(6S,8R,9S)-6-(Dibenzylamino)-9-(benzyloxy)-2,2-ethylenedioxy-8-hydroxytridecane

Base Information

Chemical Name:(6S,8R,9S)-6-(Dibenzylamino)-9-(benzyloxy)-2,2-ethylenedioxy-8-hydroxytridecane
CAS No.:138890-28-5
Molecular Formula:C₃₆H₄₉NO₄
Molecular Weight:559.789
Hs Code.:

Synonyms:(6S,8R,9S)-6-(Dibenzylamino)-9-(benzyloxy)-2,2-ethylenedioxy-8-hydroxytridecane

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (6S,8R,9S)-6-(Dibenzylamino)-9-(benzyloxy)-2,2-ethylenedioxy-8-hydroxytridecane

Chemical Property:

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Technology Process of (6S,8R,9S)-6-(Dibenzylamino)-9-(benzyloxy)-2,2-ethylenedioxy-8-hydroxytridecane

There total 17 articles about (6S,8R,9S)-6-(Dibenzylamino)-9-(benzyloxy)-2,2-ethylenedioxy-8-hydroxytridecane 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: 87.0%

: 100-39-0
benzyl bromide

: 138890-27-4
(6S,8R,9S)-6-(Benzylamino)-9-(benzyloxy)-2,2-ethylenedioxy-8-hydroxytridecane

: 138890-28-5
(6S,8R,9S)-6-(Dibenzylamino)-9-(benzyloxy)-2,2-ethylenedioxy-8-hydroxytridecane

Guidance literature:: With sodium carbonate; In N,N-dimethyl-formamide; at 100 ℃; for 2h;
DOI:10.1016/S0040-4020(01)80881-4

Reference yield:

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

: 138890-28-5
(6S,8R,9S)-6-(Dibenzylamino)-9-(benzyloxy)-2,2-ethylenedioxy-8-hydroxytridecane

Guidance literature:: Multi-step reaction with 16 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: 1) sat. aq. Na₂CO₃, 2) 30percent aq. NH₃ / 1) CH₂Cl₂, room temp., 2 h, 2) ambient temp., 15 min

13: 89 percent / O₂ / PdCl₂, CuCl₂ / dimethylformamide; H₂O / 4 h / 50 °C

14: 89 percent / p-TsOH, molecular sieves / benzene / 14 h / Heating

15: 75 percent / saturated aq. KOH / ethanol / 15 h / 100 °C

16: 87 percent / Na₂CO₃ / dimethylformamide / 2 h / 100 °C

With hydrogenchloride; dmap; potassium hydroxide; ammonium hydroxide; lithium aluminium tetrahydride; molecular sieve; dilithium tetrachlorocuprate; oxygen; acetic anhydride; sodium carbonate; toluene-4-sulfonic acid; 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; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; butanone; benzene;
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

: 138890-28-5
(6S,8R,9S)-6-(Dibenzylamino)-9-(benzyloxy)-2,2-ethylenedioxy-8-hydroxytridecane

Guidance literature:: Multi-step reaction with 15 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: 1) sat. aq. Na₂CO₃, 2) 30percent aq. NH₃ / 1) CH₂Cl₂, room temp., 2 h, 2) ambient temp., 15 min

12: 89 percent / O₂ / PdCl₂, CuCl₂ / dimethylformamide; H₂O / 4 h / 50 °C

13: 89 percent / p-TsOH, molecular sieves / benzene / 14 h / Heating

14: 75 percent / saturated aq. KOH / ethanol / 15 h / 100 °C

15: 87 percent / Na₂CO₃ / dimethylformamide / 2 h / 100 °C

With hydrogenchloride; dmap; potassium hydroxide; ammonium hydroxide; lithium aluminium tetrahydride; molecular sieve; dilithium tetrachlorocuprate; oxygen; acetic anhydride; sodium carbonate; toluene-4-sulfonic acid; 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; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; butanone; benzene;
DOI:10.1016/S0040-4020(01)80881-4