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

Base Information

• Chemical Name: (1S,4S,5S,8S)-4,8-bis(3,4,5-trimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-2,6-dione
• CAS No.: 886989-85-1
• Molecular Formula: C₂₄H₂₆O₁₀
• Molecular Weight: 474.464
• Mol file: 886989-85-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about (1S,4S,5S,8S)-4,8-bis(3,4,5-trimethoxyphenyl)-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: 52.0%

(S)-1-[(E)-3-(3,4,5-trimethoxyphenyl)propenoyl]pyrrolidine-2-carboxylic acid (886989-84-0) → (1S,4S,5S,8S)-4,8-bis(3,4,5-trimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-2,6-dione (886989-85-1)

Guidance literature:

With tetrabutylammonium tetrafluoroborate; trifluoroacetic acid; In dichloromethane; at -40 ℃; for 3.76667h; enantioselective reaction; Electrochemical reaction;

DOI:10.1016/j.tet.2016.10.058

Reference yield: 25.0%

(E)-1-(pyrrolidine-1-yl)-3-(3,4,5-trimethoxyphenyl)-prop-2-en-1-one (1703-35-1,886989-88-4) → (1S,4S,5S,8S)-4,8-bis(3,4,5-trimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-2,6-dione (886989-85-1)

Guidance literature:

With Celite; lead dioxide; trifluoroacetic acid; In dichloromethane; water; at -78 ℃;

DOI:10.1055/s-2006-926271

Reference yield:

1,4-bis[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]butan-1,4-dione (879326-56-4) + 3,4,5-trimethoxy-benzaldehyde (86-81-7) → (1S,4S,5S,8S)-4,8-bis(3,4,5-trimethoxyphenyl)-3,7-dioxabicyclo[3.3.0]octane-2,6-dione (886989-85-1)

Guidance literature:

1,4-bis[(4S)-4-benzyl-2-oxo-1,3-oxazolidin-3-yl]butan-1,4-dione; 3,4,5-trimethoxy-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

upstream raw materials:

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

3,4,5-trimethoxy-benzaldehyde

(S)-1-[(E)-3-(3,4,5-trimethoxyphenyl)propenoyl]pyrrolidine-2-carboxylic acid

(E)-1-(pyrrolidine-1-yl)-3-(3,4,5-trimethoxyphenyl)-prop-2-en-1-one

Downstream raw materials:

(+)-yangambin

(1S,2R,3R,4S)-2,3-bis(hydroxymethyl)-1,4-bis(3,4,5-trimethoxyphenyl)butane-1,4-diol