(R)-1-((2R,4R,6S)-6-(((2R,4R,6R)-6-((R)-2-hydroxypent-4-en-1-yl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)heptadecan-2-yl acetate

Base Information

• Chemical Name: (R)-1-((2R,4R,6S)-6-(((2R,4R,6R)-6-((R)-2-hydroxypent-4-en-1-yl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)heptadecan-2-yl acetate
• CAS No.: 1443040-69-4
• Molecular Formula: C₄₅H₆₈O₇
• Molecular Weight: 721.031
• Mol file: 1443040-69-4.mol

Synonyms:(R)-1-((2R,4R,6S)-6-(((2R,4R,6R)-6-((R)-2-hydroxypent-4-en-1-yl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)heptadecan-2-yl acetate

Chemical Property of (R)-1-((2R,4R,6S)-6-(((2R,4R,6R)-6-((R)-2-hydroxypent-4-en-1-yl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)heptadecan-2-yl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-((2R,4R,6S)-6-(((2R,4R,6R)-6-((R)-2-hydroxypent-4-en-1-yl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)heptadecan-2-yl acetate

There total 16 articles about (R)-1-((2R,4R,6S)-6-(((2R,4R,6R)-6-((R)-2-hydroxypent-4-en-1-yl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)heptadecan-2-yl acetate 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: 75.0%

(R)-1-((2R,4R,6S)-6-(((2S,4S,6S)-6-(2-oxoethyl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)heptadecan-2-yl acetate + (3aS,7aS)-1,3-bis[(4-bromophenyl)methyl]-2-chlorooctahydro-2-(2-propenyl)-1H-1,3,2-benzodiazasilole (547713-49-5) → (R)-1-((2R,4R,6S)-6-(((2R,4R,6R)-6-((R)-2-hydroxypent-4-en-1-yl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)heptadecan-2-yl acetate (1443040-69-4)

Guidance literature:

With scandium tris(trifluoromethanesulfonate); In dichloromethane; at -10 ℃; for 12h; diastereoselective reaction; Inert atmosphere;

DOI:10.1055/s-0035-1561607

Reference yield:

methyl 2-((2S,4S,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetate (1443040-52-5) → (R)-1-((2R,4R,6S)-6-(((2R,4R,6R)-6-((R)-2-hydroxypent-4-en-1-yl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)heptadecan-2-yl acetate (1443040-69-4)

Guidance literature:

Multi-step reaction with 12 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: diisobutylaluminium hydride / dichloromethane; hexane / -78 °C / Inert atmosphere

11.1: dmap; triethylamine / dichloromethane / 0.33 h / 0 °C

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

With 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; 2,3-dicyano-5,6-dichloro-p-benzoquinone; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; hexane; dichloromethane; 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) → (R)-1-((2R,4R,6S)-6-(((2R,4R,6R)-6-((R)-2-hydroxypent-4-en-1-yl)-2-phenyl-1,3-dioxan-4-yl)methyl)-2-phenyl-1,3-dioxan-4-yl)heptadecan-2-yl acetate (1443040-69-4)

Guidance literature:

Multi-step reaction with 12 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: diisobutylaluminium hydride / dichloromethane; hexane / -78 °C / Inert atmosphere

11.1: dmap; triethylamine / dichloromethane / 0.33 h / 0 °C

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

With 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; 2,3-dicyano-5,6-dichloro-p-benzoquinone; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; hexane; dichloromethane; 3.1: |Evans Aldol Reaction / 8.1: |Noyori Asymmetric Hydrogenation;

DOI:10.1055/s-0035-1561607

upstream raw materials:

(3aS,7aS)-1,3-bis[(4-bromophenyl)methyl]-2-chlorooctahydro-2-(2-propenyl)-1H-1,3,2-benzodiazasilole

benzaldehyde

(R)-1-((2S,4R,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-ol

methyl 2-((2S,4S,6S)-6-(2-((4-methoxybenzyl)oxy)ethyl)-2-phenyl-1,3-dioxan-4-yl)acetate

Downstream raw materials:

(R)-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-(((R)-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