(3R,4R,13S)-1-Benzyloxy-3,13-bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4-methyl-pentadec-9-yn-6-one

Base Information

Chemical Name:(3R,4R,13S)-1-Benzyloxy-3,13-bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4-methyl-pentadec-9-yn-6-one
CAS No.:794520-81-3
Molecular Formula:C₄₃H₇₀O₆Si₂
Molecular Weight:739.196
Hs Code.:

Synonyms:(3R,4R,13S)-1-Benzyloxy-3,13-bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4-methyl-pentadec-9-yn-6-one

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Chemical Property of (3R,4R,13S)-1-Benzyloxy-3,13-bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4-methyl-pentadec-9-yn-6-one

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Technology Process of (3R,4R,13S)-1-Benzyloxy-3,13-bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4-methyl-pentadec-9-yn-6-one

There total 12 articles about (3R,4R,13S)-1-Benzyloxy-3,13-bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4-methyl-pentadec-9-yn-6-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%

: 8-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-dec-4-ynal

: 794520-80-2
[(1R,2S)-3-Benzenesulfonyl-1-(2-benzyloxy-ethyl)-2-methyl-propoxy]-tert-butyl-dimethyl-silane

: 794520-81-3
(3R,4R,13S)-1-Benzyloxy-3,13-bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4-methyl-pentadec-9-yn-6-one

Guidance literature:: 8-(tert-butyl-dimethyl-silanyloxy)-10-(4-methoxy-benzyloxy)-dec-4-ynal; [(1R,2S)-3-Benzenesulfonyl-1-(2-benzyloxy-ethyl)-2-methyl-propoxy]-tert-butyl-dimethyl-silane; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

With dimethyl pimelimidate dihydrochloride; sodium hydrogencarbonate; In dichloromethane; at 23 ℃; for 0.666667h;

With samarium diiodide; In tetrahydrofuran; methanol; at 0 ℃; for 0.666667h; Further stages.;
DOI:10.1016/j.tetlet.2004.08.156

Reference yield:

: 22273-77-4
((but-3-yn-1-yloxy)methyl)benzene

: 794520-81-3
(3R,4R,13S)-1-Benzyloxy-3,13-bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4-methyl-pentadec-9-yn-6-one

Guidance literature:: Multi-step reaction with 11 steps

1.1: BuLi / tetrahydrofuran / 0.5 h / -78 °C

1.2: 87 percent / tetrahydrofuran / 6 h / -78 - 0 °C

2.1: 98 percent / LiAlH₄ / tetrahydrofuran / 3 h / 23 °C

3.1: 95 percent / L-(+)-DET; Ti(OiPr)4; TBHP / CH₂Cl₂ / 12 h / -20 °C

4.1: tetrahydrofuran; diethyl ether / 19 h / -20 °C

4.2: 68 percent / NaIO₄ / methanol; H₂O / 0.5 h / 23 °C / pH 5.5

5.1: 77 percent / I₂; PPh₃; imidazole / tetrahydrofuran / 1.5 h / 0 °C

6.1: 85 percent / dimethylformamide / 10 h / 23 °C

7.1: Et₃N; DMAP / CH₂Cl₂ / 2.5 h / 23 °C

8.1: toluene / 18 h / Heating

9.1: K₂CO₃ / methanol / 10 h / 23 °C

10.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

11.1: BuLi / tetrahydrofuran / 0.5 h / -78 °C

11.2: DMPI; NaHCO₃ / CH₂Cl₂ / 0.67 h / 23 °C

11.3: 86 percent / SmI₂ / methanol; tetrahydrofuran / 0.67 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; n-butyllithium; diethyl (2R,3R)-tartrate; iodine; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tetlet.2004.08.156

Reference yield:

: 22273-79-6
5-benzyloxy-2-pentyn-1-ol

: 794520-81-3
(3R,4R,13S)-1-Benzyloxy-3,13-bis-(tert-butyl-dimethyl-silanyloxy)-15-(4-methoxy-benzyloxy)-4-methyl-pentadec-9-yn-6-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: 98 percent / LiAlH₄ / tetrahydrofuran / 3 h / 23 °C

2.1: 95 percent / L-(+)-DET; Ti(OiPr)4; TBHP / CH₂Cl₂ / 12 h / -20 °C

3.1: tetrahydrofuran; diethyl ether / 19 h / -20 °C

3.2: 68 percent / NaIO₄ / methanol; H₂O / 0.5 h / 23 °C / pH 5.5

4.1: 77 percent / I₂; PPh₃; imidazole / tetrahydrofuran / 1.5 h / 0 °C

5.1: 85 percent / dimethylformamide / 10 h / 23 °C

6.1: Et₃N; DMAP / CH₂Cl₂ / 2.5 h / 23 °C

7.1: toluene / 18 h / Heating

8.1: K₂CO₃ / methanol / 10 h / 23 °C

9.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / 0 °C

10.1: BuLi / tetrahydrofuran / 0.5 h / -78 °C

10.2: DMPI; NaHCO₃ / CH₂Cl₂ / 0.67 h / 23 °C

10.3: 86 percent / SmI₂ / methanol; tetrahydrofuran / 0.67 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; lithium aluminium tetrahydride; n-butyllithium; diethyl (2R,3R)-tartrate; iodine; potassium carbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.tetlet.2004.08.156