(2R,3S,4S)-5-benzyloxy-1-[(2S)-(1,4-dioxaspiro[4.5]dec-2-yl)]-3-hydroxy-2,4-dimethylpentan-1-one

Base Information

Chemical Name:(2R,3S,4S)-5-benzyloxy-1-[(2S)-(1,4-dioxaspiro[4.5]dec-2-yl)]-3-hydroxy-2,4-dimethylpentan-1-one
CAS No.:868134-33-2
Molecular Formula:C₂₂H₃₂O₅
Molecular Weight:376.493
Hs Code.:

Synonyms:(2R,3S,4S)-5-benzyloxy-1-[(2S)-(1,4-dioxaspiro[4.5]dec-2-yl)]-3-hydroxy-2,4-dimethylpentan-1-one

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Chemical Property of (2R,3S,4S)-5-benzyloxy-1-[(2S)-(1,4-dioxaspiro[4.5]dec-2-yl)]-3-hydroxy-2,4-dimethylpentan-1-one

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Technology Process of (2R,3S,4S)-5-benzyloxy-1-[(2S)-(1,4-dioxaspiro[4.5]dec-2-yl)]-3-hydroxy-2,4-dimethylpentan-1-one

There total 1 articles about (2R,3S,4S)-5-benzyloxy-1-[(2S)-(1,4-dioxaspiro[4.5]dec-2-yl)]-3-hydroxy-2,4-dimethylpentan-1-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: 80.0%

: 79027-28-4
(2S)-3-(benzyloxy)-2-methylpropanal

: 308795-19-9
(2S)-1,2-O-cyclohexylidene-1,2-dihydroxypentan-3-one

: 868134-33-2
(2R,3S,4S)-5-benzyloxy-1-[(2S)-(1,4-dioxaspiro[4.5]dec-2-yl)]-3-hydroxy-2,4-dimethylpentan-1-one

Guidance literature:: (2S)-1,2-O-cyclohexylidene-1,2-dihydroxypentan-3-one; With dicyclohexylboron chloride; triethylamine; In diethyl ether; at 0 ℃; for 0.5h;

(2S)-3-(benzyloxy)-2-methylpropanal; In diethyl ether; at 0 ℃; for 5h;
DOI:10.1021/jo051307p

Reference yield:

: 868134-33-2
(2R,3S,4S)-5-benzyloxy-1-[(2S)-(1,4-dioxaspiro[4.5]dec-2-yl)]-3-hydroxy-2,4-dimethylpentan-1-one

: 868134-34-3
(1S,2R,3S,4S)-5-benzyloxy-1-[(2S)-(1,4-dioxaspiro[4.5]dec-2-yl)]-2,4-dimethylpentane-1,3-diol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; diethyl ether; at -78 ℃; for 2h;
DOI:10.1021/jo051307p

Reference yield:

: 868134-33-2
(2R,3S,4S)-5-benzyloxy-1-[(2S)-(1,4-dioxaspiro[4.5]dec-2-yl)]-3-hydroxy-2,4-dimethylpentan-1-one

: (2S,3R,4S,5S,6S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-6-((S)-2-hydroxy-1-methyl-ethyl)-3-methoxy-5-methyl-tetrahydro-pyran-2,4-diol

Guidance literature:: Multi-step reaction with 12 steps

1.1: 2.8 g / LiAlH₄ / diethyl ether; tetrahydrofuran / 2 h / -78 °C

2.1: 93 percent / KH; tetra-n-butylammonium iodide / tetrahydrofuran / 2 h / 20 °C

3.1: 87 percent / ZnBr₂ / CH₂Cl₂ / 3 h / 20 °C

4.1: 95 percent / imidazole / CH₂Cl₂ / 20 °C

5.1: 89 percent / 1,8-bis(N,N-dimethylamino)naphthalene / CH₂Cl₂ / 3 h / 20 °C

6.1: 85 percent / tetra-n-butylammonium fluoride trihydrate / tetrahydrofuran / 20 °C

7.1: DMSO; (COCl)2; Et₃N / CH₂Cl₂ / -78 - 0 °C

8.1: Bu₂BOTf; Et₃N / CH₂Cl₂ / -78 - 0 °C

8.2: 1.11 g / CH₂Cl₂ / -78 - -20 °C

9.1: 89 percent / LiBH₄; EtOH / tetrahydrofuran; diethyl ether / 2 h / -10 °C

10.1: 89 percent / imidazole / CH₂Cl₂ / 20 °C

11.1: 85 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 0.75 h / 20 °C

12.1: H₂ / Pd/C / ethyl acetate / 16 h / 26600 Torr

With 1H-imidazole; lithium aluminium tetrahydride; lithium borohydride; oxalyl dichloride; ethanol; di-n-butylboryl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; hydrogen; tetra-(n-butyl)ammonium iodide; potassium hydride; N,N,N',N'-tetramethyl-1,8-diaminonaphthalene; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; triethylamine; zinc dibromide; palladium on activated charcoal; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; 7.1: Swern oxidation / 11.1: Dess-Martin oxidation;
DOI:10.1021/jo051307p