(S)-4-Benzyl-3-[(2S,3R,5S,7R,8R,9S)-3-hydroxy-7-methoxy-9-(4-methoxy-benzyloxy)-2-methoxymethoxy-10,10-dimethyl-5,8-bis-triethylsilanyloxy-dodec-11-enoyl]-oxazolidin-2-one

Base Information

Chemical Name:(S)-4-Benzyl-3-[(2S,3R,5S,7R,8R,9S)-3-hydroxy-7-methoxy-9-(4-methoxy-benzyloxy)-2-methoxymethoxy-10,10-dimethyl-5,8-bis-triethylsilanyloxy-dodec-11-enoyl]-oxazolidin-2-one
CAS No.:866089-60-3
Molecular Formula:C₄₇H₇₇NO₁₁Si₂
Molecular Weight:888.299
Hs Code.:

(S)-4-Benzyl-3-[(2S,3R,5S,7R,8R,9S)-3-hydroxy-7-methoxy-9-(4-methoxy-benzyloxy)-2-methoxymethoxy-10,10-dimethyl-5,8-bis-triethylsilanyloxy-dodec-11-enoyl]-oxazolidin-2-one

Synonyms:(S)-4-Benzyl-3-[(2S,3R,5S,7R,8R,9S)-3-hydroxy-7-methoxy-9-(4-methoxy-benzyloxy)-2-methoxymethoxy-10,10-dimethyl-5,8-bis-triethylsilanyloxy-dodec-11-enoyl]-oxazolidin-2-one

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Chemical Property of (S)-4-Benzyl-3-[(2S,3R,5S,7R,8R,9S)-3-hydroxy-7-methoxy-9-(4-methoxy-benzyloxy)-2-methoxymethoxy-10,10-dimethyl-5,8-bis-triethylsilanyloxy-dodec-11-enoyl]-oxazolidin-2-one

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Technology Process of (S)-4-Benzyl-3-[(2S,3R,5S,7R,8R,9S)-3-hydroxy-7-methoxy-9-(4-methoxy-benzyloxy)-2-methoxymethoxy-10,10-dimethyl-5,8-bis-triethylsilanyloxy-dodec-11-enoyl]-oxazolidin-2-one

There total 9 articles about (S)-4-Benzyl-3-[(2S,3R,5S,7R,8R,9S)-3-hydroxy-7-methoxy-9-(4-methoxy-benzyloxy)-2-methoxymethoxy-10,10-dimethyl-5,8-bis-triethylsilanyloxy-dodec-11-enoyl]-oxazolidin-2-one 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%

: (S)-4-Benzyl-3-(2-methoxymethoxy-acetyl)-oxazolidin-2-one

: 866089-58-9
(3R,5R,6R,7S)-5-Methoxy-7-(4-methoxy-benzyloxy)-8,8-dimethyl-3,6-bis-triethylsilanyloxy-dec-9-enal

: 866089-60-3
(S)-4-Benzyl-3-[(2S,3R,5S,7R,8R,9S)-3-hydroxy-7-methoxy-9-(4-methoxy-benzyloxy)-2-methoxymethoxy-10,10-dimethyl-5,8-bis-triethylsilanyloxy-dodec-11-enoyl]-oxazolidin-2-one

Guidance literature:: (S)-4-Benzyl-3-(2-methoxymethoxy-acetyl)-oxazolidin-2-one; With di-n-butylboryl trifluoromethanesulfonate; triethylamine; In dichloromethane; at -78 - 0 ℃;

(3R,5R,6R,7S)-5-Methoxy-7-(4-methoxy-benzyloxy)-8,8-dimethyl-3,6-bis-triethylsilanyloxy-dec-9-enal; In dichloromethane; at -78 - 0 ℃;
DOI:10.1021/ol0514303

Reference yield:

: 236110-81-9
(4S)-4-benzyl-3-[2-(benzyloxy)acetyl]-1,3-oxazolan-2-one

: 866089-60-3
(S)-4-Benzyl-3-[(2S,3R,5S,7R,8R,9S)-3-hydroxy-7-methoxy-9-(4-methoxy-benzyloxy)-2-methoxymethoxy-10,10-dimethyl-5,8-bis-triethylsilanyloxy-dodec-11-enoyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: hydrogen / Pd(OH)2/C / ethyl acetate / 3.5 h

1.2: 67 percent / Bu₄NI; DIPEA / CH₂Cl₂ / 18 h

2.1: Et₃N; dibutylboron triflate / CH₂Cl₂ / -78 - 0 °C

2.2: 86 percent / CH₂Cl₂ / -78 - 0 °C

With di-n-butylboryl trifluoromethanesulfonate; hydrogen; triethylamine; palladium dihydroxide; In dichloromethane; ethyl acetate;
DOI:10.1021/ol0514303

Reference yield:

: (4S,5R)-5-((1R,3S)-5-Benzyloxy-1-methoxy-3-triethylsilanyloxy-pentyl)-4-(4-methoxy-benzyloxy)-3,3-dimethyl-tetrahydro-furan-2-ol

: 866089-60-3
(S)-4-Benzyl-3-[(2S,3R,5S,7R,8R,9S)-3-hydroxy-7-methoxy-9-(4-methoxy-benzyloxy)-2-methoxymethoxy-10,10-dimethyl-5,8-bis-triethylsilanyloxy-dodec-11-enoyl]-oxazolidin-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 - 20 °C

1.2: tetrahydrofuran; hexane / 16.5 h / 65 °C

2.1: 82 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 °C

3.1: 91 percent / 4,4'-di-tert-butylbiphenyl; lithium / tetrahydrofuran / 2 h / -78 °C

4.1: 95 percent / pyridine; Dess-Martin periodinane / CH₂Cl₂ / 0 - 20 °C

5.1: Et₃N; dibutylboron triflate / CH₂Cl₂ / -78 - 0 °C

5.2: 86 percent / CH₂Cl₂ / -78 - 0 °C

With pyridine; 2,6-dimethylpyridine; n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; 4,4'-di-tert-butylbiphenyl; lithium; Dess-Martin periodane; triethylamine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1021/ol0514303