(3S,4R,5R)-4-allyl-3-(2-methyl)allyl-3-benzenesulfonyl-5-propyldihydrofuran-2-one

Base Information

Chemical Name:(3S,4R,5R)-4-allyl-3-(2-methyl)allyl-3-benzenesulfonyl-5-propyldihydrofuran-2-one
CAS No.:817617-07-5
Molecular Formula:C₂₀H₂₆O₄S
Molecular Weight:362.49
Hs Code.:

Synonyms:(3S,4R,5R)-4-allyl-3-(2-methyl)allyl-3-benzenesulfonyl-5-propyldihydrofuran-2-one

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Chemical Property of (3S,4R,5R)-4-allyl-3-(2-methyl)allyl-3-benzenesulfonyl-5-propyldihydrofuran-2-one

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Technology Process of (3S,4R,5R)-4-allyl-3-(2-methyl)allyl-3-benzenesulfonyl-5-propyldihydrofuran-2-one

There total 10 articles about (3S,4R,5R)-4-allyl-3-(2-methyl)allyl-3-benzenesulfonyl-5-propyldihydrofuran-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:

: 89321-71-1
(2S,3S)-3-propyl-2-oxiranemethanol

: 817617-07-5
(3S,4R,5R)-4-allyl-3-(2-methyl)allyl-3-benzenesulfonyl-5-propyldihydrofuran-2-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: 94 percent / Ti(OPr-i)4 / CH₂Cl₂ / 2 h / 20 °C

2.1: NaIO₄; tetrabutylammonium periodate / methanol; H₂O / 1 h / 20 °C

2.2: 73 percent / sodium hydride / benzene / 0.5 h

3.1: 95 percent / sodium hydride / dimethylformamide / 4 h

4.1: 92 percent / NaOH / tetrahydrofuran; H₂O / 1 h

5.1: 88 percent / BH₃*SMe₂ / tetrahydrofuran / -10 - 20 °C

6.1: 93 percent / KHSO₅ / methanol; H₂O / 5 h

7.1: dimethylformamide / 0.25 h / 0 °C

7.2: 60 percent / dimethylformamide / 4 h / 20 °C

8.1: methyl suldoxide; triethylamine; SO₃*pyridine / CH₂Cl₂ / 4 h / 20 °C

9.1: 237 mg / potassium hexamethyldisilazane / toluene; tetrahydrofuran / 1 h / -40 °C

With titanium(IV) isopropylate; sodium hydroxide; sodium periodate; potassium peroxomonosulfate; potassium hexamethyldisilazane; pyridine-SO₃ complex; dimethylsulfide borane complex; sodium hydride; tetrabutylammonium periodite; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.jorganchem.2006.08.021

Reference yield:

: [(2R,3R,4S)-4-Benzenesulfonyl-4-(2-methyl-allyl)-5-oxo-2-propyl-tetrahydro-furan-3-yl]-acetaldehyde

: 1779-49-3
Methyltriphenylphosphonium bromide

: 817617-07-5
(3S,4R,5R)-4-allyl-3-(2-methyl)allyl-3-benzenesulfonyl-5-propyldihydrofuran-2-one

Guidance literature:: With potassium hexamethylsilazane; In tetrahydrofuran; toluene; at -40 ℃; for 1h;
DOI:10.1021/ol0478739

Reference yield:

: 750544-42-4
(2R,3R,4S)-[5-oxo-4-(phenylthio)-2-propyl-tetrahydrofuran-3-yl]acetic acid

: 817617-07-5
(3S,4R,5R)-4-allyl-3-(2-methyl)allyl-3-benzenesulfonyl-5-propyldihydrofuran-2-one

Guidance literature:: Multi-step reaction with 5 steps

1.1: 88 percent / BH₃*SMe₂ / tetrahydrofuran / -10 - 20 °C

2.1: 93 percent / KHSO₅ / methanol; H₂O / 5 h

3.1: dimethylformamide / 0.25 h / 0 °C

3.2: 60 percent / dimethylformamide / 4 h / 20 °C

4.1: methyl suldoxide; triethylamine; SO₃*pyridine / CH₂Cl₂ / 4 h / 20 °C

5.1: 237 mg / potassium hexamethyldisilazane / toluene; tetrahydrofuran / 1 h / -40 °C

With potassium peroxomonosulfate; potassium hexamethyldisilazane; pyridine-SO₃ complex; dimethylsulfide borane complex; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.jorganchem.2006.08.021