(5S,6S,7S,8S)-5-Hydroxy-7-(4-methoxy-benzyloxy)-4,4,6,8-tetramethyl-3-oxo-undec-10-enoic acid tert-butyl ester

Base Information

Chemical Name:(5S,6S,7S,8S)-5-Hydroxy-7-(4-methoxy-benzyloxy)-4,4,6,8-tetramethyl-3-oxo-undec-10-enoic acid tert-butyl ester
CAS No.:461044-32-6
Molecular Formula:C₂₇H₄₂O₆
Molecular Weight:462.627
Hs Code.:

Synonyms:(5S,6S,7S,8S)-5-Hydroxy-7-(4-methoxy-benzyloxy)-4,4,6,8-tetramethyl-3-oxo-undec-10-enoic acid tert-butyl ester

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Chemical Property of (5S,6S,7S,8S)-5-Hydroxy-7-(4-methoxy-benzyloxy)-4,4,6,8-tetramethyl-3-oxo-undec-10-enoic acid tert-butyl ester

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Technology Process of (5S,6S,7S,8S)-5-Hydroxy-7-(4-methoxy-benzyloxy)-4,4,6,8-tetramethyl-3-oxo-undec-10-enoic acid tert-butyl ester

There total 11 articles about (5S,6S,7S,8S)-5-Hydroxy-7-(4-methoxy-benzyloxy)-4,4,6,8-tetramethyl-3-oxo-undec-10-enoic acid tert-butyl 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: 70.0%

: 94250-54-1
tert-butyl 4-methyl-3-oxopentanoate

: 461044-31-5
(2R,3S,4S)-3-(4-Methoxy-benzyloxy)-2,4-dimethyl-hept-6-enal

: 461044-32-6
(5S,6S,7S,8S)-5-Hydroxy-7-(4-methoxy-benzyloxy)-4,4,6,8-tetramethyl-3-oxo-undec-10-enoic acid tert-butyl ester

Guidance literature:: With n-butyllithium; sodium hydride; at 0 ℃;
DOI:10.1002/1521-3773(20020415)41:8<1404::AID-ANIE1404>3.0.CO;2-G

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 461044-32-6
(5S,6S,7S,8S)-5-Hydroxy-7-(4-methoxy-benzyloxy)-4,4,6,8-tetramethyl-3-oxo-undec-10-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / 10-camphorsulfonic acid

2: 90 percent / LiAlH₄ / 0 - 20 °C

3: 94 percent / triethylamine

4: 88 percent / LiAlH₄

5: 93 percent / diisobutylaluminium hydride / toluene

6: 70 percent / NaH; n-BuLi / 0 °C

With lithium aluminium tetrahydride; n-butyllithium; (1S)-10-camphorsulfonic acid; sodium hydride; diisobutylaluminium hydride; triethylamine; In toluene; 6: Dess-Martin oxidation;
DOI:10.1002/1521-3773(20020415)41:8<1404::AID-ANIE1404>3.0.CO;2-G

Reference yield:

: 461044-22-4
(4S,5S)-4-Hydroxy-5-methyl-tetrahydro-pyran-2-one

: 461044-32-6
(5S,6S,7S,8S)-5-Hydroxy-7-(4-methoxy-benzyloxy)-4,4,6,8-tetramethyl-3-oxo-undec-10-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 85 percent / lithium diisopropylamide / hexamethylphosphoric acid triamide / 36 h / -78 °C

2: 60 percent / 30 °C

3: 95 percent / 10-camphorsulfonic acid

4: 90 percent / LiAlH₄ / 0 - 20 °C

5: 94 percent / triethylamine

6: 88 percent / LiAlH₄

7: 93 percent / diisobutylaluminium hydride / toluene

8: 70 percent / NaH; n-BuLi / 0 °C

With lithium aluminium tetrahydride; n-butyllithium; (1S)-10-camphorsulfonic acid; sodium hydride; diisobutylaluminium hydride; triethylamine; lithium diisopropyl amide; In N,N,N,N,N,N-hexamethylphosphoric triamide; toluene; 8: Dess-Martin oxidation;
DOI:10.1002/1521-3773(20020415)41:8<1404::AID-ANIE1404>3.0.CO;2-G