Technology Process of 2H-Pyran-2-ol,
6-[(2S)-3-[(2R,4R,6S)-4-(acetyloxy)tetrahydro-6-[2-[(4-methoxyphenyl)
methoxy]ethyl]-2H-pyran-2-yl]-2-methoxypropyl]tetrahydro-5-methyl-,
acetate, (5S,6R)-
There total 13 articles about 2H-Pyran-2-ol,
6-[(2S)-3-[(2R,4R,6S)-4-(acetyloxy)tetrahydro-6-[2-[(4-methoxyphenyl)
methoxy]ethyl]-2H-pyran-2-yl]-2-methoxypropyl]tetrahydro-5-methyl-,
acetate, (5S,6R)- 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:
- Guidance literature:
-
Multi-step reaction with 7 steps
1.1: (R,R)-1,2-bis-p-toluenesulfonylamino-1,2-diphenylethane; boron tribromide / CH2Cl2 / 16 h / 20 °C
1.2: CH2Cl2 / 2 h / -78 °C
2.1: 77 percent / bis(trifluoroacetoxy)iodobenzene / 0.08 h / 20 °C
3.1: 88 percent / molecular sieves 4 Angstroem; Proton Sponge (R) / CH2Cl2 / 8 h / 0 - 20 °C
4.1: 88 percent / 4-methylmorpholine N-oxide; OsO4 / acetone; H2O / 2 h / 20 °C
5.1: LiAlH4; (+)-N-methylephedrine; N-ethylaniline / diethyl ether / 3 h / -78 °C
6.1: H3PO4 / tetrahydrofuran; H2O / 2 h / 20 °C
7.1: 68 mg / pyridine; 4-(dimethylamino)pyridine / CH2Cl2 / 2 h
With
pyridine; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; Proton Sponge; phosphoric acid; 4 A molecular sieve; boron tribromide; (+)-N-methylephedrine; 4-methyl-N-((1R,2R)-2-{[(4-methylphenyl)sulfonyl]amino}-1,2-diphenylethyl)benzenesulfonamide; 4-methylmorpholine N-oxide; N-ethyl-N-phenylamine; bis-[(trifluoroacetoxy)iodo]benzene;
In
tetrahydrofuran; diethyl ether; dichloromethane; water; acetone;
DOI:10.1021/ol036071v
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: 81 percent / dicyclohexylcarbodiimide*iodomethane complex / tetrahydrofuran / 12 h / 40 °C
2.1: n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -30 - -20 °C
2.2: 95 percent / hexane; tetrahydrofuran / -78 - 0 °C
3.1: propylene oxide; N-bromosuccinimide / dimethylformamide; CH2Cl2 / 6 h / -78 °C
4.1: lithium diisopropylamide; tributyltin hydride; CuBr*Me2S / tetrahydrofuran / 0.5 h / -78 - -40 °C
4.2: (R,R)-1,2-bis-para-toluenesulfonylamino-1,2-diphenylethane; boron tribromide / CH2Cl2 / 16 h / 20 °C
4.3: CH2Cl2 / 2 h / -78 °C
5.1: 77 percent / bis(trifluoroacetoxy)iodobenzene / 0.08 h / 20 °C
6.1: 88 percent / molecular sieves 4 Angstroem; Proton Sponge (R) / CH2Cl2 / 8 h / 0 - 20 °C
7.1: 88 percent / 4-methylmorpholine N-oxide; OsO4 / acetone; H2O / 2 h / 20 °C
8.1: LiAlH4; (+)-N-methylephedrine; N-ethylaniline / diethyl ether / 3 h / -78 °C
9.1: H3PO4 / tetrahydrofuran; H2O / 2 h / 20 °C
10.1: 68 mg / pyridine; 4-(dimethylamino)pyridine / CH2Cl2 / 2 h
With
pyridine; dmap; N-Bromosuccinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; N,N'-dicyclohexyl-carbodiimidium iodide; Proton Sponge; copper(I) bromide dimethylsulfide complex; phosphoric acid; 4 A molecular sieve; tri-n-butyl-tin hydride; (+)-N-methylephedrine; 4-methylmorpholine N-oxide; N-ethyl-N-phenylamine; bis-[(trifluoroacetoxy)iodo]benzene; methyloxirane; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ol036071v
- Guidance literature:
-
Multi-step reaction with 9 steps
1.1: n-butyllithium / hexane; tetrahydrofuran / 1.5 h / -30 - -20 °C
1.2: 95 percent / hexane; tetrahydrofuran / -78 - 0 °C
2.1: propylene oxide; N-bromosuccinimide / dimethylformamide; CH2Cl2 / 6 h / -78 °C
3.1: lithium diisopropylamide; tributyltin hydride; CuBr*Me2S / tetrahydrofuran / 0.5 h / -78 - -40 °C
3.2: (R,R)-1,2-bis-para-toluenesulfonylamino-1,2-diphenylethane; boron tribromide / CH2Cl2 / 16 h / 20 °C
3.3: CH2Cl2 / 2 h / -78 °C
4.1: 77 percent / bis(trifluoroacetoxy)iodobenzene / 0.08 h / 20 °C
5.1: 88 percent / molecular sieves 4 Angstroem; Proton Sponge (R) / CH2Cl2 / 8 h / 0 - 20 °C
6.1: 88 percent / 4-methylmorpholine N-oxide; OsO4 / acetone; H2O / 2 h / 20 °C
7.1: LiAlH4; (+)-N-methylephedrine; N-ethylaniline / diethyl ether / 3 h / -78 °C
8.1: H3PO4 / tetrahydrofuran; H2O / 2 h / 20 °C
9.1: 68 mg / pyridine; 4-(dimethylamino)pyridine / CH2Cl2 / 2 h
With
pyridine; dmap; N-Bromosuccinimide; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; Proton Sponge; copper(I) bromide dimethylsulfide complex; phosphoric acid; 4 A molecular sieve; tri-n-butyl-tin hydride; (+)-N-methylephedrine; 4-methylmorpholine N-oxide; N-ethyl-N-phenylamine; bis-[(trifluoroacetoxy)iodo]benzene; methyloxirane; lithium diisopropyl amide;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ol036071v