(2R,4R,5R,6S,7Z,9S,11S,12S,13E)-5,9,11-tris(tert-butyldimethylsilyloxy)-2,4,6,12-tetramethyl-15-(trityloxy)pentadeca-7,13-dien-1-ol

Base Information

Chemical Name:(2R,4R,5R,6S,7Z,9S,11S,12S,13E)-5,9,11-tris(tert-butyldimethylsilyloxy)-2,4,6,12-tetramethyl-15-(trityloxy)pentadeca-7,13-dien-1-ol
CAS No.:871236-76-9
Molecular Formula:C₅₆H₉₂O₅Si₃
Molecular Weight:929.6
Hs Code.:

Synonyms:(2R,4R,5R,6S,7Z,9S,11S,12S,13E)-5,9,11-tris(tert-butyldimethylsilyloxy)-2,4,6,12-tetramethyl-15-(trityloxy)pentadeca-7,13-dien-1-ol

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Chemical Property of (2R,4R,5R,6S,7Z,9S,11S,12S,13E)-5,9,11-tris(tert-butyldimethylsilyloxy)-2,4,6,12-tetramethyl-15-(trityloxy)pentadeca-7,13-dien-1-ol

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Technology Process of (2R,4R,5R,6S,7Z,9S,11S,12S,13E)-5,9,11-tris(tert-butyldimethylsilyloxy)-2,4,6,12-tetramethyl-15-(trityloxy)pentadeca-7,13-dien-1-ol

There total 32 articles about (2R,4R,5R,6S,7Z,9S,11S,12S,13E)-5,9,11-tris(tert-butyldimethylsilyloxy)-2,4,6,12-tetramethyl-15-(trityloxy)pentadeca-7,13-dien-1-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: 66.0%

: 871236-75-8
[(2E,4S,5S,7S,8Z,10S,11R,12R,14R)-5,7,11,15-tetrakis(tert-butyldimethylsilyloxy)-4,10,12,14-tetramethylpentadeca-2,8-dienyloxy]triphenylmethane

: 871236-76-9
(2R,4R,5R,6S,7Z,9S,11S,12S,13E)-5,9,11-tris(tert-butyldimethylsilyloxy)-2,4,6,12-tetramethyl-15-(trityloxy)pentadeca-7,13-dien-1-ol

Guidance literature:: With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 0 ℃; for 48h;
DOI:10.1016/j.tet.2007.05.033

Reference yield:

: 911837-33-7
(2R,3S)-3,5-bis(tert-butyldimethylsilyloxy)-2-methylpentanal

: 871236-76-9
(2R,4R,5R,6S,7Z,9S,11S,12S,13E)-5,9,11-tris(tert-butyldimethylsilyloxy)-2,4,6,12-tetramethyl-15-(trityloxy)pentadeca-7,13-dien-1-ol

Guidance literature:: Multi-step reaction with 14 steps

1.1: NaH / tetrahydrofuran; various solvent(s) / -78 - 20 °C

1.2: tetrahydrofuran; various solvent(s) / 1 h / 0 °C

1.3: 1.68 g / various solvents / -78 - 20 °C

2.1: 97 percent / diisobutylaluminum hydride / hexane; CH₂Cl₂ / 1 h / -78 °C

3.1: 94 percent / 4-(dimethylamino)pyridine; pyridine / 18 h / Heating

4.1: 82 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 20 °C

5.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

6.1: NaH₂PO₄*H₂O; NaClO₂; 2-methyl-2-butene / tetrahydrofuran; H₂O / 2 h

7.1: 0.37 g / Et₃N; 4-(dimethylamino)pyridine; DCC / CH₂Cl₂ / 0 - 20 °C

8.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

8.2: 98 percent / tetrahydrofuran; hexane / -78 - 0 °C

9.1: 87 percent / i-PrOH / (S,S)-Noyori catalyst / 12 h

10.1: 90 percent / hydrogen / Lindlar catalyst / toluene / 1 h

11.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

12.1: 84 percent / DDQ; H₂O / CH₂Cl₂ / 1 h

13.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

14.1: 66 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 48 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; 2-methyl-but-2-ene; water; hydrogen; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; dicyclohexyl-carbodiimide; isopropyl alcohol; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; (S,S)-Noyori catalyst; In tetrahydrofuran; hexane; dichloromethane; water; toluene; 1.2: Wadsworth-Horner-Emmons reaction / 5.1: Dess-Martin oxidation;
DOI:10.1016/j.tet.2007.05.033

Reference yield:

: C₂₉H₅₁NO₄Si₂

: 871236-76-9
(2R,4R,5R,6S,7Z,9S,11S,12S,13E)-5,9,11-tris(tert-butyldimethylsilyloxy)-2,4,6,12-tetramethyl-15-(trityloxy)pentadeca-7,13-dien-1-ol

Guidance literature:: Multi-step reaction with 16 steps

1.1: 87 percent / LiBH₄ / methanol; tetrahydrofuran

2.1: Dess-Martin periodinane

3.1: NaH / tetrahydrofuran; various solvent(s) / -78 - 20 °C

3.2: tetrahydrofuran; various solvent(s) / 1 h / 0 °C

3.3: 1.68 g / various solvents / -78 - 20 °C

4.1: 97 percent / diisobutylaluminum hydride / hexane; CH₂Cl₂ / 1 h / -78 °C

5.1: 94 percent / 4-(dimethylamino)pyridine; pyridine / 18 h / Heating

6.1: 82 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 20 °C

7.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

8.1: NaH₂PO₄*H₂O; NaClO₂; 2-methyl-2-butene / tetrahydrofuran; H₂O / 2 h

9.1: 0.37 g / Et₃N; 4-(dimethylamino)pyridine; DCC / CH₂Cl₂ / 0 - 20 °C

10.1: n-BuLi / tetrahydrofuran; hexane / -78 - 0 °C

10.2: 98 percent / tetrahydrofuran; hexane / -78 - 0 °C

11.1: 87 percent / i-PrOH / (S,S)-Noyori catalyst / 12 h

12.1: 90 percent / hydrogen / Lindlar catalyst / toluene / 1 h

13.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

14.1: 84 percent / DDQ; H₂O / CH₂Cl₂ / 1 h

15.1: 94 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

16.1: 66 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 48 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; sodium chlorite; sodium dihydrogenphosphate; lithium borohydride; n-butyllithium; 2-methyl-but-2-ene; water; hydrogen; sodium hydride; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; dicyclohexyl-carbodiimide; isopropyl alcohol; 2,3-dicyano-5,6-dichloro-p-benzoquinone; Lindlar's catalyst; (S,S)-Noyori catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene; 2.1: Dess-Martin oxidation / 3.2: Wadsworth-Horner-Emmons reaction / 7.1: Dess-Martin oxidation;
DOI:10.1016/j.tet.2007.05.033