(2S,4S,5S)-4-((2R,3R,6S,8S,9R,10S,11Z,13S,15S,16R,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,3R,6S,8S,9R,10S,11Z,13S,15S,16R,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.:792921-87-0
Molecular Formula:C₇₈H₁₂₈O₈Si₄
Molecular Weight:1306.21
Hs Code.:

(2S,4S,5S)-4-((2R,3R,6S,8S,9R,10S,11Z,13S,15S,16R,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

Synonyms:(2S,4S,5S)-4-((2R,3R,6S,8S,9R,10S,11Z,13S,15S,16R,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

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Chemical Property of (2S,4S,5S)-4-((2R,3R,6S,8S,9R,10S,11Z,13S,15S,16R,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

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Technology Process of (2S,4S,5S)-4-((2R,3R,6S,8S,9R,10S,11Z,13S,15S,16R,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 48 articles about (2S,4S,5S)-4-((2R,3R,6S,8S,9R,10S,11Z,13S,15S,16R,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: 99.0%

: 792921-72-3
(2S,3R,6S,8S,9R,10S,11Z,13S,15S,16R,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

: 69739-34-0
t-butyldimethylsiyl triflate

: 792921-87-0
(2S,4S,5S)-4-((2R,3R,6S,8S,9R,10S,11Z,13S,15S,16R,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

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane;
DOI:10.1002/anie.200460593

Reference yield:

: 792921-69-8
(3S,4R,5E)-3-(tert-butyldimethylsilyloxy)-N-methoxy-N,4-dimethyl-7-(trityloxy)hept-5-enamide

: 792921-87-0
(2S,4S,5S)-4-((2R,3R,6S,8S,9R,10S,11Z,13S,15S,16R,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

Guidance literature:: Multi-step reaction with 10 steps

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

1.2: 93 percent / tetrahydrofuran; hexane / -78 - 0 °C

2.1: 79 percent / i-PrOH / (S,S)-Noyori catalyst

3.1: 91 percent / hydrogen / Lindlar catalyst / toluene / 1 h

4.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

5.1: 67 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 21 h / 0 °C

6.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

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

7.2: 2.60 g / tetrahydrofuran; H₂O / 12 h

8.1: 76 percent / NiCl₂*6H₂O; NaBH₄ / methanol; tetrahydrofuran / 0 °C

9.1: 70 percent / NaBH₄ / methanol / 2 h / 0 °C

10.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

With pyridine; 2,6-dimethylpyridine; barium dihydroxide; sodium tetrahydroborate; n-butyllithium; hydrogen; Dess-Martin periodane; pyridine hydrogenfluoride; isopropyl alcohol; nickel dichloride; Lindlar's catalyst; (S,S)-Noyori catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; toluene; 6.1: Dess-Martin oxidation / 7.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2007.05.033

Reference yield:

: 792921-79-0
(4R,5S,2E)-5,7-bis(tert-butyldimethylsilyloxy)-4-methylhept-2-en-1-ol

: 792921-87-0
(2S,4S,5S)-4-((2R,3R,6S,8S,9R,10S,11Z,13S,15S,16R,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

Guidance literature:: Multi-step reaction with 15 steps

1.1: 100 percent / 4-(dimethylamino)pyridine; pyridine / 18 h / Heating

2.1: 89 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 20 °C

3.1: sulfur trioxide*pyridine complex; Et₃N; DMSO / CH₂Cl₂ / 0 - 20 °C

4.1: 2-methyl-2-butene; NaH₂PO₄*H₂O; NaClO₂ / H₂O; tetrahydrofuran / 2 h

5.1: 2.65 g / 4-(dimethylamino)pyridine; Et₃N; DCC / CH₂Cl₂ / 0 - 20 °C

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

6.2: 93 percent / tetrahydrofuran; hexane / -78 - 0 °C

7.1: 79 percent / i-PrOH / (S,S)-Noyori catalyst

8.1: 91 percent / hydrogen / Lindlar catalyst / toluene / 1 h

9.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

10.1: 67 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 21 h / 0 °C

11.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

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

12.2: 2.60 g / tetrahydrofuran; H₂O / 12 h

13.1: 76 percent / NiCl₂*6H₂O; NaBH₄ / methanol; tetrahydrofuran / 0 °C

14.1: 70 percent / NaBH₄ / methanol / 2 h / 0 °C

15.1: 99 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; hydrogen; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; isopropyl alcohol; nickel dichloride; Lindlar's catalyst; (S,S)-Noyori catalyst; In tetrahydrofuran; methanol; hexane; dichloromethane; water; toluene; 11.1: Dess-Martin oxidation / 12.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2007.05.033