4-<(2S,3R,5S,6R)-5-<(Benzyloxy)methoxy>-2,6-dimethyl-6-(4-methyl-3-pentenyl)-3-(trimethylsiloxy)tetrahydro-2H-pyran-2-yl>-(2E)-crotyl alcohol

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Chemical Name:4-<(2S,3R,5S,6R)-5-<(Benzyloxy)methoxy>-2,6-dimethyl-6-(4-methyl-3-pentenyl)-3-(trimethylsiloxy)tetrahydro-2H-pyran-2-yl>-(2E)-crotyl alcohol
CAS No.:122625-01-8
Molecular Formula:C₂₉H₄₈O₅Si
Molecular Weight:504.783
Hs Code.:

Synonyms:4-<(2S,3R,5S,6R)-5-<(Benzyloxy)methoxy>-2,6-dimethyl-6-(4-methyl-3-pentenyl)-3-(trimethylsiloxy)tetrahydro-2H-pyran-2-yl>-(2E)-crotyl alcohol

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Chemical Property of 4-<(2S,3R,5S,6R)-5-<(Benzyloxy)methoxy>-2,6-dimethyl-6-(4-methyl-3-pentenyl)-3-(trimethylsiloxy)tetrahydro-2H-pyran-2-yl>-(2E)-crotyl alcohol

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Technology Process of 4-<(2S,3R,5S,6R)-5-<(Benzyloxy)methoxy>-2,6-dimethyl-6-(4-methyl-3-pentenyl)-3-(trimethylsiloxy)tetrahydro-2H-pyran-2-yl>-(2E)-crotyl alcohol

There total 14 articles about 4-<(2S,3R,5S,6R)-5-<(Benzyloxy)methoxy>-2,6-dimethyl-6-(4-methyl-3-pentenyl)-3-(trimethylsiloxy)tetrahydro-2H-pyran-2-yl>-(2E)-crotyl alcohol 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:

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

: 122625-01-8
4-<(2S,3R,5S,6R)-5-<(Benzyloxy)methoxy>-2,6-dimethyl-6-(4-methyl-3-pentenyl)-3-(trimethylsiloxy)tetrahydro-2H-pyran-2-yl>-(2E)-crotyl alcohol

Guidance literature:: Multi-step reaction with 15 steps

1: 84 percent / NEt(i-Pr)2 / 1,2-dichloro-ethane / 18 h / 75 °C

2: 100 percent / DIBAL / CH₂Cl₂; hexane / 0.75 h / -78 °C

3: 82 percent / benzene / 18 h / 70 °C

4: 100 percent / 1,2-dichloro-ethane / 6 h / 60 °C

5: 100 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C

6: 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

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

8: 79 percent / NaN(SiMe₃)2 / tetrahydrofuran / 0.5 h / 0 °C

9: 96 percent / n-Bu₄NF / tetrahydrofuran / 1.5 h / Ambient temperature

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

11: 100 percent / CH₂Cl₂ / 2 h / 25 °C

12: 86 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

13: 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

14: 75 percent / benzene / 3 h / 25 °C

15: 100 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °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; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; hexane; dichloromethane; dimethyl sulfoxide; 1,2-dichloro-ethane; benzene;
DOI:10.1021/ja00199a030

Reference yield:

: 122624-87-7,122624-88-8
(4S,5R)-4-<(Benzyloxy)methoxy>-2-hydroxy-5-methyl-5-(4-methyl-3-pentenyl)tetrahydrofuran

: 122625-01-8
4-<(2S,3R,5S,6R)-5-<(Benzyloxy)methoxy>-2,6-dimethyl-6-(4-methyl-3-pentenyl)-3-(trimethylsiloxy)tetrahydro-2H-pyran-2-yl>-(2E)-crotyl alcohol

Guidance literature:: Multi-step reaction with 13 steps

1: 82 percent / benzene / 18 h / 70 °C

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

3: 100 percent / DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C

4: 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

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

6: 79 percent / NaN(SiMe₃)2 / tetrahydrofuran / 0.5 h / 0 °C

7: 96 percent / n-Bu₄NF / tetrahydrofuran / 1.5 h / Ambient temperature

8: 83 percent / (1S)-(+)-10-camphorsulfonic acid / CH₂Cl₂ / 1.) 0 deg C, 1 h, 2.) 1.5 h

9: 100 percent / CH₂Cl₂ / 2 h / 25 °C

10: 86 percent / n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

11: 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

12: 75 percent / benzene / 3 h / 25 °C

13: 100 percent / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °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

: 122625-01-8
4-<(2S,3R,5S,6R)-5-<(Benzyloxy)methoxy>-2,6-dimethyl-6-(4-methyl-3-pentenyl)-3-(trimethylsiloxy)tetrahydro-2H-pyran-2-yl>-(2E)-crotyl alcohol

Guidance literature:: Multi-step reaction with 14 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

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