(4S,5R)-4-<(Benzyloxy)methoxy>dihydro-5-methyl-5-(4-methyl-3-pentenyl)-2(3H)-furanone

Base Information

Chemical Name:(4S,5R)-4-<(Benzyloxy)methoxy>dihydro-5-methyl-5-(4-methyl-3-pentenyl)-2(3H)-furanone
CAS No.:122624-86-6
Molecular Formula:C₁₉H₂₆O₄
Molecular Weight:318.413
Hs Code.:

Synonyms:(4S,5R)-4-<(Benzyloxy)methoxy>dihydro-5-methyl-5-(4-methyl-3-pentenyl)-2(3H)-furanone

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Chemical Property of (4S,5R)-4-<(Benzyloxy)methoxy>dihydro-5-methyl-5-(4-methyl-3-pentenyl)-2(3H)-furanone

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Technology Process of (4S,5R)-4-<(Benzyloxy)methoxy>dihydro-5-methyl-5-(4-methyl-3-pentenyl)-2(3H)-furanone

There total 1 articles about (4S,5R)-4-<(Benzyloxy)methoxy>dihydro-5-methyl-5-(4-methyl-3-pentenyl)-2(3H)-furanone 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: 84.0%

: 3587-60-8
Benzyloxymethyl chloride

: 122624-85-5
(4S,5R)-5-(4'-methyl-3'-pentenyl)-4-hydroxy-5-methyldihydrofuran-2-one

: 122624-86-6
(4S,5R)-4-<(Benzyloxy)methoxy>dihydro-5-methyl-5-(4-methyl-3-pentenyl)-2(3H)-furanone

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In 1,2-dichloro-ethane; at 75 ℃; for 18h;
DOI:10.1021/ja00199a030

Reference yield:

: 122624-86-6
(4S,5R)-4-<(Benzyloxy)methoxy>dihydro-5-methyl-5-(4-methyl-3-pentenyl)-2(3H)-furanone

: 122625-05-2
(2S,3R,5S,6R)-5-<(Benzyloxy)methoxy>-3-<(2R,3R)-2,3-epoxy-3-methyl-4-pentenyl>tetrahydro-2,6-dimethyl-6-(4-methyl-3-pentenyl)-2H-pyran-3-ol

Guidance literature:: Multi-step reaction with 18 steps

1: 100 percent / DIBAL / CH₂Cl₂; hexane / 0.75 h / -78 °C

2: 82 percent / benzene / 18 h / 70 °C

3: 100 percent / 1,2-dichloro-ethane / 6 h / 60 °C

4: 100 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C

5: 1.) 4A molecular sieves, D-(-)-diethyl tartrate, Ti(O-iPr)4, 2.) t-BuOOH / 1.) CH₂Cl₂, -40 deg C, 30 min, 2.) -20 deg C, 16 h

6: SO₃-pyr, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

7: 79 percent / NaN(SiMe₃)2 / tetrahydrofuran / 0.5 h / 0 °C

8: 96 percent / n-Bu₄NF / tetrahydrofuran / 1.5 h / Ambient temperature

9: 83 percent / (1S)-(+)-10-camphorsulfonic acid / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) 1.5 h

10: 100 percent / CH₂Cl₂ / 2 h / 25 °C

11: 86 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

12: 1.) BH₃e*THF, 2-methyl-2-butene, 2.) aq. NaOH, aq. H₂O₂ / 1.) THF, 0 deg C, 45 min; r.t., 20 min, 2.) 0 deg C, 20 min

13: 75 percent / benzene / 3 h / 25 °C

14: 100 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

15: 1.) 4A molecular sieves, D-(-)-diethyl tartrate, Ti(O-iPr)4, 2.) t-BuOOH / 1.) CH₂Cl₂, -40 deg C, 30 min, 2.) -20 deg C, 16 h

16: 90 percent / SO₃-pyr, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 4 h / 0 °C

17: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, 0 deg C, 30 min, 2.) 0 deg C, 30 min

18: 97 percent / n-Bu₄NF / tetrahydrofuran / 3 h / 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; n-butyllithium; borane-THF; 2-methyl-but-2-ene; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; (+)-10-camphorsulfonic acid; triethylamine; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; benzene;
DOI:10.1021/ja00199a030

Reference yield:

: 122624-86-6
(4S,5R)-4-<(Benzyloxy)methoxy>dihydro-5-methyl-5-(4-methyl-3-pentenyl)-2(3H)-furanone

: 122624-93-5
(1Z,3S,4R,6S,7R)-6-<(Benzyloxy)methoxy>-1-chloro-3,4-epoxy-3,7,11-trimethyl-7-(trimethylsiloxy)-1,10-dodecadiene

Guidance literature:: Multi-step reaction with 7 steps

1: 100 percent / DIBAL / CH₂Cl₂; hexane / 0.75 h / -78 °C

2: 82 percent / benzene / 18 h / 70 °C

3: 100 percent / 1,2-dichloro-ethane / 6 h / 60 °C

4: 100 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C

5: 1.) 4A molecular sieves, D-(-)-diethyl tartrate, Ti(O-iPr)4, 2.) t-BuOOH / 1.) CH₂Cl₂, -40 deg C, 30 min, 2.) -20 deg C, 16 h

6: SO₃-pyr, Et₃N / dimethylsulfoxide; CH₂Cl₂ / 2 h / 0 °C

7: 79 percent / NaN(SiMe₃)2 / tetrahydrofuran / 0.5 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; 4 A molecular sieve; sodium hexamethyldisilazane; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; benzene;
DOI:10.1021/ja00199a030