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

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Chemical Name: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
CAS No.:296795-37-4
Molecular Formula:C₃₅H₅₀N₂O₆Si
Molecular Weight:622.877
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 24 articles about 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 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%

: 296795-24-9
N-phenyl 4-((2R,6R)-4-methylene-6-(((2R,4S,6R)-4-(triisopropylsilyloxy)-6-(2-(triisopropyloxy)methyl-1,3-oxazol-4-yl)tetrahydro-2H-pyran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)but-2-yn-amide

: 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

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -78 - -50 ℃; for 1.33333h;
DOI:10.1021/ja002356g

Reference yield:

: 132629-37-9
ethyl 2-[(E)-2-phenylethenyl]oxazole-4-carboxylate

: 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

Guidance literature:: Multi-step reaction with 17 steps

1.1: 95 percent / DIBAlH / CH₂Cl₂ / 1 h / -91 °C

2.1: [Sn(S,S)-Ph-box)](OTf)2 / CH₂Cl₂ / 1 h / -78 °C

3.1: 100 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide / 1 h / 20 °C

4.1: potassium osmate dihydrate; potassium ferricyanide; potassium carbonate / quinoclidine; methanesulfonamide / 2-methyl-propan-2-ol; H₂O / 48 h / 20 °C

5.1: 19.8 g / lead tetraacetate; potassium carbonate / CH₂Cl₂ / 0.17 h / 0 °C

6.1: 95 percent / DIBAlH / CH₂Cl₂ / 0.5 h / -78 °C

7.1: 100 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

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

8.2: 82 percent / diethyl ether / 5 h / -105 °C

9.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

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

11.1: 96 percent / triethylsilane; boron trifluoride diethyl etherate / CH₂Cl₂ / 16.5 h / -78 - -50 °C

12.1: 90 percent / FeCl₃*SiO₂ / CHCl₃; acetone / 96 h / 20 °C

13.1: 100 percent / H₂ / Pd/C / propan-2-ol / 48 h / 760.05 Torr

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

14.2: 90 percent / tetrahydrofuran; cyclohexane; diethyl ether / 1 h

15.1: 100 percent / pyridine / CH₂Cl₂ / 0.33 h / -5 °C

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

16.2: 78 percent / tetrahydrofuran; hexane / 18 h / -20 °C

17.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.33 h / -78 - -50 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; lead(IV) acetate; triethylsilane; dmap; potassium osmate(VI); n-butyllithium; [Sn(S,S)-Ph-box)](OTf)2; di-n-butylboryl trifluoromethanesulfonate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; silica gel; iron(III) chloride; diisobutylaluminium hydride; potassium carbonate; pyridine hydrogenfluoride; phenyllithium; N-ethyl-N,N-diisopropylamine; potassium hexacyanoferrate(III); Quinuclidine; palladium on activated charcoal; methanesulfonamide; In tetrahydrofuran; pyridine; diethyl ether; hexane; dichloromethane; chloroform; cyclohexane; water; N,N-dimethyl-formamide; isopropyl alcohol; acetone; tert-butyl alcohol; 14.1: Wittig olefination;
DOI:10.1021/ja002356g

Reference yield:

: 181633-67-0
ethyl 2-hydroxymethyl-oxazole-4-carboxylate

: 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

Guidance literature:: Multi-step reaction with 17 steps

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

2.1: 97 percent / DIBALH / CH₂Cl₂ / 1 h / -94 °C

3.1: triethylamine; di-n-butylboron trifluoromethanesulfonate / CH₂Cl₂ / 1 h / 20 °C

3.2: CH₂Cl₂ / 50 h / -78 - -40 °C

4.1: 91 percent / Zn; AcOH / tetrahydrofuran / 0.25 h / 20 °C

5.1: 100 percent / imidazole; 4-(dimethylamino)pyridine / dimethylformamide / 1 h / 20 °C

6.1: 85 percent / lithium borohydride; H₂O / diethyl ether; tetrahydrofuran / 0.5 h / 20 °C

7.1: 99 percent / oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 2.5 h / -78 °C

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

8.2: 82 percent / diethyl ether / 5 h / -105 °C

9.1: 99 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 °C

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

11.1: 96 percent / triethylsilane; boron trifluoride diethyl etherate / CH₂Cl₂ / 16.5 h / -78 - -50 °C

12.1: 90 percent / FeCl₃*SiO₂ / CHCl₃; acetone / 96 h / 20 °C

13.1: 100 percent / H₂ / Pd/C / propan-2-ol / 48 h / 760.05 Torr

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

14.2: 90 percent / tetrahydrofuran; cyclohexane; diethyl ether / 1 h

15.1: 100 percent / pyridine / CH₂Cl₂ / 0.33 h / -5 °C

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

16.2: 78 percent / tetrahydrofuran; hexane / 18 h / -20 °C

17.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.33 h / -78 - -50 °C

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; triethylsilane; dmap; lithium borohydride; n-butyllithium; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; hydrogen; silica gel; iron(III) chloride; diisobutylaluminium hydride; pyridine hydrogenfluoride; acetic acid; dimethyl sulfoxide; phenyllithium; triethylamine; N-ethyl-N,N-diisopropylamine; zinc; palladium on activated charcoal; In tetrahydrofuran; pyridine; diethyl ether; hexane; dichloromethane; chloroform; cyclohexane; N,N-dimethyl-formamide; isopropyl alcohol; acetone; 7.1: Swern oxidation / 14.1: Wittig olefination;
DOI:10.1021/ja002356g