(S)-1-((2S,4S,6R)-6-(((2R,4R,6R)-6-((R)-2-((tert-butyldimethylsilyl)oxy)heptadecyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-yl acrylate

Base Information

• Chemical Name: (S)-1-((2S,4S,6R)-6-(((2R,4R,6R)-6-((R)-2-((tert-butyldimethylsilyl)oxy)heptadecyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-yl acrylate
• CAS No.: 1443040-77-4
• Molecular Formula: C₅₂H₈₂O₇Si
• Molecular Weight: 847.304
• Mol file: 1443040-77-4.mol

Synonyms:(S)-1-((2S,4S,6R)-6-(((2R,4R,6R)-6-((R)-2-((tert-butyldimethylsilyl)oxy)heptadecyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-yl acrylate

Chemical Property of (S)-1-((2S,4S,6R)-6-(((2R,4R,6R)-6-((R)-2-((tert-butyldimethylsilyl)oxy)heptadecyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-yl acrylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-((2S,4S,6R)-6-(((2R,4R,6R)-6-((R)-2-((tert-butyldimethylsilyl)oxy)heptadecyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-yl acrylate

There total 17 articles about (S)-1-((2S,4S,6R)-6-(((2R,4R,6R)-6-((R)-2-((tert-butyldimethylsilyl)oxy)heptadecyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-yl acrylate 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: 64.0%

(S)-1-((2R,4R,6R)-6-(((2R,4R,6R)-6-((R)-2-((tert-butyldimethylsilyl)oxy)heptadecyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-ol (1443040-76-3) + acrylic acid (79-10-7) → (S)-1-((2S,4S,6R)-6-(((2R,4R,6R)-6-((R)-2-((tert-butyldimethylsilyl)oxy)heptadecyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-yl acrylate (1443040-77-4)

Guidance literature:

With dicyclohexyl-carbodiimide;

DOI:10.1021/ml4005039

Reference yield:

methyl 2-((2S,4S,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetate (1443040-52-5) → (S)-1-((2S,4S,6R)-6-(((2R,4R,6R)-6-((R)-2-((tert-butyldimethylsilyl)oxy)heptadecyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-yl acrylate (1443040-77-4)

Guidance literature:

Multi-step reaction with 13 steps

1.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere

1.2: 3 h / -78 - 20 °C / Inert atmosphere

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 3 h / 20 °C / Inert atmosphere

3.1: potassium tert-butylate / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

4.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 0 °C / Inert atmosphere

5.1: Dess-Martin periodane / dichloromethane / 2 h / 0 °C

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

6.2: 0.07 h / -78 - 20 °C / Inert atmosphere

7.1: Dess-Martin periodane / dichloromethane / 2 h / 0 °C

8.1: triethylamine; formic acid; ?chloro[(1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine]-(mesitylene) ruthenium (II) / 7 h / 0 - 20 °C

9.1: triethylamine; 2-nitrobenzenesulfonyl hydrazide / dichloromethane / 20 h / 20 °C

10.1: 1H-imidazole / N,N-dimethyl-formamide / 14 h / 20 °C

11.1: diisobutylaluminium hydride / dichloromethane; hexane / -78 °C / Inert atmosphere

12.1: scandium tris(trifluoromethanesulfonate) / dichloromethane / 12 h / -10 °C / Inert atmosphere

13.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 20 h / 20 °C

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; ?chloro[(1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine]-(mesitylene) ruthenium (II); n-butyllithium; formic acid; 2-nitrobenzenesulfonyl hydrazide; potassium tert-butylate; water; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 3.1: |Evans Aldol Reaction / 8.1: |Noyori Asymmetric Hydrogenation;

DOI:10.1055/s-0035-1561607

Reference yield:

2-((2S,4S,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetaldehyde (1443040-53-6) → (S)-1-((2S,4S,6R)-6-(((2R,4R,6R)-6-((R)-2-((tert-butyldimethylsilyl)oxy)heptadecyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-yl acrylate (1443040-77-4)

Guidance literature:

Multi-step reaction with 13 steps

1.1: scandium tris(trifluoromethanesulfonate) / dichloromethane / 12 h / -10 °C / Inert atmosphere

2.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 3 h / 20 °C / Inert atmosphere

3.1: potassium tert-butylate / tetrahydrofuran / 0.75 h / 0 °C / Inert atmosphere

4.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 0 °C / Inert atmosphere

5.1: Dess-Martin periodane / dichloromethane / 2 h / 0 °C

6.1: n-butyllithium / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere

6.2: 0.07 h / -78 - 20 °C / Inert atmosphere

7.1: Dess-Martin periodane / dichloromethane / 2 h / 0 °C

8.1: triethylamine; formic acid; ?chloro[(1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine]-(mesitylene) ruthenium (II) / 7 h / 0 - 20 °C

9.1: triethylamine; 2-nitrobenzenesulfonyl hydrazide / dichloromethane / 20 h / 20 °C

10.1: 1H-imidazole / N,N-dimethyl-formamide / 14 h / 20 °C

11.1: diisobutylaluminium hydride / dichloromethane; hexane / -78 °C / Inert atmosphere

12.1: scandium tris(trifluoromethanesulfonate) / dichloromethane / 12 h / -10 °C / Inert atmosphere

13.1: dicyclohexyl-carbodiimide; dmap / dichloromethane / 20 h / 20 °C

With 1H-imidazole; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; dmap; ?chloro[(1S,2S)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine]-(mesitylene) ruthenium (II); n-butyllithium; formic acid; 2-nitrobenzenesulfonyl hydrazide; potassium tert-butylate; water; diisobutylaluminium hydride; Dess-Martin periodane; triethylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 3.1: |Evans Aldol Reaction / 8.1: |Noyori Asymmetric Hydrogenation;

DOI:10.1055/s-0035-1561607

upstream raw materials:

(S)-1-((2R,4R,6R)-6-(((2R,4R,6R)-6-((R)-2-((tert-butyldimethylsilyl)oxy)heptadecyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-ol

acrylic acid

ethyl 2-((2S,4S,6S)-6-(((2R,4R,6R)-6-((R)-2-((tert-butyldimethylsilyl)oxy)heptadecyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)acetate

2-((2S,4S,6S)-6-(((2R,4R,6R)-6-((R)-2-((tert-butyldimethylsilyl)oxy)heptadecyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)acetaldehyde

Downstream raw materials:

(S)-1-((2S,4S,6R)-6-(((2S,4S,6S)-6-((R)-2-hydroxyheptadecyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-yl acrylate

(S)-6-(((2S,4S,6R)-6-(((2R,4R,6R)-6-((R)-2-((tert-butyldimethylsilyl)oxy)heptadecyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-5,6-dihydro-2H-pyran-2-one

(S)-1-((2S,4S,6R)-6-(((2R,4S,6R)-6-((R)-2-acetoxyheptadecyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-yl acrylate

(R)-1-((2R,4R,6S)-6-(((2S,4R,6S)-6-(((S)-6-oxo-3,6-dihydro-2H-pyran-2-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)heptadecan-2-yl acetate