13(S),15(S)-bis(tert-butyldimethylsilanyloxy)-2(S)-[2(S)-(4-methoxyphenyl)-5(S)-methyl[1,3]dioxan-4(S)-yl]-9(R)-(4-methoxybenzyloxy)-6(R),8(S),10(S),16(S)-tetramethyl-19-trityloxynonadeca-11,17-dien-3(R)-ol

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Chemical Name:13(S),15(S)-bis(tert-butyldimethylsilanyloxy)-2(S)-[2(S)-(4-methoxyphenyl)-5(S)-methyl[1,3]dioxan-4(S)-yl]-9(R)-(4-methoxybenzyloxy)-6(R),8(S),10(S),16(S)-tetramethyl-19-trityloxynonadeca-11,17-dien-3(R)-ol
CAS No.:951154-83-9
Molecular Formula:C₇₄H₁₀₈O₉Si₂
Molecular Weight:1197.84
Hs Code.:

13(S),15(S)-bis(tert-butyldimethylsilanyloxy)-2(S)-[2(S)-(4-methoxyphenyl)-5(S)-methyl[1,3]dioxan-4(S)-yl]-9(R)-(4-methoxybenzyloxy)-6(R),8(S),10(S),16(S)-tetramethyl-19-trityloxynonadeca-11,17-dien-3(R)-ol

Synonyms:13(S),15(S)-bis(tert-butyldimethylsilanyloxy)-2(S)-[2(S)-(4-methoxyphenyl)-5(S)-methyl[1,3]dioxan-4(S)-yl]-9(R)-(4-methoxybenzyloxy)-6(R),8(S),10(S),16(S)-tetramethyl-19-trityloxynonadeca-11,17-dien-3(R)-ol

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Chemical Property of 13(S),15(S)-bis(tert-butyldimethylsilanyloxy)-2(S)-[2(S)-(4-methoxyphenyl)-5(S)-methyl[1,3]dioxan-4(S)-yl]-9(R)-(4-methoxybenzyloxy)-6(R),8(S),10(S),16(S)-tetramethyl-19-trityloxynonadeca-11,17-dien-3(R)-ol

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Technology Process of 13(S),15(S)-bis(tert-butyldimethylsilanyloxy)-2(S)-[2(S)-(4-methoxyphenyl)-5(S)-methyl[1,3]dioxan-4(S)-yl]-9(R)-(4-methoxybenzyloxy)-6(R),8(S),10(S),16(S)-tetramethyl-19-trityloxynonadeca-11,17-dien-3(R)-ol

There total 24 articles about 13(S),15(S)-bis(tert-butyldimethylsilanyloxy)-2(S)-[2(S)-(4-methoxyphenyl)-5(S)-methyl[1,3]dioxan-4(S)-yl]-9(R)-(4-methoxybenzyloxy)-6(R),8(S),10(S),16(S)-tetramethyl-19-trityloxynonadeca-11,17-dien-3(R)-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: 71.0%

: 672296-47-8
13(S),15(S)-bis(tert-butyldimethylsilanyloxy)-2(S)-[2(S)-(4-methoxyphenyl)-5(S)-methyl[1,3]dioxan-4(S)-yl]-9(R)-(4-methoxybenzyloxy)-6(R),8(S),10(S),16(S)-tetramethyl-19-trityloxynonadeca-11,17-dien-3-one

: 951154-83-9
13(S),15(S)-bis(tert-butyldimethylsilanyloxy)-2(S)-[2(S)-(4-methoxyphenyl)-5(S)-methyl[1,3]dioxan-4(S)-yl]-9(R)-(4-methoxybenzyloxy)-6(R),8(S),10(S),16(S)-tetramethyl-19-trityloxynonadeca-11,17-dien-3(R)-ol

: 13(S),15(S)-bis(tert-butyldimethylsilanyloxy)-2(S)-[2(S)-(4-methoxyphenyl)-5(S)-methyl[1,3]dioxan-4(S)-yl]-9(R)-(4-methoxybenzyloxy)-6(R),8(S),10(S),16(S)-tetramethyl-19-trityloxynonadeca-11,17-dien-3(S)-ol

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; for 2h;
DOI:10.1016/j.tet.2007.05.033

Reference yield:

: 672296-45-6
{3(R)-[2(S)-(4-methoxyphenyl)-5(S)-methyl[1,3]dioxan-4(S)-yl]-2-oxobutyl}phosphonic acid dimethyl ester

: 951154-83-9
13(S),15(S)-bis(tert-butyldimethylsilanyloxy)-2(S)-[2(S)-(4-methoxyphenyl)-5(S)-methyl[1,3]dioxan-4(S)-yl]-9(R)-(4-methoxybenzyloxy)-6(R),8(S),10(S),16(S)-tetramethyl-19-trityloxynonadeca-11,17-dien-3(R)-ol

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 0.34 g / tetrahydrofuran; H₂O / 12 h

2.1: 89 percent / NiCl₂*6H₂O; NaBH₄ / methanol; tetrahydrofuran / 0 °C

3.1: 71 percent / NaBH₄ / methanol / 2 h / 0 °C

With barium dihydroxide; sodium tetrahydroborate; nickel dichloride; In tetrahydrofuran; methanol; 1.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2007.05.033

Reference yield:

: C₁₁H₂₀O₅

: 951154-83-9
13(S),15(S)-bis(tert-butyldimethylsilanyloxy)-2(S)-[2(S)-(4-methoxyphenyl)-5(S)-methyl[1,3]dioxan-4(S)-yl]-9(R)-(4-methoxybenzyloxy)-6(R),8(S),10(S),16(S)-tetramethyl-19-trityloxynonadeca-11,17-dien-3(R)-ol

Guidance literature:: Multi-step reaction with 19 steps

1.1: 2.96 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

2.1: 65 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 20 °C

3.1: 93 percent / Dess-Martin periodinane / CH₂Cl₂ / 1 h

4.1: NaHMDS / tetrahydrofuran / -78 - 20 °C

4.2: 75 percent / tetrahydrofuran / -78 - 20 °C

5.1: aq. KOH / ethanol; tetrahydrofuran / 6 h / Heating

6.1: Et₃N / tetrahydrofuran / 0.25 h / -10 °C

6.2: 1.79 g / NaBH₄ / tetrahydrofuran; H₂O / 0 °C

7.1: 99 percent / 4-(dimethylamino)pyridine; pyridine / 18 h / Heating

8.1: 74 percent / diisobutylaluminum hydride / hexane; CH₂Cl₂ / -78 - 0 °C

9.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

10.1: potassium tert-butoxide / tetrahydrofuran / 0.5 h / -78 °C

10.2: 2.01 g / tetrahydrofuran / 3 h / -78 - 0 °C

11.1: 97 percent / NiCl₂*6H₂O; NaBH₄ / methanol; tetrahydrofuran / 0 °C

12.1: aq. KOH / ethanol; tetrahydrofuran / 6 h / Heating

13.1: Et₃N / tetrahydrofuran / -78 - 0 °C

13.2: 1.52 g / LiCl / tetrahydrofuran / 0 - 20 °C

14.1: NaHMDS / tetrahydrofuran / 0.5 h / -78 °C

14.2: 62 percent / tetrahydrofuran / 4 h / -78 °C

15.1: 87 percent / LiBH₄ / methanol; tetrahydrofuran / 2 h / 0 °C

16.1: Dess-Martin periodinane / CH₂Cl₂ / 1 h

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

17.2: 0.34 g / tetrahydrofuran; H₂O / 12 h

18.1: 89 percent / NiCl₂*6H₂O; NaBH₄ / methanol; tetrahydrofuran / 0 °C

19.1: 71 percent / NaBH₄ / methanol / 2 h / 0 °C

With pyridine; 2,6-dimethylpyridine; dmap; barium dihydroxide; potassium hydroxide; sodium tetrahydroborate; lithium borohydride; potassium tert-butylate; sodium hexamethyldisilazane; diisobutylaluminium hydride; Dess-Martin periodane; pyridine hydrogenfluoride; triethylamine; nickel dichloride; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; 3.1: Dess-Martin oxidation / 4.2: Wittig coupling / 9.1: Dess-Martin oxidation / 10.2: Horner-Wadsworth-Emmons reaction / 16.1: Dess-Martin oxidation / 17.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2007.05.033