Tetradehydropodophyllotoxin

Base Information

• Chemical Name: Tetradehydropodophyllotoxin
• CAS No.: 42123-27-3
• Molecular Formula: C₂₂H₁₈O₈
• Molecular Weight: 410.38
• Mol file: 42123-27-3.mol

Synonyms:dehydropodophyllotoxin

Chemical Property of Tetradehydropodophyllotoxin

Chemical Property:

• Melting Point: 286-288 °C (decomp)
• Boiling Point: 638.0±55.0 °C(Predicted)
• PKA: 7.63±0.20(Predicted)
• Density: 1.429±0.06 g/cm3(Predicted)

Purity/Quality:

≥98% ^*data from raw suppliers

Tetradehydropodophyllotoxin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Tetradehydropodophyllotoxin is a aryl-naphthalene lignans that was shown to exhibit anticancer activities.

Technology Process of Tetradehydropodophyllotoxin

There total 22 articles about Tetradehydropodophyllotoxin 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: 85.0%

podophyllotoxone (477-48-5,477-49-6,55515-07-6,60660-51-7,64550-42-1,64937-82-2,86594-36-7,130322-38-2) → dehydropodophyllotoxin (42123-27-3)

Guidance literature:

With C_. pseudotropicalis; In ethanol; water; at 37 ℃; for 336h; Product distribution; other reagents;

DOI:10.1016/S0960-894X(97)00101-7

Reference yield: 85.0%

(5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione (477-48-5) → dehydropodophyllotoxin (42123-27-3)

Guidance literature:

With C_. pseudotropicalis; In ethanol; water; at 37 ℃; Product distribution; other reagents;

DOI:10.1016/S0960-894X(97)00101-7

Reference yield: 80.0%

dimethyl 4-hydroxy-6,7-methylenedioxy-1-(3',4',5'-trimethoxyphenyl)naphthalene-2,3-dicarboxylate (42123-24-0) → dehydropodophyllotoxin (42123-27-3)

Guidance literature:

With sodium tetrahydroborate; In methanol; for 3h;

upstream raw materials:

(5aR,8aS,9R)-9-(3,4,5-trimethoxyphenyl)-5a,6,8a,9-tetrahydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxole-5,8-dione

podophyllotoxone

dimethyl 4-hydroxy-6,7-methylenedioxy-1-(3',4',5'-trimethoxyphenyl)naphthalene-2,3-dicarboxylate

tert-butyldimethylsilyldehydropodophyllotoxin

Downstream raw materials:

8-oxo-9-(3,4,5-trimethoxyphenyl)-6,8-dihydrofuro[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl trifluoromethanesulfonate

5-(3,4,5-Trimethoxy-phenyl)-8H-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-6-one

Refernces

• 1、 Sato, Yoshihiro,Tamura, Takayuki,Kinbara, Atsushi,Mori, Miwako. "Synthesis of biaryls via palladium-catalyzed [2+2+2] cocyclization of arynes and diynes: Application to the synthesis of arylnaphthalene lignans". . p. 647 - 661. Retrieved 2008/02/09.
• 2、 Mitra, Jayati,Mitra, Alok Kumar. "Carbon-13 NMR Chemical Shifts of some Podophyllum Lignans and Analogues". . p. 692 - 694. Retrieved 2007/10/03.