(3R,3aR,5R,6S,7aS)-5,6-dihydroxy-7a-(phenylsulfonyl)-3-propyl-hexahydroisobenzofuran-1(3H)-one

Base Information

Chemical Name:(3R,3aR,5R,6S,7aS)-5,6-dihydroxy-7a-(phenylsulfonyl)-3-propyl-hexahydroisobenzofuran-1(3H)-one
CAS No.:817617-21-3
Molecular Formula:C₁₇H₂₂O₆S
Molecular Weight:354.424
Hs Code.:

Synonyms:(3R,3aR,5R,6S,7aS)-5,6-dihydroxy-7a-(phenylsulfonyl)-3-propyl-hexahydroisobenzofuran-1(3H)-one

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Chemical Property of (3R,3aR,5R,6S,7aS)-5,6-dihydroxy-7a-(phenylsulfonyl)-3-propyl-hexahydroisobenzofuran-1(3H)-one

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Technology Process of (3R,3aR,5R,6S,7aS)-5,6-dihydroxy-7a-(phenylsulfonyl)-3-propyl-hexahydroisobenzofuran-1(3H)-one

There total 13 articles about (3R,3aR,5R,6S,7aS)-5,6-dihydroxy-7a-(phenylsulfonyl)-3-propyl-hexahydroisobenzofuran-1(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:

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

: 817617-21-3
(3R,3aR,5R,6S,7aS)-5,6-dihydroxy-7a-(phenylsulfonyl)-3-propyl-hexahydroisobenzofuran-1(3H)-one

Guidance literature:: Multi-step reaction with 12 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: 75 percent / NaH / dimethylformamide / 4 h / 0 - 20 °C

9: SO₃*Py; Me₂SO; Et₃N / CH₂Cl₂ / 0 - 20 °C

10: 316.4 mg / KHDMS / toluene; tetrahydrofuran / 1 h / -40 °C

11: 85 percent / [1,3-dimesitylimidazolidin-2-yl]Cl₂(PCy₃)Ru=CHPh / CH₂Cl₂ / 3 h / 40 °C

12: 4-methylmorpholine N-oxide; OsO₄; H₂O / tetrahydrofuran; acetone / 2 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; titanium(IV) isopropylate; sodium hydroxide; sodium periodate; osmium(VIII) oxide; potassium peroxomonosulfate; pyridine-SO₃ complex; dimethylsulfide borane complex; water; potassium hexamethylsilazane; sodium hydride; tetrabutylammonium periodite; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene; 10: Wittig reaction;
DOI:10.1021/ol0478739

Reference yield:

: 817617-09-7
(3R,3aR,7aS)-7a-(phenylsulfonyl)-3-propyl-3a,4,7,7a-tetrahydroisobenzofuran-1(3H)-one

: 817617-21-3
(3R,3aR,5R,6S,7aS)-5,6-dihydroxy-7a-(phenylsulfonyl)-3-propyl-hexahydroisobenzofuran-1(3H)-one

: 817617-23-5
(3R,3aR,5S,6R,7aS)-5,6-dihydroxy-7a-(phenylsulfonyl)-3-propyl-hexahydroisobenzofuran-1(3H)-one

Guidance literature:: With osmium(VIII) oxide; water; 4-methylmorpholine N-oxide; In tetrahydrofuran; acetone; at 20 ℃; for 2h;
DOI:10.1021/ol0478739

Reference yield:

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

: 817617-21-3
(3R,3aR,5R,6S,7aS)-5,6-dihydroxy-7a-(phenylsulfonyl)-3-propyl-hexahydroisobenzofuran-1(3H)-one

Guidance literature:: Multi-step reaction with 6 steps

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

2: 75 percent / NaH / dimethylformamide / 4 h / 0 - 20 °C

3: SO₃*Py; Me₂SO; Et₃N / CH₂Cl₂ / 0 - 20 °C

4: 316.4 mg / KHDMS / toluene; tetrahydrofuran / 1 h / -40 °C

5: 85 percent / [1,3-dimesitylimidazolidin-2-yl]Cl₂(PCy₃)Ru=CHPh / CH₂Cl₂ / 3 h / 40 °C

6: 4-methylmorpholine N-oxide; OsO₄; H₂O / tetrahydrofuran; acetone / 2 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; osmium(VIII) oxide; potassium peroxomonosulfate; pyridine-SO₃ complex; water; potassium hexamethylsilazane; sodium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; 4: Wittig reaction;
DOI:10.1021/ol0478739