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

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Chemical Name: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
CAS No.:296795-24-9
Molecular Formula:C₄₄H₇₀N₂O₆Si₂
Molecular Weight:779.221
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 26 articles about 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 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: 78.0%

: 7341-97-1
N-phenyl propynamide

: 296795-23-8
((2R,6R)-4-methylene-6-(((2R,4S,6R)-4-(triisopropylsilyloxy)-6-(2-(triisopropylsilyloxy)methyl-1,3-oxazol-4-yl)tetrahydro-2H-pyran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)methyl trifluoromethanesulfonate

: 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

Guidance literature:: N-phenyl propynamide; With n-butyllithium; In tetrahydrofuran; at -20 ℃;

((2R,6R)-4-methylene-6-(((2R,4S,6R)-4-(triisopropylsilyloxy)-6-(2-(triisopropylsilyloxy)methyl-1,3-oxazol-4-yl)tetrahydro-2H-pyran-2-yl)methyl)tetrahydro-2H-pyran-2-yl)methyl trifluoromethanesulfonate; In tetrahydrofuran;
DOI:10.1002/1521-3773(20000717)39:14<2536::AID-ANIE2536>3.0.CO;2-U

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 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

Guidance literature:: Multi-step reaction with 16 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

With pyridine; 1H-imidazole; 2,6-dimethylpyridine; triethylsilane; dmap; lithium borohydride; n-butyllithium; oxalyl dichloride; di-n-butylboryl trifluoromethanesulfonate; boron trifluoride diethyl etherate; 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

Reference yield:

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

: 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

Guidance literature:: Multi-step reaction with 10 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

With pyridine; 2,6-dimethylpyridine; triethylsilane; n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; boron trifluoride diethyl etherate; 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