(2E,9E,11E)-(4R,5S,6S,8S,13R,14R)-15-((1S,3R,4S)-3,4-Bis-triethylsilanyloxy-cyclopentyl)-4-methoxy-1-(4-methoxy-benzyloxy)-3,5,9,13-tetramethyl-14-triethylsilanyloxy-8-triisopropylsilanyloxy-pentadeca-2,9,11-trien-6-ol

Base Information

Chemical Name:(2E,9E,11E)-(4R,5S,6S,8S,13R,14R)-15-((1S,3R,4S)-3,4-Bis-triethylsilanyloxy-cyclopentyl)-4-methoxy-1-(4-methoxy-benzyloxy)-3,5,9,13-tetramethyl-14-triethylsilanyloxy-8-triisopropylsilanyloxy-pentadeca-2,9,11-trien-6-ol
CAS No.:691869-51-9
Molecular Formula:C₆₀H₁₁₄O₈Si₄
Molecular Weight:1075.9
Hs Code.:

(2E,9E,11E)-(4R,5S,6S,8S,13R,14R)-15-((1S,3R,4S)-3,4-Bis-triethylsilanyloxy-cyclopentyl)-4-methoxy-1-(4-methoxy-benzyloxy)-3,5,9,13-tetramethyl-14-triethylsilanyloxy-8-triisopropylsilanyloxy-pentadeca-2,9,11-trien-6-ol

Synonyms:(2E,9E,11E)-(4R,5S,6S,8S,13R,14R)-15-((1S,3R,4S)-3,4-Bis-triethylsilanyloxy-cyclopentyl)-4-methoxy-1-(4-methoxy-benzyloxy)-3,5,9,13-tetramethyl-14-triethylsilanyloxy-8-triisopropylsilanyloxy-pentadeca-2,9,11-trien-6-ol

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Chemical Property of (2E,9E,11E)-(4R,5S,6S,8S,13R,14R)-15-((1S,3R,4S)-3,4-Bis-triethylsilanyloxy-cyclopentyl)-4-methoxy-1-(4-methoxy-benzyloxy)-3,5,9,13-tetramethyl-14-triethylsilanyloxy-8-triisopropylsilanyloxy-pentadeca-2,9,11-trien-6-ol

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Technology Process of (2E,9E,11E)-(4R,5S,6S,8S,13R,14R)-15-((1S,3R,4S)-3,4-Bis-triethylsilanyloxy-cyclopentyl)-4-methoxy-1-(4-methoxy-benzyloxy)-3,5,9,13-tetramethyl-14-triethylsilanyloxy-8-triisopropylsilanyloxy-pentadeca-2,9,11-trien-6-ol

There total 22 articles about (2E,9E,11E)-(4R,5S,6S,8S,13R,14R)-15-((1S,3R,4S)-3,4-Bis-triethylsilanyloxy-cyclopentyl)-4-methoxy-1-(4-methoxy-benzyloxy)-3,5,9,13-tetramethyl-14-triethylsilanyloxy-8-triisopropylsilanyloxy-pentadeca-2,9,11-trien-6-ol 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: 99.0%

: 4-nitro-benzoic acid 10-(3,4-bis-triethylsilanyloxy-cyclopentyl)-1-[2-methoxy-5-(4-methoxy-benzyloxy)-1,3-dimethyl-pent-3-enyl]-4,8-dimethyl-9-triethylsilanyloxy-3-triisopropylsilanyloxy-deca-4,6-dienyl ester

: 691869-51-9
(2E,9E,11E)-(4R,5S,6S,8S,13R,14R)-15-((1S,3R,4S)-3,4-Bis-triethylsilanyloxy-cyclopentyl)-4-methoxy-1-(4-methoxy-benzyloxy)-3,5,9,13-tetramethyl-14-triethylsilanyloxy-8-triisopropylsilanyloxy-pentadeca-2,9,11-trien-6-ol

Guidance literature:: With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 1.5h;
DOI:10.1021/ol049701h

Reference yield:

: 58794-19-7
3-allyl-hex-5-enal

: 691869-51-9
(2E,9E,11E)-(4R,5S,6S,8S,13R,14R)-15-((1S,3R,4S)-3,4-Bis-triethylsilanyloxy-cyclopentyl)-4-methoxy-1-(4-methoxy-benzyloxy)-3,5,9,13-tetramethyl-14-triethylsilanyloxy-8-triisopropylsilanyloxy-pentadeca-2,9,11-trien-6-ol

Guidance literature:: Multi-step reaction with 10 steps

1.1: dibutylboron triflate; Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

1.2: 88 percent / Et₃N / CH₂Cl₂ / -78 - 0 °C

2.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 - 0 °C

3.1: 91 percent / Grubb's catalyst / 1,2-dichloro-ethane / 0.33 h / 20 °C

4.1: 87 percent / 4-methylmorpholine N-oxide; OsO₄ / acetone; H₂O / 18 h / 20 °C

5.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 - 0 °C

6.1: 58 percent / LiBH₄ / tetrahydrofuran; methanol / 24 h / 20 °C

7.1: 98 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 24 h / 20 °C

8.1: 97 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 16 h / 20 °C

9.1: LiHMDS / tetrahydrofuran / 0.67 h / -78 °C

9.2: 80 percent / tetrahydrofuran / -78 - 20 °C

10.1: 99 percent / DIBAl-H / CH₂Cl₂; hexane / 1.5 h / -78 °C

With 2,6-dimethylpyridine; osmium(VIII) oxide; lithium borohydride; di-n-butylboryl trifluoromethanesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; acetone; 1.1: Evans aldol reaction / 1.2: Evans aldol reaction / 3.1: ring-closing metathesis / 7.1: Mitsunobu reaction;
DOI:10.1021/ol049701h

Reference yield:

: 691869-47-3
(S)-3-((2S,3R)-5-Allyl-3-hydroxy-2-methyl-oct-7-enoyl)-4-isopropyl-oxazolidin-2-one

: 691869-51-9
(2E,9E,11E)-(4R,5S,6S,8S,13R,14R)-15-((1S,3R,4S)-3,4-Bis-triethylsilanyloxy-cyclopentyl)-4-methoxy-1-(4-methoxy-benzyloxy)-3,5,9,13-tetramethyl-14-triethylsilanyloxy-8-triisopropylsilanyloxy-pentadeca-2,9,11-trien-6-ol

Guidance literature:: Multi-step reaction with 9 steps

1.1: 85 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -78 - 0 °C

2.1: 91 percent / Grubb's catalyst / 1,2-dichloro-ethane / 0.33 h / 20 °C

3.1: 87 percent / 4-methylmorpholine N-oxide; OsO₄ / acetone; H₂O / 18 h / 20 °C

4.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.75 h / -78 - 0 °C

5.1: 58 percent / LiBH₄ / tetrahydrofuran; methanol / 24 h / 20 °C

6.1: 98 percent / PPh₃; diethyl azodicarboxylate / tetrahydrofuran / 24 h / 20 °C

7.1: 97 percent / m-CPBA; NaHCO₃ / CH₂Cl₂ / 16 h / 20 °C

8.1: LiHMDS / tetrahydrofuran / 0.67 h / -78 °C

8.2: 80 percent / tetrahydrofuran / -78 - 20 °C

9.1: 99 percent / DIBAl-H / CH₂Cl₂; hexane / 1.5 h / -78 °C

With 2,6-dimethylpyridine; osmium(VIII) oxide; lithium borohydride; diisobutylaluminium hydride; sodium hydrogencarbonate; 4-methylmorpholine N-oxide; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; acetone; 2.1: ring-closing metathesis / 6.1: Mitsunobu reaction;
DOI:10.1021/ol049701h