(5R)-5-<(2S,3R)-2-benzyloxy-4-tert-butyldimethylsilyloxy-3-(phenoxythiocarbonyloxy)butyl>-2(5H)-furanone

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Chemical Name:(5R)-5-<(2S,3R)-2-benzyloxy-4-tert-butyldimethylsilyloxy-3-(phenoxythiocarbonyloxy)butyl>-2(5H)-furanone
CAS No.:160998-99-2
Molecular Formula:C₂₈H₃₆O₆SSi
Molecular Weight:528.742
Hs Code.:

Synonyms:(5R)-5-<(2S,3R)-2-benzyloxy-4-tert-butyldimethylsilyloxy-3-(phenoxythiocarbonyloxy)butyl>-2(5H)-furanone

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Chemical Property of (5R)-5-<(2S,3R)-2-benzyloxy-4-tert-butyldimethylsilyloxy-3-(phenoxythiocarbonyloxy)butyl>-2(5H)-furanone

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Technology Process of (5R)-5-<(2S,3R)-2-benzyloxy-4-tert-butyldimethylsilyloxy-3-(phenoxythiocarbonyloxy)butyl>-2(5H)-furanone

There total 6 articles about (5R)-5-<(2S,3R)-2-benzyloxy-4-tert-butyldimethylsilyloxy-3-(phenoxythiocarbonyloxy)butyl>-2(5H)-furanone 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: 97.0%

: (R)-5-[(2S,3R)-2-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-butyl]-5H-furan-2-one

: 1005-56-7
phenylcarbonochloridothioate

: 160998-99-2
(5R)-5-<(2S,3R)-2-benzyloxy-4-tert-butyldimethylsilyloxy-3-(phenoxythiocarbonyloxy)butyl>-2(5H)-furanone

Guidance literature:: With pyridine; dmap; In dichloromethane; for 3h; Heating;

Reference yield:

: 103795-36-4
(3S,4R)-3-O-benzyl-4,5-O-isopropylidene-3,4,5-trihydroxypentanal

: 160998-99-2
(5R)-5-<(2S,3R)-2-benzyloxy-4-tert-butyldimethylsilyloxy-3-(phenoxythiocarbonyloxy)butyl>-2(5H)-furanone

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) 1.6M BuLi / 1.) THF, Et₂O, pentane, hexane, -78 deg C, 15 min, 2.) THF, Et₂O, pentane, hexane, -78 deg C; quenching with Me₃SiCl

2: 1.) H₂, quinoline, 2.) TsOH / 1.) 5percent Pd/BaSO₄ / 1.) methanol, 22 deg C, 1 bar, 2.) methanol, pH 2.5, 22 deg C, 15 h

3: 97 percent / imidazole / dimethylformamide / 0.5 h / 22 °C

4: 97 percent / DMAP, pyridine / CH₂Cl₂ / 3 h / Heating

With pyridine; 1H-imidazole; quinoline; dmap; n-butyllithium; hydrogen; toluene-4-sulfonic acid; Pd-BaSO₄; In dichloromethane; N,N-dimethyl-formamide;

Reference yield:

: 87604-53-3
(R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane

: 160998-99-2
(5R)-5-<(2S,3R)-2-benzyloxy-4-tert-butyldimethylsilyloxy-3-(phenoxythiocarbonyloxy)butyl>-2(5H)-furanone

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) O₃, 2.) PPh₃ / 1.) methanol, -78 deg C, 2.) methanol, 12 h

2: 1.) 1.6M BuLi / 1.) THF, Et₂O, pentane, hexane, -78 deg C, 15 min, 2.) THF, Et₂O, pentane, hexane, -78 deg C; quenching with Me₃SiCl

3: 1.) H₂, quinoline, 2.) TsOH / 1.) 5percent Pd/BaSO₄ / 1.) methanol, 22 deg C, 1 bar, 2.) methanol, pH 2.5, 22 deg C, 15 h

4: 97 percent / imidazole / dimethylformamide / 0.5 h / 22 °C

5: 97 percent / DMAP, pyridine / CH₂Cl₂ / 3 h / Heating

With pyridine; 1H-imidazole; quinoline; dmap; n-butyllithium; hydrogen; toluene-4-sulfonic acid; ozone; triphenylphosphine; Pd-BaSO₄; In dichloromethane; N,N-dimethyl-formamide;