

Reference yield:

(E)-(S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-6-phenyl-hex-2-enoic acid methyl ester (145655-04-5) → (5S,1'S)-5-<1'--2'-phenylethyl>dihydrofuran-2(3H)-one (145655-07-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 88 percent / H₂ / Pd/BaSO₄ / methanol / 4 h / 760 Torr / Ambient temperature

2: NaBH₄ / methanol / 2 h / -50 °C

With sodium tetrahydroborate; hydrogen; Pd-BaSO₄; In methanol;

DOI:10.1016/S0040-4039(00)60888-2

Reference yield:

(E)-(4S,5S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-hydroxy-6-phenyl-hex-2-enoic acid methyl ester (145655-03-4) → (5S,1'S)-5-<1'--2'-phenylethyl>dihydrofuran-2(3H)-one (145655-07-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / Ac₂O/DMSO / 18 h / Ambient temperature

2: 88 percent / H₂ / Pd/BaSO₄ / methanol / 4 h / 760 Torr / Ambient temperature

3: NaBH₄ / methanol / 2 h / -50 °C

With sodium tetrahydroborate; hydrogen; acetic anhydride; dimethyl sulfoxide; Pd-BaSO₄; In methanol;

DOI:10.1016/S0040-4039(00)60888-2

upstream raw materials:

(S)-5-(Benzyl-tert-butoxycarbonyl-amino)-4-oxo-6-phenyl-hexanoic acid methyl ester

Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-6-phenylhexanoate

(1'R,2'S)-2-<2-(N-benzyl-N-tert-butoxycarbonylamino)-1-hydroxy-3-phenylpropyl>-1,3-thiazole

(2R,3S)-3--2-<(tert-butyldimethylsilyl)oxy>-4-phenylbutanal

Downstream raw materials:

(3R,5S,1'S)-3-Benzyl-5-<1'--2'-phenylethyl>dihydrofuran-2(3H)-one

(3R,5S)-3-benzyl-5-{(1S)-1-[(tert-butoxycarbonyl)amino]-2-phenylethyl}dihydrofuran-2-(3H)-one

(3R,5S,1'S)-3-Benzyl-5-<1'--2'-phenylethyl>dihydrofuran-2(3H)-one