((2S,3R,6S)-6-((1S,4S,5S)-1,4-bis(benzyloxy)-5-(triethylsilyloxy)hept-6-enyl)-2-decyl-3,6-dihydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane

Base Information

Chemical Name:((2S,3R,6S)-6-((1S,4S,5S)-1,4-bis(benzyloxy)-5-(triethylsilyloxy)hept-6-enyl)-2-decyl-3,6-dihydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane
CAS No.:1335101-56-8
Molecular Formula:C₄₈H₈₀O₅Si₂
Molecular Weight:793.331
Hs Code.:

Synonyms:((2S,3R,6S)-6-((1S,4S,5S)-1,4-bis(benzyloxy)-5-(triethylsilyloxy)hept-6-enyl)-2-decyl-3,6-dihydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of ((2S,3R,6S)-6-((1S,4S,5S)-1,4-bis(benzyloxy)-5-(triethylsilyloxy)hept-6-enyl)-2-decyl-3,6-dihydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

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Technology Process of ((2S,3R,6S)-6-((1S,4S,5S)-1,4-bis(benzyloxy)-5-(triethylsilyloxy)hept-6-enyl)-2-decyl-3,6-dihydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane

There total 23 articles about ((2S,3R,6S)-6-((1S,4S,5S)-1,4-bis(benzyloxy)-5-(triethylsilyloxy)hept-6-enyl)-2-decyl-3,6-dihydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane 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: 85.0%

: 1335101-55-7
(2S,3R,6S)-6-((1S,4S,5S)-1,4-bis(benzyloxy)-5-(triethylsilyloxy)hept-6-enyl)-2-decyl-3,6-dihydro-2H-pyran-3-ol

: 69739-34-0
t-butyldimethylsiyl triflate

: 1335101-56-8
((2S,3R,6S)-6-((1S,4S,5S)-1,4-bis(benzyloxy)-5-(triethylsilyloxy)hept-6-enyl)-2-decyl-3,6-dihydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at -78 ℃; for 0.25h; Inert atmosphere;
DOI:10.1016/j.tet.2011.07.079

Reference yield:

: 1335101-40-0
(S,3E,5E)-1-((S)-p-tolylsulfinyl)hepta-3,5-dien-2-ol

: 1335101-56-8
((2S,3R,6S)-6-((1S,4S,5S)-1,4-bis(benzyloxy)-5-(triethylsilyloxy)hept-6-enyl)-2-decyl-3,6-dihydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane

Guidance literature:: Multi-step reaction with 16 steps

1.1: 1H-imidazole / dichloromethane / 0 - 20 °C / Inert atmosphere

2.1: water / toluene / 0.08 h / 20 °C

2.2: 2 h / 20 °C

3.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

4.1: camphor-10-sulfonic acid / dichloromethane / 4 h / Inert atmosphere

5.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 96 h / Inert atmosphere; Reflux

6.1: platinum oxide on carbon; hydrogen / methanol; benzene / 24 h / 20 °C / 7500.75 Torr / Inert atmosphere

7.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

8.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 0 - 20 °C / Inert atmosphere

9.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.58 h / 0 - 20 °C / Inert atmosphere

10.1: ethanol; magnesium; mercury dichloride / 4 h / 0 - 20 °C / Inert atmosphere

11.1: boron trifluoride diethyl etherate / dichloromethane / 39 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

11.2: 0.17 h / Cooling with ice

12.1: ethanol; potassium carbonate / acetonitrile / 12 h / 20 °C / Inert atmosphere

13.1: 1H-imidazole / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

14.1: n-butyllithium / tetrahydrofuran; hexanes / 1 h / -10 °C / Inert atmosphere

14.2: 4 h / -10 - 20 °C / Inert atmosphere

15.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 12 h / Reflux

16.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / -78 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; n-butyllithium; Hoveyda-Grubbs catalyst second generation; ethanol; trifluorormethanesulfonic acid; platinum oxide on carbon; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; potassium carbonate; magnesium; acetic acid; 3-chloro-benzenecarboperoxoic acid; mercury dichloride; In tetrahydrofuran; methanol; hexanes; dichloromethane; cyclohexane; toluene; acetonitrile; benzene;
DOI:10.1016/j.tet.2011.07.079

Reference yield:

: 1335101-42-2
tert-butyldimethyl((2S,3E,5E)-(1Ss)-(p-tolylsulfinyl)hepta-3,5-dien-2-yloxy)silane

: 1335101-56-8
((2S,3R,6S)-6-((1S,4S,5S)-1,4-bis(benzyloxy)-5-(triethylsilyloxy)hept-6-enyl)-2-decyl-3,6-dihydro-2H-pyran-3-yloxy)(tert-butyl)dimethylsilane

Guidance literature:: Multi-step reaction with 15 steps

1.1: water / toluene / 0.08 h / 20 °C

1.2: 2 h / 20 °C

2.1: tetrabutyl ammonium fluoride; acetic acid / tetrahydrofuran / 12 h / 20 °C / Inert atmosphere

3.1: camphor-10-sulfonic acid / dichloromethane / 4 h / Inert atmosphere

4.1: Hoveyda-Grubbs catalyst second generation / dichloromethane / 96 h / Inert atmosphere; Reflux

5.1: platinum oxide on carbon; hydrogen / methanol; benzene / 24 h / 20 °C / 7500.75 Torr / Inert atmosphere

6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.33 h / 0 °C / Inert atmosphere

7.1: trifluorormethanesulfonic acid / dichloromethane; cyclohexane / 0 - 20 °C / Inert atmosphere

8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.58 h / 0 - 20 °C / Inert atmosphere

9.1: ethanol; magnesium; mercury dichloride / 4 h / 0 - 20 °C / Inert atmosphere

10.1: boron trifluoride diethyl etherate / dichloromethane / 39 h / 0 - 20 °C / Inert atmosphere; Molecular sieve

10.2: 0.17 h / Cooling with ice

11.1: ethanol; potassium carbonate / acetonitrile / 12 h / 20 °C / Inert atmosphere

12.1: 1H-imidazole / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere

13.1: n-butyllithium / tetrahydrofuran; hexanes / 1 h / -10 °C / Inert atmosphere

13.2: 4 h / -10 - 20 °C / Inert atmosphere

14.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 12 h / Reflux

15.1: 2,6-dimethylpyridine / dichloromethane / 0.25 h / -78 °C / Inert atmosphere

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; 2,6-dimethylpyridine; n-butyllithium; Hoveyda-Grubbs catalyst second generation; ethanol; trifluorormethanesulfonic acid; platinum oxide on carbon; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; potassium carbonate; magnesium; acetic acid; 3-chloro-benzenecarboperoxoic acid; mercury dichloride; In tetrahydrofuran; methanol; hexanes; dichloromethane; cyclohexane; toluene; acetonitrile; benzene;
DOI:10.1016/j.tet.2011.07.079