(3S,4R,5R)-3-Benzenesulfonyl-4-(2-hex-5-enyloxy-ethyl)-5-propyl-dihydro-furan-2-one

Base Information

Chemical Name:(3S,4R,5R)-3-Benzenesulfonyl-4-(2-hex-5-enyloxy-ethyl)-5-propyl-dihydro-furan-2-one
CAS No.:817616-91-4
Molecular Formula:C₂₁H₃₀O₅S
Molecular Weight:394.532
Hs Code.:

Synonyms:(3S,4R,5R)-3-Benzenesulfonyl-4-(2-hex-5-enyloxy-ethyl)-5-propyl-dihydro-furan-2-one

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Chemical Property of (3S,4R,5R)-3-Benzenesulfonyl-4-(2-hex-5-enyloxy-ethyl)-5-propyl-dihydro-furan-2-one

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Technology Process of (3S,4R,5R)-3-Benzenesulfonyl-4-(2-hex-5-enyloxy-ethyl)-5-propyl-dihydro-furan-2-one

There total 9 articles about (3S,4R,5R)-3-Benzenesulfonyl-4-(2-hex-5-enyloxy-ethyl)-5-propyl-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: 58.0%

: 817616-83-4
(3S,4R,5R)-3-benzenesulfonyl-4-(2-hydroxyethyl)-5-propyldihydrofuran-2(3H)-one

: 2695-47-8
6-Bromo-1-hexene

: 817616-91-4
(3S,4R,5R)-3-Benzenesulfonyl-4-(2-hex-5-enyloxy-ethyl)-5-propyl-dihydro-furan-2-one

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 12h;
DOI:10.1021/ol0478739

Reference yield:

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

: 817616-91-4
(3S,4R,5R)-3-Benzenesulfonyl-4-(2-hex-5-enyloxy-ethyl)-5-propyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 8 steps

1: 94 percent / Ti(O-i-Pr)4 / CH₂Cl₂ / 0 - 20 °C

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

3: 7.92 g / NaH / benzene / 0.5 h / 0 °C

4: 95 percent / NaH / dimethylformamide / 4 h / -50 °C

5: 92 percent / NaOH; H₂O / tetrahydrofuran / 1 h

6: 88 percent / BH₃*SMe₂ / tetrahydrofuran / -10 - 20 °C

7: 93 percent / aq. KHSO₅ / methanol / 5 h / 0 °C

8: 58 percent / NaH / dimethylformamide / 12 h / 0 - 20 °C

With titanium(IV) isopropylate; sodium hydroxide; sodium periodate; potassium peroxomonosulfate; dimethylsulfide borane complex; water; sodium hydride; tetrabutylammonium periodite; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene;
DOI:10.1021/ol0478739

Reference yield:

: 817616-81-2
(3S,4R,5R)-4-(2-hydroxyethyl)-3-phenylthio-5-propyldihydrofuran-2(3H)-one

: 817616-91-4
(3S,4R,5R)-3-Benzenesulfonyl-4-(2-hex-5-enyloxy-ethyl)-5-propyl-dihydro-furan-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: 93 percent / aq. KHSO₅ / methanol / 5 h / 0 °C

2: 58 percent / NaH / dimethylformamide / 12 h / 0 - 20 °C

With potassium peroxomonosulfate; sodium hydride; In methanol; N,N-dimethyl-formamide;
DOI:10.1021/ol0478739