(E)-(2R,3S,6R,9S,12R,14S)-9-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,6,8,12,14-pentamethyl-hexadec-7-en-15-yne-5,11-dione

Base Information

Chemical Name:(E)-(2R,3S,6R,9S,12R,14S)-9-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,6,8,12,14-pentamethyl-hexadec-7-en-15-yne-5,11-dione
CAS No.:164592-86-3
Molecular Formula:C₄₃H₈₀O₆Si₂
Molecular Weight:749.276
Hs Code.:

(E)-(2R,3S,6R,9S,12R,14S)-9-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,6,8,12,14-pentamethyl-hexadec-7-en-15-yne-5,11-dione

Synonyms:(E)-(2R,3S,6R,9S,12R,14S)-9-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,6,8,12,14-pentamethyl-hexadec-7-en-15-yne-5,11-dione

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Chemical Property of (E)-(2R,3S,6R,9S,12R,14S)-9-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,6,8,12,14-pentamethyl-hexadec-7-en-15-yne-5,11-dione

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Technology Process of (E)-(2R,3S,6R,9S,12R,14S)-9-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,6,8,12,14-pentamethyl-hexadec-7-en-15-yne-5,11-dione

There total 32 articles about (E)-(2R,3S,6R,9S,12R,14S)-9-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,6,8,12,14-pentamethyl-hexadec-7-en-15-yne-5,11-dione 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: 90.0%

: 164592-84-1
(2S,3R)-1-(2-{(E)-(1R,4S)-4-(tert-Butyl-dimethyl-silanyloxy)-5-[2-((1R,3S)-1,3-dimethyl-pent-4-ynyl)-[1,3]dithian-2-yl]-1,3-dimethyl-pent-2-enyl}-[1,3]dithian-2-yl)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butan-2-ol

: 164592-86-3
(E)-(2R,3S,6R,9S,12R,14S)-9-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,6,8,12,14-pentamethyl-hexadec-7-en-15-yne-5,11-dione

Guidance literature:: With bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; methanol; water;
DOI:10.1021/ja00124a043

Reference yield:

: 186448-80-6
(E)-(2R,5R)-5-{2-[(2S,3R)-2-(4-Methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-ene-1,2-diol

: 164592-86-3
(E)-(2R,3S,6R,9S,12R,14S)-9-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,6,8,12,14-pentamethyl-hexadec-7-en-15-yne-5,11-dione

Guidance literature:: Multi-step reaction with 9 steps

1: 85 percent / Et₃N, DMAP / CH₂Cl₂ / 16 h / Ambient temperature

2: K₂CO₃ / methanol / 1 h / Ambient temperature

3: t-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; pentane / -78 - -55 °C

4: 84 percent / 2,6-lutidine / -78 °C

5: 78 percent / TsOH / acetone

6: 94 percent / HMPT / tetrahydrofuran

7: 89 percent / n-BuLi / tetrahydrofuran

8: 92 percent / DDQ / CH₂Cl₂; H₂O

9: 90 percent / PhI(O₂CCF₃)2 / tetrahydrofuran; methanol; H₂O

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; tert.-butyl lithium; potassium carbonate; toluene-4-sulfonic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; acetone; pentane;
DOI:10.1021/ja963066w

Reference yield:

: 164714-14-1
{(1R,2R,4S)-4-[(2R,3S)-4-{2-[(E)-(R)-3-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-1-methyl-but-2-enyl]-[1,3]dithian-2-yl}-3-(4-methoxy-benzyloxy)-2-methyl-butyl]-2-methoxy-cyclohexyloxy}-triisopropyl-silane

: 164592-86-3
(E)-(2R,3S,6R,9S,12R,14S)-9-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-1-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-2,6,8,12,14-pentamethyl-hexadec-7-en-15-yne-5,11-dione

Guidance literature:: Multi-step reaction with 10 steps

1: 73 percent / camphorsulfonic acid / methanol / 2 h / Ambient temperature

2: 85 percent / Et₃N, DMAP / CH₂Cl₂ / 16 h / Ambient temperature

3: K₂CO₃ / methanol / 1 h / Ambient temperature

4: t-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran; pentane / -78 - -55 °C

5: 84 percent / 2,6-lutidine / -78 °C

6: 78 percent / TsOH / acetone

7: 94 percent / HMPT / tetrahydrofuran

8: 89 percent / n-BuLi / tetrahydrofuran

9: 92 percent / DDQ / CH₂Cl₂; H₂O

10: 90 percent / PhI(O₂CCF₃)2 / tetrahydrofuran; methanol; H₂O

With 2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; n-butyllithium; camphor-10-sulfonic acid; tert.-butyl lithium; potassium carbonate; toluene-4-sulfonic acid; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; bis-[(trifluoroacetoxy)iodo]benzene; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; acetone; pentane;
DOI:10.1021/ja963066w