(2S,4S,5S)-4-[(2R,3S,6S,8R,9R,10S,11Z,13S,15S,16S,17E)-3,9,13,15-tetrakis(tert-butyldimethylsilyloxy)-6,8,10,16-tetramethyl-19-(trityloxy)nonadeca-11,17-dien-2-yl]-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane

Base Information

• Chemical Name: (2S,4S,5S)-4-[(2R,3S,6S,8R,9R,10S,11Z,13S,15S,16S,17E)-3,9,13,15-tetrakis(tert-butyldimethylsilyloxy)-6,8,10,16-tetramethyl-19-(trityloxy)nonadeca-11,17-dien-2-yl]-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane
• CAS No.: 871236-89-4
• Molecular Formula: C₇₈H₁₂₈O₈Si₄
• Molecular Weight: 1306.21

Synonyms:(2S,4S,5S)-4-[(2R,3S,6S,8R,9R,10S,11Z,13S,15S,16S,17E)-3,9,13,15-tetrakis(tert-butyldimethylsilyloxy)-6,8,10,16-tetramethyl-19-(trityloxy)nonadeca-11,17-dien-2-yl]-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane

Chemical Property of (2S,4S,5S)-4-[(2R,3S,6S,8R,9R,10S,11Z,13S,15S,16S,17E)-3,9,13,15-tetrakis(tert-butyldimethylsilyloxy)-6,8,10,16-tetramethyl-19-(trityloxy)nonadeca-11,17-dien-2-yl]-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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Useful:

Technology Process of (2S,4S,5S)-4-[(2R,3S,6S,8R,9R,10S,11Z,13S,15S,16S,17E)-3,9,13,15-tetrakis(tert-butyldimethylsilyloxy)-6,8,10,16-tetramethyl-19-(trityloxy)nonadeca-11,17-dien-2-yl]-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane

There total 40 articles about (2S,4S,5S)-4-[(2R,3S,6S,8R,9R,10S,11Z,13S,15S,16S,17E)-3,9,13,15-tetrakis(tert-butyldimethylsilyloxy)-6,8,10,16-tetramethyl-19-(trityloxy)nonadeca-11,17-dien-2-yl]-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane 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: 93.0%

(2S,3S,6S,8R,9R,10S,11Z,13S,15S,16S,17E)-9,13,15-tris(tert-butyldimethylsilyloxy)-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8,10,16-tetramethyl-19-(trityloxy)nonadeca-11,17-dien-3-ol (871236-79-2) + t-butyldimethylsiyl triflate (69739-34-0) → (2S,4S,5S)-4-[(2R,3S,6S,8R,9R,10S,11Z,13S,15S,16S,17E)-3,9,13,15-tetrakis(tert-butyldimethylsilyloxy)-6,8,10,16-tetramethyl-19-(trityloxy)nonadeca-11,17-dien-2-yl]-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane (871236-89-4)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1016/j.tet.2007.05.033

Reference yield:

(2R,3S)-3,5-bis(tert-butyldimethylsilyloxy)-2-methylpentanal (911837-33-7) → (2S,4S,5S)-4-[(2R,3S,6S,8R,9R,10S,11Z,13S,15S,16S,17E)-3,9,13,15-tetrakis(tert-butyldimethylsilyloxy)-6,8,10,16-tetramethyl-19-(trityloxy)nonadeca-11,17-dien-2-yl]-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane (871236-89-4)

Guidance literature:

Multi-step reaction with 19 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

15.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

16.1: activated Ba(OH)2 / tetrahydrofuran / 0.5 h / 20 °C

16.2: 2.04 g / tetrahydrofuran; H₂O / 12 h

17.1: 76 percent / NiCl₂*6H₂O; NaBH₄ / methanol; tetrahydrofuran / 0 °C

18.1: 36 percent / NaBH₄ / methanol / 2 h / 0 °C

19.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; barium dihydroxide; sodium chlorite; sodium tetrahydroborate; 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; nickel dichloride; Lindlar's catalyst; (S,S)-Noyori catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene; 1.2: Wadsworth-Horner-Emmons reaction / 5.1: Dess-Martin oxidation / 15.1: Dess-Martin oxidation / 16.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.tet.2007.05.033

Reference yield:

(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-4-(prop-1-en-2-yl)-1,3-dioxane (951154-92-0) → (2S,4S,5S)-4-[(2R,3S,6S,8R,9R,10S,11Z,13S,15S,16S,17E)-3,9,13,15-tetrakis(tert-butyldimethylsilyloxy)-6,8,10,16-tetramethyl-19-(trityloxy)nonadeca-11,17-dien-2-yl]-2-(4-methoxyphenyl)-5-methyl-1,3-dioxane (871236-89-4)

Guidance literature:

Multi-step reaction with 21 steps

1.1: BH₃*SMe₂; cyclohexene / tetrahydrofuran / 0 - 20 °C

1.2: 5.61 g / NaOH; aq. H₂O₂ / tetrahydrofuran / 1 h / 0 - 50 °C

2.1: 98 percent / PPh₃; imidazole; iodine / CH₂Cl₂ / 20 h / 20 °C

3.1: LDA; LiCl / tetrahydrofuran; hexane / -78 - 20 °C

3.2: 88 percent / tetrahydrofuran; hexane / 0 - 20 °C

4.1: 79 percent / LDA; BH₃*NH₃ / tetrahydrofuran; hexane / -78 - 20 °C

5.1: imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

6.1: 1.23 g / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.58 h / -78 - 0 °C

7.1: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

8.1: PPh₃ / CH₂Cl₂ / 0 °C

8.2: 0.58 g / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

9.1: BuLi / tetrahydrofuran; hexane / 0.67 h / -78 °C

9.2: 96 percent / aq. NH₄Cl / tetrahydrofuran; hexane

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

17.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

18.1: activated Ba(OH)2 / tetrahydrofuran / 0.5 h / 20 °C

18.2: 2.04 g / tetrahydrofuran; H₂O / 12 h

19.1: 76 percent / NiCl₂*6H₂O; NaBH₄ / methanol; tetrahydrofuran / 0 °C

20.1: 36 percent / NaBH₄ / methanol / 2 h / 0 °C

21.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; barium dihydroxide; sodium tetrahydroborate; n-butyllithium; borane-ammonia complex; dimethylsulfide borane complex; water; hydrogen; iodine; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triphenylphosphine; isopropyl alcohol; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; nickel dichloride; lithium diisopropyl amide; cyclohexene; Lindlar's catalyst; (S,S)-Noyori catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 3.2: Meyers asymmetric alkylation / 7.1: Dess-Martin oxidation / 9.1: Corey-Fuchs reaction / 17.1: Dess-Martin oxidation / 18.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.tet.2007.05.033

upstream raw materials:

(2S,3S,6S,8R,9R,10S,11Z,13S,15S,16S,17E)-9,13,15-tris(tert-butyldimethylsilyloxy)-2-[(2S,4S,5S)-2-(4-methoxyphenyl)-5-methyl-1,3-dioxan-4-yl]-6,8,10,16-tetramethyl-19-(trityloxy)nonadeca-11,17-dien-3-ol

t-butyldimethylsiyl triflate

{3(R)-[2(S)-(4-methoxyphenyl)-5(S)-methyl[1,3]dioxan-4(S)-yl]-2-oxobutyl}phosphonic acid dimethyl ester

(2R,3S)-3,5-bis(tert-butyldimethylsilyloxy)-2-methylpentanal

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