(1S,4S,5S,8S)-4,8-bis(3,4-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-2,6-dione

Base Information

• Chemical Name: (1S,4S,5S,8S)-4,8-bis(3,4-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-2,6-dione
• CAS No.: 62653-83-2
• Molecular Formula: C₂₂H₂₂O₈
• Molecular Weight: 414.412

Synonyms:(1S,4S,5S,8S)-4,8-bis(3,4-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-2,6-dione

Chemical Property of (1S,4S,5S,8S)-4,8-bis(3,4-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-2,6-dione

Chemical Property:

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Technology Process of (1S,4S,5S,8S)-4,8-bis(3,4-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-2,6-dione

There total 9 articles about (1S,4S,5S,8S)-4,8-bis(3,4-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-2,6-dione 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: 84.0%

1,4-Bis-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ6-thia-4-aza-tricyclo[5.2.1.01,5]dec-4-yl)-butane-1,4-dione + 3,4-dimethoxy-benzaldehyde (120-14-9) → (1S,4S,5S,8S)-4,8-bis(3,4-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-2,6-dione (62653-83-2)

Guidance literature:

1,4-Bis-((1S,5R,7R)-10,10-dimethyl-3,3-dioxo-3λ⁶-thia-4-aza-tricyclo[5.2.1.0^1,5]dec-4-yl)-butane-1,4-dione; 3,4-dimethoxy-benzaldehyde; With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at -78 - 0 ℃;

With potassium dihydrogenphosphate; dihydrogen peroxide; In methanol; at 25 ℃; for 8h;

DOI:10.1016/j.tetlet.2006.06.127

Reference yield: 65.0%

(2S,3R)-2-[(S)-(3,4-Dimethoxy-phenyl)-hydroxy-methyl]-3-[(R)-(3,4-dimethoxy-phenyl)-hydroxy-methyl]-N1,N1,N4,N4-tetraethyl-succinamide (84838-27-7,85026-05-7) → (1S,4S,5S,8S)-4,8-bis(3,4-dimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-2,6-dione (62653-83-2) + (2R,3R)-2-(3,4-Dimethoxy-phenyl)-4-[1-(3,4-dimethoxy-phenyl)-meth-(Z)-ylidene]-5-oxo-tetrahydro-furan-3-carboxylic acid diethylamide (84838-28-8)

Guidance literature:

With acetic acid; for 18h; Heating;

DOI:10.1016/S0040-4039(00)88673-6

Reference yield: 57.0%

2,5-bis<(trimethylsilyl)oxy>furan (77220-06-5) + 3,4-dimethoxy-benzaldehyde (120-14-9) → (3S,3aS,6R,6aS)-3,6-Bis-(3,4-dimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1,4-dione (60031-92-7,62653-82-1,62653-83-2,69854-19-9,81968-22-1,114182-01-3) + 2,6-bis-(3,4-dimethoxyphenyl)-3,7-dioxabicyclo<3.3.0>octane-4,8-dione (69854-19-9)

Guidance literature:

With titanium tetrachloride; In dichloromethane; at -78 ℃; for 3h;

DOI:10.1016/S0040-4039(00)78706-5

upstream raw materials:

(2S,3R)-2-[(S)-(3,4-Dimethoxy-phenyl)-hydroxy-methyl]-3-[(R)-(3,4-dimethoxy-phenyl)-hydroxy-methyl]-N¹,N¹,N⁴,N⁴-tetraethyl-succinamide

1,4-bis[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]butan-1,4-dione

3,4-dimethoxy-benzaldehyde

3,4-dimethoxy-trans-cinnamic acid

Downstream raw materials:

(3S,3aS,6S,6aS)-3,6-Bis-(3,4-dimethoxy-phenyl)-tetrahydro-furo[3,4-c]furan-1,4-diol

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