N-phenyl 4-((2R,6R)-4-methylene-6-(((2R,4S,6R)-4-(triisopropylsilyloxy)-6-(2-(methanesulfonylmethyl)-1,3-oxazol-4-yl)tetrahydro-2H-pyran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)but-2-ynamide

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Chemical Name:N-phenyl 4-((2R,6R)-4-methylene-6-(((2R,4S,6R)-4-(triisopropylsilyloxy)-6-(2-(methanesulfonylmethyl)-1,3-oxazol-4-yl)tetrahydro-2H-pyran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)but-2-ynamide
CAS No.:296795-25-0
Molecular Formula:C₃₆H₅₂N₂O₈SSi
Molecular Weight:700.969
Hs Code.:

N-phenyl 4-((2R,6R)-4-methylene-6-(((2R,4S,6R)-4-(triisopropylsilyloxy)-6-(2-(methanesulfonylmethyl)-1,3-oxazol-4-yl)tetrahydro-2H-pyran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)but-2-ynamide

Synonyms:N-phenyl 4-((2R,6R)-4-methylene-6-(((2R,4S,6R)-4-(triisopropylsilyloxy)-6-(2-(methanesulfonylmethyl)-1,3-oxazol-4-yl)tetrahydro-2H-pyran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)but-2-ynamide

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Chemical Property of N-phenyl 4-((2R,6R)-4-methylene-6-(((2R,4S,6R)-4-(triisopropylsilyloxy)-6-(2-(methanesulfonylmethyl)-1,3-oxazol-4-yl)tetrahydro-2H-pyran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)but-2-ynamide

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Technology Process of N-phenyl 4-((2R,6R)-4-methylene-6-(((2R,4S,6R)-4-(triisopropylsilyloxy)-6-(2-(methanesulfonylmethyl)-1,3-oxazol-4-yl)tetrahydro-2H-pyran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)but-2-ynamide

There total 29 articles about N-phenyl 4-((2R,6R)-4-methylene-6-(((2R,4S,6R)-4-(triisopropylsilyloxy)-6-(2-(methanesulfonylmethyl)-1,3-oxazol-4-yl)tetrahydro-2H-pyran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)but-2-ynamide 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%

: 124-63-0
methanesulfonyl chloride

: 296795-37-4
N-phenyl 4-((2R,6R)-4-methylene-6-(((2R,4S,6R)-4-(triisopropylsilyloxy)-6-(2-(hydroxymethyl)-1,3-oxazol-4-yl)tetrahydro-2H-pyran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)but-2-ynamide

: 296795-25-0
N-phenyl 4-((2R,6R)-4-methylene-6-(((2R,4S,6R)-4-(triisopropylsilyloxy)-6-(2-(methanesulfonylmethyl)-1,3-oxazol-4-yl)tetrahydro-2H-pyran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)but-2-ynamide

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -5 ℃; for 0.333333h;
DOI:10.1021/ja002356g

Reference yield:

: 296795-35-2
(3R)-3-(2-hydroxymethyl-1,3-oxazol-4-yl)-3-(triethylsilyloxy)propanal

: 296795-25-0
N-phenyl 4-((2R,6R)-4-methylene-6-(((2R,4S,6R)-4-(triisopropylsilyloxy)-6-(2-(methanesulfonylmethyl)-1,3-oxazol-4-yl)tetrahydro-2H-pyran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)but-2-ynamide

Guidance literature:: Multi-step reaction with 12 steps

1.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

2.1: diisopropylethylamine; di-n-butylboron trifluoromethanesulfonate / CH₂Cl₂ / 0.5 h / -78 °C

2.2: 82 percent / diethyl ether / 5 h / -105 °C

3.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

4.1: pyridinium hydrofluoride; H₂O / tetrahydrofuran; pyridine / 3 h / 0 °C

5.1: 96 percent / triethylsilane; boron trifluoride diethyl etherate / CH₂Cl₂ / 16.5 h / -78 - -50 °C

6.1: 90 percent / FeCl₃*SiO₂ / CHCl₃; acetone / 96 h / 20 °C

7.1: 100 percent / H₂ / Pd/C / propan-2-ol / 48 h / 760.05 Torr

8.1: PhLi / tetrahydrofuran; cyclohexane; diethyl ether / 2 h / 20 °C

8.2: 90 percent / tetrahydrofuran; cyclohexane; diethyl ether / 1 h

9.1: 100 percent / pyridine / CH₂Cl₂ / 0.33 h / -5 °C

10.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C

10.2: 78 percent / tetrahydrofuran; hexane / 18 h / -20 °C

11.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.33 h / -78 - -50 °C

12.1: 99 percent / diisopropylethylamine / CH₂Cl₂ / 0.33 h / -5 °C

With pyridine; 2,6-dimethylpyridine; triethylsilane; n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; silica gel; iron(III) chloride; pyridine hydrogenfluoride; phenyllithium; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; diethyl ether; hexane; dichloromethane; chloroform; cyclohexane; isopropyl alcohol; acetone; 8.1: Wittig olefination;
DOI:10.1021/ja002356g

Reference yield:

: 296795-19-2
(3R)-3-(2-formyl-1,3-oxazol-4-yl)-3-(triethylsilyloxy)-thiopropionic acid S-tert-butyl ester

: 296795-25-0
N-phenyl 4-((2R,6R)-4-methylene-6-(((2R,4S,6R)-4-(triisopropylsilyloxy)-6-(2-(methanesulfonylmethyl)-1,3-oxazol-4-yl)tetrahydro-2H-pyran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)but-2-ynamide

Guidance literature:: Multi-step reaction with 13 steps

1.1: 95 percent / DIBAlH / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

3.1: diisopropylethylamine; di-n-butylboron trifluoromethanesulfonate / CH₂Cl₂ / 0.5 h / -78 °C

3.2: 82 percent / diethyl ether / 5 h / -105 °C

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

5.1: pyridinium hydrofluoride; H₂O / tetrahydrofuran; pyridine / 3 h / 0 °C

6.1: 96 percent / triethylsilane; boron trifluoride diethyl etherate / CH₂Cl₂ / 16.5 h / -78 - -50 °C

7.1: 90 percent / FeCl₃*SiO₂ / CHCl₃; acetone / 96 h / 20 °C

8.1: 100 percent / H₂ / Pd/C / propan-2-ol / 48 h / 760.05 Torr

9.1: PhLi / tetrahydrofuran; cyclohexane; diethyl ether / 2 h / 20 °C

9.2: 90 percent / tetrahydrofuran; cyclohexane; diethyl ether / 1 h

10.1: 100 percent / pyridine / CH₂Cl₂ / 0.33 h / -5 °C

11.1: n-BuLi / tetrahydrofuran; hexane / 1 h / 0 °C

11.2: 78 percent / tetrahydrofuran; hexane / 18 h / -20 °C

12.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.33 h / -78 - -50 °C

13.1: 99 percent / diisopropylethylamine / CH₂Cl₂ / 0.33 h / -5 °C

With pyridine; 2,6-dimethylpyridine; triethylsilane; n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; silica gel; iron(III) chloride; diisobutylaluminium hydride; pyridine hydrogenfluoride; phenyllithium; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; In tetrahydrofuran; pyridine; diethyl ether; hexane; dichloromethane; chloroform; cyclohexane; isopropyl alcohol; acetone; 9.1: Wittig olefination;
DOI:10.1021/ja002356g