(3aS,3bR,5S,6aR,7aS)-5-Phenylsulfanyl-hexahydro-difuro[2,3-b;3',2'-d]furan-2-one

Base Information

Chemical Name:(3aS,3bR,5S,6aR,7aS)-5-Phenylsulfanyl-hexahydro-difuro[2,3-b;3',2'-d]furan-2-one
CAS No.:170238-22-9
Molecular Formula:C₁₄H₁₄O₄S
Molecular Weight:278.329
Hs Code.:

Synonyms:(3aS,3bR,5S,6aR,7aS)-5-Phenylsulfanyl-hexahydro-difuro[2,3-b;3',2'-d]furan-2-one

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Chemical Property of (3aS,3bR,5S,6aR,7aS)-5-Phenylsulfanyl-hexahydro-difuro[2,3-b;3',2'-d]furan-2-one

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Technology Process of (3aS,3bR,5S,6aR,7aS)-5-Phenylsulfanyl-hexahydro-difuro[2,3-b;3',2'-d]furan-2-one

There total 4 articles about (3aS,3bR,5S,6aR,7aS)-5-Phenylsulfanyl-hexahydro-difuro[2,3-b;3',2'-d]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: 52.0%

: 108-98-5
thiophenol

: 170238-21-8
(3aS,3bR,5R,6aS,7aS)-5-Methoxy-hexahydro-difuro[2,3-b;3',2'-d]furan-2-one

: 170238-22-9
(3aS,3bR,5S,6aR,7aS)-5-Phenylsulfanyl-hexahydro-difuro[2,3-b;3',2'-d]furan-2-one

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 1.75h;
DOI:10.1021/ja00142a051

Reference yield:

: (1S,3R,3aR,7aS)-1,3-Dimethoxy-6-methylene-octahydro-isobenzofuran-5-ol

: 170238-22-9
(3aS,3bR,5S,6aR,7aS)-5-Phenylsulfanyl-hexahydro-difuro[2,3-b;3',2'-d]furan-2-one

Guidance literature:: Multi-step reaction with 3 steps

1: 100 percent / NaIO₄, OsO₄, H₂O / 2-methyl-propan-2-ol / 1 h / 23 °C

2: 68 percent / MeSO₃H, 4A molecular sieves / CH₂Cl₂ / 1 h / -20 °C

3: 52 percent / BF₃*Et₂O / CH₂Cl₂ / 1.75 h / 0 °C

With sodium periodate; osmium(VIII) oxide; methanesulfonic acid; 4 A molecular sieve; boron trifluoride diethyl etherate; water; In dichloromethane; tert-butyl alcohol;
DOI:10.1021/ja00142a051

Reference yield:

: 170238-18-3
((1R,3S,3aS,7aR)-1,3-Dimethoxy-1,3,3a,4,7,7a-hexahydro-isobenzofuran-5-ylmethyl)-trimethyl-silane

: 170238-22-9
(3aS,3bR,5S,6aR,7aS)-5-Phenylsulfanyl-hexahydro-difuro[2,3-b;3',2'-d]furan-2-one

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) dimethyldioxirane, 2.) n-Bu₄NF / 1.) acetone, 0 deg C, 15 min, 2.) THF, 0 deg C, 40 min

2: 100 percent / NaIO₄, OsO₄, H₂O / 2-methyl-propan-2-ol / 1 h / 23 °C

3: 68 percent / MeSO₃H, 4A molecular sieves / CH₂Cl₂ / 1 h / -20 °C

4: 52 percent / BF₃*Et₂O / CH₂Cl₂ / 1.75 h / 0 °C

With sodium periodate; osmium(VIII) oxide; methanesulfonic acid; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; water; 3,3-dimethyldioxirane; In dichloromethane; tert-butyl alcohol;
DOI:10.1021/ja00142a051