(3R,5S,1'S)-5-<1'--3'-methylbutyl>-3-(2-methylprop-2-enyl)dihydrofuran-2(3H)-one

Base Information

• Chemical Name: (3R,5S,1'S)-5-<1'--3'-methylbutyl>-3-(2-methylprop-2-enyl)dihydrofuran-2(3H)-one
• CAS No.: 172329-61-2
• Molecular Formula: C₂₀H₂₉NO₂
• Molecular Weight: 315.456
• Mol file: 172329-61-2.mol

Synonyms:

Chemical Property of (3R,5S,1'S)-5-<1'--3'-methylbutyl>-3-(2-methylprop-2-enyl)dihydrofuran-2(3H)-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,5S,1'S)-5-<1'--3'-methylbutyl>-3-(2-methylprop-2-enyl)dihydrofuran-2(3H)-one

There total 8 articles about (3R,5S,1'S)-5-<1'--3'-methylbutyl>-3-(2-methylprop-2-enyl)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:

(3R,5S,1'S)-5-<1'--3'-methylbutyl>-3-(2-methylprop-2-enyl)dihydrofuran-2(3H)-one (172329-59-8) → (3R,5S,1'S)-5-<1'--3'-methylbutyl>-3-(2-methylprop-2-enyl)dihydrofuran-2(3H)-one (172329-61-2)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 0.166667h; Yield given; Ambient temperature;

DOI:10.1021/jo00129a037

Reference yield:

Methyl (4S,5S)-5--4-<(tert-butyldimethylsilyl)oxy>-6-phenylhexanoate (145655-06-7) → (3R,5S,1'S)-5-<1'--3'-methylbutyl>-3-(2-methylprop-2-enyl)dihydrofuran-2(3H)-one (172329-61-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) NiCl₂*6H₂O, NaBH₄, 2.) AcOH / 1.) MeOH, 0 deg C, 1 h; r.t., 18 h, 2.) toluene, reflux, 3 h

2: 75 percent / LHMDS / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) -78 to -40 deg C, 1.5 h

3: 5.2 M TFA / CH₂Cl₂ / 0.17 h / Ambient temperature

With sodium tetrahydroborate; acetic acid; trifluoroacetic acid; nickel dichloride; lithium hexamethyldisilazane; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo00129a037

Reference yield:

(1'R,2'S)-2-<2-(N-benzyl-N-tert-butoxycarbonylamino)-1-hydroxy-3-phenylpropyl>-1,3-thiazole (145655-01-2) → (3R,5S,1'S)-5-<1'--3'-methylbutyl>-3-(2-methylprop-2-enyl)dihydrofuran-2(3H)-one (172329-61-2)

Guidance literature:

Multi-step reaction with 8 steps

1: Et₃N, DMAP / dimethylformamide / 1 h / Ambient temperature

2: molecular sieves 4 Angstroem / acetonitrile / 0.25 h / Ambient temperature

3: 1.) NaBH₄, 2.) aq. HgCl₂ / 1.) MeOH, r.t., 10 min, 2.) CH₃CN, r.t., 15 min

4: toluene / 24 h / Ambient temperature

5: NiCl₂*6H₂O, NaBH₄ / methanol / 1.) 0 deg C, 1 h, 2.) r.t., 18 h

6: 1.) NiCl₂*6H₂O, NaBH₄, 2.) AcOH / 1.) MeOH, 0 deg C, 1 h; r.t., 18 h, 2.) toluene, reflux, 3 h

7: 75 percent / LHMDS / tetrahydrofuran; hexane / 1.) -78 deg C, 15 min, 2.) -78 to -40 deg C, 1.5 h

8: 5.2 M TFA / CH₂Cl₂ / 0.17 h / Ambient temperature

With dmap; sodium tetrahydroborate; 4 A molecular sieve; acetic acid; triethylamine; trifluoroacetic acid; mercury dichloride; nickel dichloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile;

DOI:10.1021/jo00129a037

upstream raw materials:

(3R,5S,1'S)-5-<1'--3'-methylbutyl>-3-(2-methylprop-2-enyl)dihydrofuran-2(3H)-one

(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

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