methyl 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)acetate

Base Information

• Chemical Name: methyl 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)acetate
• CAS No.: 949148-94-1
• Molecular Formula: C₄₂H₆₂O₅Si
• Molecular Weight: 675.037
• Mol file: 949148-94-1.mol

Synonyms:methyl 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)acetate

Chemical Property of methyl 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)acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 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)acetate

There total 19 articles about methyl 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)acetate 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:

(E)-(S)-3-(dimethyl-phenyl-silanyl)-3-methyl-hex-4-enoic acid methyl ester (949148-84-9) → methyl 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)acetate (949148-94-1)

Guidance literature:

Multi-step reaction with 13 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

11.1: diisobutylaluminium hydride / CH₂Cl₂; hexane / 3 h / -78 - 0 °C

12.1: 2-methyl-1-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 3 h / 20 °C

13.1: 17 mg / benzene; methanol; hexane / 0.25 h / 20 °C

With chromium dichloride; lithium hydroxide; sodium chlorite; sodium dihydrogenphosphate; borane-ammonia complex; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; silver benzoate; diisobutylaluminium hydride; 2-Methyl-1-butene; 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; tert-butyl alcohol; benzene; 8.1: Swern oxidation / 9.1: Takai olefination;

DOI:10.1021/ol701427k

Reference yield:

(2S,6S,7R,8S,E)-8-(tert-butyldiphenylsilyloxy)-7-methoxy-2,4,6-trimethylnon-4-en-1-ol (949148-89-4) → methyl 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)acetate (949148-94-1)

Guidance literature:

Multi-step reaction with 6 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

4: diisobutylaluminium hydride / CH₂Cl₂; hexane / 3 h / -78 - 0 °C

5: 2-methyl-1-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 3 h / 20 °C

6: 17 mg / benzene; methanol; hexane / 0.25 h / 20 °C

With chromium dichloride; sodium chlorite; sodium dihydrogenphosphate; oxalyl dichloride; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; 2-Methyl-1-butene; dimethyl sulfoxide; triethylamine; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; water; tert-butyl alcohol; benzene; 1: Swern oxidation / 2: Takai olefination;

DOI:10.1021/ol701427k

Reference yield:

tert-butyl((2S,3R,4S,5E,8S,9E)-10-iodo-3-methoxy-4,6,8-trimethyldeca-5,9-dien-2-yloxy)diphenylsilane (949148-81-6) → methyl 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)acetate (949148-94-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 71 percent / tetrabutylammonium fluoride / allylpalladium chloride dimer / tetrahydrofuran / 6 h / 20 °C

2: diisobutylaluminium hydride / CH₂Cl₂; hexane / 3 h / -78 - 0 °C

3: 2-methyl-1-butene; NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 3 h / 20 °C

4: 17 mg / benzene; methanol; hexane / 0.25 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; 2-Methyl-1-butene; bis(η3-allyl-μ-chloropalladium(II)); In tetrahydrofuran; methanol; hexane; dichloromethane; water; tert-butyl alcohol; benzene;

DOI:10.1021/ol701427k

upstream raw materials:

diazomethyl-trimethyl-silane

(E)-(S)-3-(dimethyl-phenyl-silanyl)-3-methyl-hex-4-enoic acid methyl ester

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

C₂₉H₄₂O₃Si

Downstream raw materials:

2-((2R,5S,6S)-6-((S,2E,4E)-7-((2R,3R)-3-((2R,3R,4R)-4-hydroxy-3-methoxypentan-2-yl)-2-methyloxiran-2-yl)-6-methylhepta-2,4-dien-2-yl)-5-methyltetrahydro-2H-pyran-2-yl)acetic acid