(6S,8R,9S)-6-amino>-9-benzyloxy-8-<(benzyloxy)carbonyl>oxytridecan-2-one

Base Information

Chemical Name:(6S,8R,9S)-6-amino>-9-benzyloxy-8-<(benzyloxy)carbonyl>oxytridecan-2-one
CAS No.:131447-07-9
Molecular Formula:C₄₃H₅₁NO₇
Molecular Weight:693.88
Hs Code.:

(6S,8R,9S)-6-<N-Benzyl-N-<(benzyloxy)carbonyl>amino>-9-benzyloxy-8-<(benzyloxy)carbonyl>oxytridecan-2-one

Synonyms:(6S,8R,9S)-6-amino>-9-benzyloxy-8-<(benzyloxy)carbonyl>oxytridecan-2-one

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Chemical Property of (6S,8R,9S)-6-amino>-9-benzyloxy-8-<(benzyloxy)carbonyl>oxytridecan-2-one

Chemical Property:

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Technology Process of (6S,8R,9S)-6-amino>-9-benzyloxy-8-<(benzyloxy)carbonyl>oxytridecan-2-one

There total 13 articles about (6S,8R,9S)-6-amino>-9-benzyloxy-8-<(benzyloxy)carbonyl>oxytridecan-2-one 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:

: 84379-53-3
2-O-benzyl-3,4-O-isopropylidene-L-threitol

: 131447-07-9
(6S,8R,9S)-6-amino>-9-benzyloxy-8-<(benzyloxy)carbonyl>oxytridecan-2-one

Guidance literature:: Multi-step reaction with 13 steps

1: 97 percent / N,N-dimethylaminopyridine / CH₂Cl₂ / 2 h

2: 87 percent / Li₂CuCl₄ / tetrahydrofuran / 1) -78 deg C, 1.5 h, 2) room temp., 65 h

3: 98 percent / 6N HCl / methanol / 1 h / 55 °C

4: 1.5 h / 70 °C

5: acetic anhydride / 1 h / Heating

6: 57 percent / toluene / 14 h / Heating

7: 96 percent / LiAlH₄ / diethyl ether / 14 h / Ambient temperature

8: 97 percent / N,N-dimethylaminopyridine, diisopropylethylamine / CH₂Cl₂ / 1.5 h / Ambient temperature

9: 80 percent / NaI / butan-2-one / 5.5 h / 75 °C

10: 1) (2-thienyl)Cu(CN)Li / 1) THF, a) -78 deg C, 15 min, b) 0 deg C, 1.5 h, 2) a) -78 deg C, 15 min, b) 0 deg C, 1.5 h, c) room temp., 18 h

11: 90 percent / Zn dust, AcOH / H₂O; tetrahydrofuran / 2.5 h / 60 °C

12: 79 percent / 3.5 N Na₂CO₃ / CH₂Cl₂ / 1) 0 deg C, 30 min, 2) room temp., 2.5 h

13: 91 percent / O₂ / PdCl₂, CuCl₂ / dimethylformamide; H₂O / 50 °C

With hydrogenchloride; dmap; lithium aluminium tetrahydride; dilithium tetrachlorocuprate; oxygen; acetic anhydride; sodium carbonate; acetic acid; thien-2-yl(cyano)copper lithium; N-ethyl-N,N-diisopropylamine; sodium iodide; zinc; copper dichloride; palladium dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; butanone;
DOI:10.1016/S0040-4020(01)80881-4

Reference yield:

: 131446-96-3
(S)-2-(benzyloxy)-2-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)ethyl 4-methylbenzenesulfonate

: 131447-07-9
(6S,8R,9S)-6-amino>-9-benzyloxy-8-<(benzyloxy)carbonyl>oxytridecan-2-one

Guidance literature:: Multi-step reaction with 12 steps

1: 87 percent / Li₂CuCl₄ / tetrahydrofuran / 1) -78 deg C, 1.5 h, 2) room temp., 65 h

2: 98 percent / 6N HCl / methanol / 1 h / 55 °C

3: 1.5 h / 70 °C

4: acetic anhydride / 1 h / Heating

5: 57 percent / toluene / 14 h / Heating

6: 96 percent / LiAlH₄ / diethyl ether / 14 h / Ambient temperature

7: 97 percent / N,N-dimethylaminopyridine, diisopropylethylamine / CH₂Cl₂ / 1.5 h / Ambient temperature

8: 80 percent / NaI / butan-2-one / 5.5 h / 75 °C

9: 1) (2-thienyl)Cu(CN)Li / 1) THF, a) -78 deg C, 15 min, b) 0 deg C, 1.5 h, 2) a) -78 deg C, 15 min, b) 0 deg C, 1.5 h, c) room temp., 18 h

10: 90 percent / Zn dust, AcOH / H₂O; tetrahydrofuran / 2.5 h / 60 °C

11: 79 percent / 3.5 N Na₂CO₃ / CH₂Cl₂ / 1) 0 deg C, 30 min, 2) room temp., 2.5 h

12: 91 percent / O₂ / PdCl₂, CuCl₂ / dimethylformamide; H₂O / 50 °C

With hydrogenchloride; dmap; lithium aluminium tetrahydride; dilithium tetrachlorocuprate; oxygen; acetic anhydride; sodium carbonate; acetic acid; thien-2-yl(cyano)copper lithium; N-ethyl-N,N-diisopropylamine; sodium iodide; zinc; copper dichloride; palladium dichloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; butanone;
DOI:10.1016/S0040-4020(01)80881-4

Reference yield:

: 131447-04-6
<3S,5R,5(1S)>-N-Benzyl-5-<1-(benzyloxy)pentyl>-3-(4-pentenyl)isoxazolidine

: 131447-07-9
(6S,8R,9S)-6-amino>-9-benzyloxy-8-<(benzyloxy)carbonyl>oxytridecan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / Zn dust, AcOH / H₂O; tetrahydrofuran / 2.5 h / 60 °C

2: 79 percent / 3.5 N Na₂CO₃ / CH₂Cl₂ / 1) 0 deg C, 30 min, 2) room temp., 2.5 h

3: 91 percent / O₂ / PdCl₂, CuCl₂ / dimethylformamide; H₂O / 50 °C

With oxygen; sodium carbonate; acetic acid; zinc; copper dichloride; palladium dichloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/S0040-4020(01)80881-4