<<(2S,3R,5S,6R)-5-<(Benzyloxy)methoxy>-2-ethynyltetrahydro-2,6-dimethyl-6-(4-methyl-3-pentenyl)-2H-pyran-3-yl>oxy>trimethylsilane

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Chemical Name:<<(2S,3R,5S,6R)-5-<(Benzyloxy)methoxy>-2-ethynyltetrahydro-2,6-dimethyl-6-(4-methyl-3-pentenyl)-2H-pyran-3-yl>oxy>trimethylsilane
CAS No.:122624-98-0
Molecular Formula:C₂₆H₄₀O₄Si
Molecular Weight:444.687
Hs Code.:

Synonyms:<<(2S,3R,5S,6R)-5-<(Benzyloxy)methoxy>-2-ethynyltetrahydro-2,6-dimethyl-6-(4-methyl-3-pentenyl)-2H-pyran-3-yl>oxy>trimethylsilane

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Chemical Property of <<(2S,3R,5S,6R)-5-<(Benzyloxy)methoxy>-2-ethynyltetrahydro-2,6-dimethyl-6-(4-methyl-3-pentenyl)-2H-pyran-3-yl>oxy>trimethylsilane

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Technology Process of <<(2S,3R,5S,6R)-5-<(Benzyloxy)methoxy>-2-ethynyltetrahydro-2,6-dimethyl-6-(4-methyl-3-pentenyl)-2H-pyran-3-yl>oxy>trimethylsilane

There total 13 articles about <<(2S,3R,5S,6R)-5-<(Benzyloxy)methoxy>-2-ethynyltetrahydro-2,6-dimethyl-6-(4-methyl-3-pentenyl)-2H-pyran-3-yl>oxy>trimethylsilane 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%

: 122624-97-9
(2S,3R,6R)-5-<(Benzyloxy)methoxy>-2-<(Z)-2-chlorovinyl>-2,6-dimethyl-6-(4-methyl-3-pentenyl)-3-(trimethylsiloxy)tetrahydro-2H-pyran

: 122624-98-0
<<(2S,3R,5S,6R)-5-<(Benzyloxy)methoxy>-2-ethynyltetrahydro-2,6-dimethyl-6-(4-methyl-3-pentenyl)-2H-pyran-3-yl>oxy>trimethylsilane

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;
DOI:10.1021/ja00199a030

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 122624-98-0
<<(2S,3R,5S,6R)-5-<(Benzyloxy)methoxy>-2-ethynyltetrahydro-2,6-dimethyl-6-(4-methyl-3-pentenyl)-2H-pyran-3-yl>oxy>trimethylsilane

Guidance literature:: Multi-step reaction with 12 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

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; 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:

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

: 122624-98-0
<<(2S,3R,5S,6R)-5-<(Benzyloxy)methoxy>-2-ethynyltetrahydro-2,6-dimethyl-6-(4-methyl-3-pentenyl)-2H-pyran-3-yl>oxy>trimethylsilane

Guidance literature:: Multi-step reaction with 12 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

With titanium(IV) isopropylate; tert.-butylhydroperoxide; n-butyllithium; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; 4 A molecular sieve; tetrabutyl ammonium fluoride; 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