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

Base Information

Chemical Name:(3S,5S,6S,7S,8S)-3,5-Dihydroxy-7-(4-methoxy-benzyloxy)-4,4,6,8-tetramethyl-undec-10-enoic acid tert-butyl ester
CAS No.:461044-33-7
Molecular Formula:C₂₇H₄₄O₆
Molecular Weight:464.643
Hs Code.:

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

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

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

There total 11 articles about (3S,5S,6S,7S,8S)-3,5-Dihydroxy-7-(4-methoxy-benzyloxy)-4,4,6,8-tetramethyl-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: 83.0%

: 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

: 461044-33-7
(3S,5S,6S,7S,8S)-3,5-Dihydroxy-7-(4-methoxy-benzyloxy)-4,4,6,8-tetramethyl-undec-10-enoic acid tert-butyl ester

Guidance literature:: With tetramethylammonium triacetoxyborohydride; at -30 ℃;
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

: 461044-33-7
(3S,5S,6S,7S,8S)-3,5-Dihydroxy-7-(4-methoxy-benzyloxy)-4,4,6,8-tetramethyl-undec-10-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 8 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

7: 83 percent / Me₄NBH(OAc)3 / -30 °C

With lithium aluminium tetrahydride; n-butyllithium; (1S)-10-camphorsulfonic acid; sodium hydride; diisobutylaluminium hydride; triethylamine; tetramethylammonium triacetoxyborohydride; 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

: 461044-33-7
(3S,5S,6S,7S,8S)-3,5-Dihydroxy-7-(4-methoxy-benzyloxy)-4,4,6,8-tetramethyl-undec-10-enoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 10 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

9: 83 percent / Me₄NBH(OAc)3 / -30 °C

With lithium aluminium tetrahydride; n-butyllithium; (1S)-10-camphorsulfonic acid; sodium hydride; diisobutylaluminium hydride; triethylamine; tetramethylammonium triacetoxyborohydride; 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