(2S,4S,5S)-4-((2R,3S,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,3S,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.: 871236-59-8
• Molecular Formula: C₇₈H₁₂₈O₈Si₄
• Molecular Weight: 1306.21

Synonyms:(2S,4S,5S)-4-((2R,3S,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

Chemical Property of (2S,4S,5S)-4-((2R,3S,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

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,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 46 articles about (2S,4S,5S)-4-((2R,3S,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: 97.0%

(2S,3S,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 (792921-86-9) + t-butyldimethylsiyl triflate (69739-34-0) → (2S,4S,5S)-4-((2R,3S,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 (871236-59-8)

Guidance literature:

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

DOI:10.1016/j.tet.2007.05.033

Reference yield:

(-)-(R)-4-benzyl-3-((2R,3S,4S)-3-((tert-butyldimethylsilyl)oxy)-5-((4-methoxybenzyl)oxy)-2,4-dimethylpentanoyl)oxazolidin-2-one (443761-65-7) → (2S,4S,5S)-4-((2R,3S,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 (871236-59-8)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 90 percent / LiBH₄ / methanol; tetrahydrofuran / 1.75 h / 0 - 20 °C

2.1: imidazole; ethyldiisopropylamine; iodine / PPh₃ / benzene; diethyl ether; acetonitrile / 0.5 h / 20 °C

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

3.2: 87 percent / tetrahydrofuran; hexane / 24 h / 20 °C

4.1: 96 percent / LDA; borane*ammonia complex / tetrahydrofuran; hexane / -78 - 20 °C

5.1: 95 percent / imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 20 °C

6.1: 98 percent / DDQ; aq. phosphate buffer / CH₂Cl₂ / 1 h / 20 °C / pH 7

7.1: sulfur trioxide*pyridine complex; Et₃N; DMSO / CH₂Cl₂ / 1 h / 0 °C

8.1: PPh₃ / CH₂Cl₂ / 0.17 h / 0 °C

8.2: 4.76 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

9.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

9.2: 95 percent / aq. NH₄Cl / tetrahydrofuran; hexane

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

10.2: 93 percent / tetrahydrofuran; hexane / -78 - 0 °C

11.1: 79 percent / i-PrOH / (S,S)-Noyori catalyst

12.1: 91 percent / hydrogen / Lindlar catalyst / toluene / 1 h

13.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

14.1: 67 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 21 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: 2.60 g / tetrahydrofuran; H₂O / 12 h

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

18.1: 28 percent / NaBH₄ / methanol / 2 h / 0 °C

19.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; barium dihydroxide; sodium tetrahydroborate; lithium borohydride; n-butyllithium; phosphate buffer; hydrogen; iodine; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; isopropyl alcohol; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; nickel dichloride; lithium diisopropyl amide; Lindlar's catalyst; (S,S)-Noyori catalyst; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; acetonitrile; benzene; 3.2: Meyers asymmetric alkylation / 9.1: Corey-Fuchs reaction / 15.1: Dess-Martin oxidation / 16.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.tet.2007.05.033

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (2S,4S,5S)-4-((2R,3S,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 (871236-59-8)

Guidance literature:

Multi-step reaction with 20 steps

1.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

2.1: 90 percent / LiBH₄ / methanol; tetrahydrofuran / 1.75 h / 0 - 20 °C

3.1: imidazole; ethyldiisopropylamine; iodine / PPh₃ / benzene; diethyl ether; acetonitrile / 0.5 h / 20 °C

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

4.2: 87 percent / tetrahydrofuran; hexane / 24 h / 20 °C

5.1: 96 percent / LDA; borane*ammonia complex / tetrahydrofuran; hexane / -78 - 20 °C

6.1: 95 percent / imidazole; 4-(dimethylamino)pyridine / CH₂Cl₂ / 2 h / 20 °C

7.1: 98 percent / DDQ; aq. phosphate buffer / CH₂Cl₂ / 1 h / 20 °C / pH 7

8.1: sulfur trioxide*pyridine complex; Et₃N; DMSO / CH₂Cl₂ / 1 h / 0 °C

9.1: PPh₃ / CH₂Cl₂ / 0.17 h / 0 °C

9.2: 4.76 g / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

10.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

10.2: 95 percent / aq. NH₄Cl / tetrahydrofuran; hexane

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

11.2: 93 percent / tetrahydrofuran; hexane / -78 - 0 °C

12.1: 79 percent / i-PrOH / (S,S)-Noyori catalyst

13.1: 91 percent / hydrogen / Lindlar catalyst / toluene / 1 h

14.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

15.1: 67 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 21 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: 2.60 g / tetrahydrofuran; H₂O / 12 h

18.1: 76 percent / NiCl₂*6H₂O; NaBH₄ / methanol; tetrahydrofuran / 0 °C

19.1: 28 percent / NaBH₄ / methanol / 2 h / 0 °C

20.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0 - 20 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; dmap; barium dihydroxide; sodium tetrahydroborate; lithium borohydride; n-butyllithium; phosphate buffer; hydrogen; iodine; Dess-Martin periodane; pyridine hydrogenfluoride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; isopropyl alcohol; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; nickel dichloride; lithium diisopropyl amide; Lindlar's catalyst; (S,S)-Noyori catalyst; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; toluene; acetonitrile; benzene; 4.2: Meyers asymmetric alkylation / 10.1: Corey-Fuchs reaction / 16.1: Dess-Martin oxidation / 17.2: Horner-Wadsworth-Emmons reaction;

DOI:10.1016/j.tet.2007.05.033

upstream raw materials:

(2S,3S,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

t-butyldimethylsiyl triflate

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

ethyl (4S,5R,6S,2E)-7-(4-methoxybenzyloxy)-5-(tert-butyldimethylsilyloxy)-4,6-dimethylhept-2-enoate

Downstream raw materials:

(2S,3S,4R,5S,8S,10S,11R,12S,13Z,15S,17S,18R,19E)-3-(4-methoxybenzyloxy)-5,11,15,17-tetrakis(tert-butyldimethylsilyloxy)-2,4,8,10,12,18-hexamethyl-21-trityloxyhenicosa-13,19-dien-1-ol

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