Isoaltholactone

Base Information

• Chemical Name: Isoaltholactone
• CAS No.: 124868-11-7
• Molecular Formula: C₁₃H₁₂O₄
• Molecular Weight: 232.236
• Mol file: 124868-11-7.mol

Synonyms:2H-Furo[3,2-b]pyran,L-arabino-hept-2-enonic acid deriv.; (+)-Isoaltholactone; Isoaltholactone

Chemical Property of Isoaltholactone

Chemical Property:

• PSA: 55.76000
• LogP: 0.96900

Purity/Quality:

98%Min ^*data from raw suppliers

Isoaltholactone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Isoaltholactone

There total 48 articles about Isoaltholactone 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: 93.0%

(5S)-5-hydroxy-(6S)-6-((2S,3R)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one (302348-81-8) → (+)-7,8-di-epi-altholactone (124868-11-7,65408-91-5,114488-17-4,114488-19-6,120019-23-0,120019-27-4,124868-12-8)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 1.5h;

DOI:10.1021/ol000179i

Reference yield: 83.0%

(Z)-3-((3aR,4S,6S,6aS)-2,2-Dimethyl-6-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acrylic acid ethyl ester → (+)-7,8-di-epi-altholactone (124868-11-7,65408-91-5,114488-17-4,114488-19-6,120019-23-0,120019-27-4,124868-12-8)

Guidance literature:

(Z)-3-((3aR,4S,6S,6aS)-2,2-Dimethyl-6-phenyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acrylic acid ethyl ester; With toluene-4-sulfonic acid; In methanol; at 20 ℃;

In benzene; sonication;

DOI:10.1016/S0040-4039(03)01413-8

Reference yield: 83.0%

ethyl 3-[2,2-dimethyl-6-phenyl-(3aR,4S,6S,6aS)-perhydrofuro[3,4-d][1,3]dioxol-4-yl]-(Z)-2-propenoate → (+)-7,8-di-epi-altholactone (124868-11-7,65408-91-5,114488-17-4,114488-19-6,120019-23-0,120019-27-4,124868-12-8)

Guidance literature:

ethyl 3-[2,2-dimethyl-6-phenyl-(3aR,4S,6S,6aS)-perhydrofuro[3,4-d][1,3]dioxol-4-yl]-(Z)-2-propenoate; With toluene-4-sulfonic acid; In methanol; at 20 ℃;

In benzene; sonication;

DOI:10.1016/j.tetasy.2005.08.047

upstream raw materials:

(2S,3R,4S,5S)-2-<(Z)-2-(ethoxycarbonyl)-ethenyl>-3,4-bis(methoxymethoxy)-5-phenyltetrahydrofuran

(5S)-5-hydroxy-(6S)-6-((2S,3S)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one

(5S)-5-hydroxy-(6S)-6-((2S,3R)-3-phenyloxiranyl)-5,6-dihydro-pyran-2-one

(5S,6S)-5-hydroxy-6-[(E)-styryl]-5,6-dihydro-2H-pyran-2-one

Refernces

• 1、 Yadav, Jhillu Singh,Raju, Atcha Krishnam,Rao, Ponugoti Purushothama,Rajaiah, Gurram. "Highly stereoselective synthesis of antitumor agents: Both enantiomers of goniothales diol, altholactone, and isoaltholactone". . p. 3283 - 3290. Retrieved 2007/10/03.
• 2、 Peng, Xiaoshui,Li, Anpai,Lu, Jiangping,Wang, Qiaoling,Pan, Xinfu,Chan, Albert S.C. "Enantioselective total synthesis of (+)-isoaltholactone". . p. 6799 - 6804. Retrieved 2007/10/03.