(3S)-3-[(1S,2S)-2-dibenzylamino-1-hydroxy-4-methyl-pentyl]-dihydro-furan-2-one

Base Information

Chemical Name:(3S)-3-[(1S,2S)-2-dibenzylamino-1-hydroxy-4-methyl-pentyl]-dihydro-furan-2-one
CAS No.:864366-58-5
Molecular Formula:C₂₄H₃₁NO₃
Molecular Weight:381.515
Hs Code.:

Synonyms:(3S)-3-[(1S,2S)-2-dibenzylamino-1-hydroxy-4-methyl-pentyl]-dihydro-furan-2-one

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Chemical Property of (3S)-3-[(1S,2S)-2-dibenzylamino-1-hydroxy-4-methyl-pentyl]-dihydro-furan-2-one

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Technology Process of (3S)-3-[(1S,2S)-2-dibenzylamino-1-hydroxy-4-methyl-pentyl]-dihydro-furan-2-one

There total 1 articles about (3S)-3-[(1S,2S)-2-dibenzylamino-1-hydroxy-4-methyl-pentyl]-dihydro-furan-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: 50.0%

: 51425-66-2
(4,5-dihydro-2-furanyloxy)(trimethyl)silane

: 111060-65-2
(S)-2-(dibenzylamino)-4-methylpentanal

: 864366-57-4
(3R)-3-[(1R,2S)-2-dibenzylamino-1-hydroxy-4-methyl-pentyl]-dihydro-furan-2-one

: 864366-58-5
(3S)-3-[(1S,2S)-2-dibenzylamino-1-hydroxy-4-methyl-pentyl]-dihydro-furan-2-one

Guidance literature:: (S)-2-(dibenzylamino)-4-methylpentanal; With copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at 20 ℃; for 0.25h;

(4,5-dihydro-2-furanyloxy)(trimethyl)silane; In dichloromethane; at 20 ℃; for 5h;
DOI:10.1021/jo050749y

Reference yield: 95.0%

: 864366-58-5
(3S)-3-[(1S,2S)-2-dibenzylamino-1-hydroxy-4-methyl-pentyl]-dihydro-furan-2-one

: 69739-34-0
t-butyldimethylsiyl triflate

: 864366-73-4
(3S)-3-[(1S,2S)-1-(tert-butyl-dimethyl-silanyloxy)-2-dibenzylamino-4-methyl-pentyl]-dihydro-furan-2-one

Guidance literature:: With 2,6-dimethylpyridine;
DOI:10.1021/jo050749y

Reference yield:

: 864366-58-5
(3S)-3-[(1S,2S)-2-dibenzylamino-1-hydroxy-4-methyl-pentyl]-dihydro-furan-2-one

: 864366-90-5
[(S)-1-{(S)-1-[(S)-((2R,3S)-2-Butylcarbamoyl-tetrahydro-furan-3-yl)-hydroxy-methyl]-3-methyl-butylcarbamoyl}-2-(trityl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 14 steps

1.1: 95 percent / 2,6-lutidine

2.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C

2.2: tetrahydrofuran; hexane / 0.67 h / -78 °C

2.3: 58 percent / NaBH₄ / methanol / 20 °C

3.1: 87 percent / PPh₃; DEAD / tetrahydrofuran / 3 h / 20 °C

4.1: 84 percent / HgO; BF₃*Et₂O / tetrahydrofuran; H₂O / 24 h / 20 °C

5.1: NaClO₂; NaH₂PO₄*2H₂O; 2-methyl-2-butene / acetonitrile; 2-methyl-propan-2-ol; H₂O / 0.5 h / 0 °C

6.1: 18 mg / CH₂Cl₂; diethyl ether / 0 °C

7.1: NaOMe / methanol / 6 h / 70 °C

8.1: 82 mg / NaOH / methanol; H₂O / 12 h / 20 °C

9.1: 80 percent / PyBOP; i-Pr₂NEt / CH₂Cl₂ / 14 h / 0 - 20 °C

10.1: HCOOH / Pd / methanol / 20 °C

11.1: NaHCO₃ / methanol / 14 h / 20 °C

12.1: 14 mg / TBAF / tetrahydrofuran / 0.5 h / 0 °C

13.1: HCl / dioxane / 1 h / 20 °C

14.1: 27 mg / PyBOP; i-Pr₂NEt / CH₂Cl₂ / 2 h / 0 - 20 °C

With 2,6-dimethylpyridine; hydrogenchloride; sodium hydroxide; sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; formic acid; 2-methyl-but-2-ene; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium methylate; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; mercury(II) oxide; diethylazodicarboxylate; palladium; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; hexane; dichloromethane; water; acetonitrile; tert-butyl alcohol; 3.1: Mitsunobu reaction;
DOI:10.1021/jo050749y