(E)-(2R,3S,4S,6R,7R,10S,11R)-2-(tert-Butyl-dimethyl-silanyloxy)-11-(3,4-dimethoxy-benzyloxy)-7-hydroxy-3-methoxy-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid allyl ester

Base Information

• Chemical Name: (E)-(2R,3S,4S,6R,7R,10S,11R)-2-(tert-Butyl-dimethyl-silanyloxy)-11-(3,4-dimethoxy-benzyloxy)-7-hydroxy-3-methoxy-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid allyl ester
• CAS No.: 852952-74-0
• Molecular Formula: C₃₅H₅₈O₉Si
• Molecular Weight: 650.926
• Mol file: 852952-74-0.mol

Synonyms:(E)-(2R,3S,4S,6R,7R,10S,11R)-2-(tert-Butyl-dimethyl-silanyloxy)-11-(3,4-dimethoxy-benzyloxy)-7-hydroxy-3-methoxy-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid allyl ester

Chemical Property of (E)-(2R,3S,4S,6R,7R,10S,11R)-2-(tert-Butyl-dimethyl-silanyloxy)-11-(3,4-dimethoxy-benzyloxy)-7-hydroxy-3-methoxy-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid allyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(2R,3S,4S,6R,7R,10S,11R)-2-(tert-Butyl-dimethyl-silanyloxy)-11-(3,4-dimethoxy-benzyloxy)-7-hydroxy-3-methoxy-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid allyl ester

There total 6 articles about (E)-(2R,3S,4S,6R,7R,10S,11R)-2-(tert-Butyl-dimethyl-silanyloxy)-11-(3,4-dimethoxy-benzyloxy)-7-hydroxy-3-methoxy-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid allyl ester 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:

(2R,3S,4S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-4-methyl-5-oxo-heptanoic acid allyl ester (852952-73-9) + (2E,4S,5R)-5-(3,4-dimethoxybenzyloxy)-2,4-dimethyl-hex-2-enal (488099-58-7) → (E)-(2R,3S,4S,6R,7S,10S,11R)-2-(tert-Butyl-dimethyl-silanyloxy)-11-(3,4-dimethoxy-benzyloxy)-7-hydroxy-3-methoxy-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid allyl ester + (E)-(2R,3S,4S,6R,7R,10S,11R)-2-(tert-Butyl-dimethyl-silanyloxy)-11-(3,4-dimethoxy-benzyloxy)-7-hydroxy-3-methoxy-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid allyl ester (852952-74-0)

Guidance literature:

(2R,3S,4S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-4-methyl-5-oxo-heptanoic acid allyl ester; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 0.133333h;

(2E,4S,5R)-5-(3,4-dimethoxybenzyloxy)-2,4-dimethyl-hex-2-enal; In dichloromethane; at -78 - 0 ℃;

DOI:10.1021/ja050729d

Reference yield:

(2R,3S,4S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-4-methyl-5-oxo-heptanoic acid allyl ester (852952-73-9) + (2E,4S,5R)-5-(3,4-dimethoxybenzyloxy)-2,4-dimethyl-hex-2-enal (488099-58-7) → (E)-(2R,3S,4S,6R,7S,10S,11R)-2-(tert-Butyl-dimethyl-silanyloxy)-11-(3,4-dimethoxy-benzyloxy)-7-hydroxy-3-methoxy-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid allyl ester + (E)-(2R,3S,4S,6R,7R,10S,11R)-2-(tert-Butyl-dimethyl-silanyloxy)-11-(3,4-dimethoxy-benzyloxy)-7-hydroxy-3-methoxy-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid allyl ester (852952-74-0) + C15H28O4Si

Guidance literature:

(2R,3S,4S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-4-methyl-5-oxo-heptanoic acid allyl ester; With titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 ℃; for 0.133333h; Molecular sieve;

(2E,4S,5R)-5-(3,4-dimethoxybenzyloxy)-2,4-dimethyl-hex-2-enal; In dichloromethane; at -78 - 0 ℃; optical yield given as %de;

DOI:10.1021/ja8063205

Reference yield:

(2R,3S,4R,5R)-2-(tert-Butyl-dimethyl-silanyloxy)-5-hydroxy-3-methoxy-4-methyl-heptanoic acid allyl ester → (E)-(2R,3S,4S,6R,7R,10S,11R)-2-(tert-Butyl-dimethyl-silanyloxy)-11-(3,4-dimethoxy-benzyloxy)-7-hydroxy-3-methoxy-4,6,8,10-tetramethyl-5-oxo-dodec-8-enoic acid allyl ester (852952-74-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: TPAP; NMO

2.1: TiCl₄; i-Pr₂NEt / CH₂Cl₂ / 0.13 h / -78 °C

2.2: CH₂Cl₂ / -78 - 0 °C

With N-methyl-2-indolinone; tetrapropylammonium perruthennate; titanium tetrachloride; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1021/ja050729d

upstream raw materials:

(2R,3S,4S)-2-(tert-Butyl-dimethyl-silanyloxy)-3-methoxy-4-methyl-5-oxo-heptanoic acid allyl ester

(2E,4S,5R)-5-(3,4-dimethoxybenzyloxy)-2,4-dimethyl-hex-2-enal

(2R,3S,4S,5R)-5-[(3,4-dimethoxybenzyl)oxy]-3-methoxy-4-methyl-2-[(tert-butyldimethylsilyl)oxy]heptanal