2-((2R,5S,6S)-6-((2E,4E,6S,8E,10S,11R,12S)-12-(tert-butyldiphenylsilyloxy)-11-methoxy-6,8,10-trimethyltrideca-2,4,8-trien-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)acetonitrile

Base Information

Chemical Name:2-((2R,5S,6S)-6-((2E,4E,6S,8E,10S,11R,12S)-12-(tert-butyldiphenylsilyloxy)-11-methoxy-6,8,10-trimethyltrideca-2,4,8-trien-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)acetonitrile
CAS No.:949148-93-0
Molecular Formula:C₄₁H₅₉NO₃Si
Molecular Weight:642.01
Hs Code.:

2-((2R,5S,6S)-6-((2E,4E,6S,8E,10S,11R,12S)-12-(tert-butyldiphenylsilyloxy)-11-methoxy-6,8,10-trimethyltrideca-2,4,8-trien-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)acetonitrile

Synonyms:2-((2R,5S,6S)-6-((2E,4E,6S,8E,10S,11R,12S)-12-(tert-butyldiphenylsilyloxy)-11-methoxy-6,8,10-trimethyltrideca-2,4,8-trien-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)acetonitrile

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Chemical Property of 2-((2R,5S,6S)-6-((2E,4E,6S,8E,10S,11R,12S)-12-(tert-butyldiphenylsilyloxy)-11-methoxy-6,8,10-trimethyltrideca-2,4,8-trien-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)acetonitrile

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Technology Process of 2-((2R,5S,6S)-6-((2E,4E,6S,8E,10S,11R,12S)-12-(tert-butyldiphenylsilyloxy)-11-methoxy-6,8,10-trimethyltrideca-2,4,8-trien-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)acetonitrile

There total 15 articles about 2-((2R,5S,6S)-6-((2E,4E,6S,8E,10S,11R,12S)-12-(tert-butyldiphenylsilyloxy)-11-methoxy-6,8,10-trimethyltrideca-2,4,8-trien-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)acetonitrile 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: 71.0%

: 949148-81-6
tert-butyl((2S,3R,4S,5E,8S,9E)-10-iodo-3-methoxy-4,6,8-trimethyldeca-5,9-dien-2-yloxy)diphenylsilane

: 949148-92-9
2-((2R,5S,6S)-6-((E)-1-(benzyldimethylsilyl)prop-1-en-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)acetonitrile

: 949148-93-0
2-((2R,5S,6S)-6-((2E,4E,6S,8E,10S,11R,12S)-12-(tert-butyldiphenylsilyloxy)-11-methoxy-6,8,10-trimethyltrideca-2,4,8-trien-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)acetonitrile

Guidance literature:: With tetrabutyl ammonium fluoride; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; at 20 ℃; for 6h;
DOI:10.1021/ol701427k

Reference yield:

: 949148-84-9
(E)-(S)-3-(dimethyl-phenyl-silanyl)-3-methyl-hex-4-enoic acid methyl ester

: 949148-93-0
2-((2R,5S,6S)-6-((2E,4E,6S,8E,10S,11R,12S)-12-(tert-butyldiphenylsilyloxy)-11-methoxy-6,8,10-trimethyltrideca-2,4,8-trien-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)acetonitrile

Guidance literature:: Multi-step reaction with 10 steps

1.1: 62 percent / trimethylsilyl trifluoromethanesulfonate / CH₂Cl₂ / 24 h / -50 °C

2.1: LiOH / tetrahydrofuran; methanol; H₂O / 3 h / 20 °C

3.1: oxalyl chloride / CH₂Cl₂; dimethylformamide / 20 °C

4.1: 1.68 g / diethyl ether / 0.5 h / 0 °C

5.1: 80 percent / silver benzoate / CH₂Cl₂ / 0.08 h / 20 °C

6.1: lithium diisopropylamide / tetrahydrofuran; hexane / 1.75 h / -78 - 0 °C

6.2: tetrahydrofuran; hexane / 0.5 h / 0 °C

7.1: lithium diisopropylamide; BH₃*NH₃ / tetrahydrofuran; hexane / 2 h / 20 °C

8.1: 100 percent / oxalyl chloride; methyl sulfoxide; triethylamine / CH₂Cl₂

9.1: 381 mg / CrCl₂ / dioxane; tetrahydrofuran / 0 - 20 °C

10.1: 71 percent / tetrabutylammonium fluoride / allylpalladium chloride dimer / tetrahydrofuran / 6 h / 20 °C

With chromium dichloride; lithium hydroxide; borane-ammonia complex; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; silver benzoate; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; 8.1: Swern oxidation / 9.1: Takai olefination;
DOI:10.1021/ol701427k

Reference yield:

: 949148-89-4
(2S,6S,7R,8S,E)-8-(tert-butyldiphenylsilyloxy)-7-methoxy-2,4,6-trimethylnon-4-en-1-ol

: 949148-93-0
2-((2R,5S,6S)-6-((2E,4E,6S,8E,10S,11R,12S)-12-(tert-butyldiphenylsilyloxy)-11-methoxy-6,8,10-trimethyltrideca-2,4,8-trien-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)acetonitrile

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / oxalyl chloride; methyl sulfoxide; triethylamine / CH₂Cl₂

2: 381 mg / CrCl₂ / dioxane; tetrahydrofuran / 0 - 20 °C

3: 71 percent / tetrabutylammonium fluoride / allylpalladium chloride dimer / tetrahydrofuran / 6 h / 20 °C

With chromium dichloride; oxalyl dichloride; tetrabutyl ammonium fluoride; dimethyl sulfoxide; triethylamine; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; 1,4-dioxane; dichloromethane; 1: Swern oxidation / 2: Takai olefination;
DOI:10.1021/ol701427k