(+)-(4R,5R)-4-Butyl-5-<(1S,2R)-4-(benzyloxy)-2-hydroxy-1-methoxybutyl>dihydrofuran-2(3H)-one

Base Information

Chemical Name:(+)-(4R,5R)-4-Butyl-5-<(1S,2R)-4-(benzyloxy)-2-hydroxy-1-methoxybutyl>dihydrofuran-2(3H)-one
CAS No.:78249-18-0
Molecular Formula:C₂₀H₃₀O₅
Molecular Weight:350.455
Hs Code.:

Synonyms:(+)-(4R,5R)-4-Butyl-5-<(1S,2R)-4-(benzyloxy)-2-hydroxy-1-methoxybutyl>dihydrofuran-2(3H)-one

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Chemical Property of (+)-(4R,5R)-4-Butyl-5-<(1S,2R)-4-(benzyloxy)-2-hydroxy-1-methoxybutyl>dihydrofuran-2(3H)-one

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Technology Process of (+)-(4R,5R)-4-Butyl-5-<(1S,2R)-4-(benzyloxy)-2-hydroxy-1-methoxybutyl>dihydrofuran-2(3H)-one

There total 9 articles about (+)-(4R,5R)-4-Butyl-5-<(1S,2R)-4-(benzyloxy)-2-hydroxy-1-methoxybutyl>dihydrofuran-2(3H)-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: 59.0%

: 78249-24-8
(4S,5S)-2-<(2S,3S,4R,5R)-7-(Benzyloxy)-3,5-(benzylidenedioxy)-4-methoxy-2-butylheptyl>-4-(methoxymethyl)-5-phenyl-2-oxazoline

: 78306-81-7
(4R,5S)-5-((1S,2R)-4-Benzyloxy-2-hydroxy-1-methoxy-butyl)-4-butyl-dihydro-furan-2-one

: 78249-18-0
(+)-(4R,5R)-4-Butyl-5-<(1S,2R)-4-(benzyloxy)-2-hydroxy-1-methoxybutyl>dihydrofuran-2(3H)-one

: 100-52-7
benzaldehyde

Guidance literature:: With sulfuric acid; In methanol; at 25 ℃; for 24h; Yields of byproduct given;
DOI:10.1021/jo00332a023

Reference yield:

: 19877-09-9
5,6-dideoxy-1,2-O-isopropylidene-3-O-methyl-alpha-D-xylo-hex-5-enofuranose

: 78249-18-0
(+)-(4R,5R)-4-Butyl-5-<(1S,2R)-4-(benzyloxy)-2-hydroxy-1-methoxybutyl>dihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) 2-methyl-2-butene, (CH₃)2S*BH₃, 2.) 30percent H₂O₂, 3N NaOH / 1.) THF, 0-25 deg C, 18.5h, 2.) 0-25 deg C, 2.0h

2: 93 percent / 1.) NaH / tetrahydrofuran / 1.) reflux, 1h, 2.) 25 deg C, 17.5h

3: 4percent H₂SO₄ aq / dioxane / 2 h / Heating

4: NaBH₄ / ethanol / 72 h / Ambient temperature

5: H₂SO₄ aq / CH₂Cl₂ / 46 h / molecular sieves

6: 90 percent / CrO₃, (CH₃CO)2O, C₅H₅N / CH₂Cl₂ / 0.33 h

7: NaH / 1.) 1,2-dimethoxyethane, room temp., 70 min, 2.) dimethoxyethane, 0 deg C, 4h

8: 78 percent / tetrahydrofuran; hexane / 2 h / -78 °C

9: 59 percent / 10percent H₂SO₄ aq / methanol / 24 h / 25 °C

With pyridine; chromium(VI) oxide; sodium hydroxide; sodium tetrahydroborate; 2-methyl-but-2-ene; dimethylsulfide borane complex; sulfuric acid; dihydrogen peroxide; acetic anhydride; sodium hydride; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane;
DOI:10.1021/jo00332a023

Reference yield:

: 62853-46-7
5-deoxy-3-O-methyl-1,2-O-(methylethylidene)-α-D-xylo-hexo-furanose

: 78249-18-0
(+)-(4R,5R)-4-Butyl-5-<(1S,2R)-4-(benzyloxy)-2-hydroxy-1-methoxybutyl>dihydrofuran-2(3H)-one

Guidance literature:: Multi-step reaction with 8 steps

1: 93 percent / 1.) NaH / tetrahydrofuran / 1.) reflux, 1h, 2.) 25 deg C, 17.5h

2: 4percent H₂SO₄ aq / dioxane / 2 h / Heating

3: NaBH₄ / ethanol / 72 h / Ambient temperature

4: H₂SO₄ aq / CH₂Cl₂ / 46 h / molecular sieves

5: 90 percent / CrO₃, (CH₃CO)2O, C₅H₅N / CH₂Cl₂ / 0.33 h

6: NaH / 1.) 1,2-dimethoxyethane, room temp., 70 min, 2.) dimethoxyethane, 0 deg C, 4h

7: 78 percent / tetrahydrofuran; hexane / 2 h / -78 °C

8: 59 percent / 10percent H₂SO₄ aq / methanol / 24 h / 25 °C

With pyridine; chromium(VI) oxide; sodium tetrahydroborate; sulfuric acid; acetic anhydride; sodium hydride; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; hexane; dichloromethane;
DOI:10.1021/jo00332a023