Deoxypicropodophyllotoxin

Base Information

• Chemical Name: Deoxypicropodophyllotoxin
• CAS No.: 24150-39-8
• Molecular Formula: C22H22 O7
• Molecular Weight: 398.412
• UNII: QCS5LR9WDT
• ChEMBL ID: CHEMBL519603
• Metabolomics Workbench ID: 141854
• Nikkaji Number: J513.312B
• Mol file: 24150-39-8.mol

Synonyms:deoxypicropodophyllin;deoxypodophyllotoxin;deoxypodophyllotoxin, (5alpha,5aalpha,8aalpha)-(+-)-isomer;deoxypodophyllotoxin, (5alpha,5aalpha,8abeta)-(+-)-isomer;deoxypodophyllotoxin, (5R-(5alpha,5aalpha,8aalpha))-isomer;deoxypodophyllotoxin, (5R-(5alpha,5aalpha,8abeta))-isomer;deoxypodophyllotoxin, (5R-(5alpha,5abeta,8aalpha))-isomer;deoxypodophyllotoxin, (5R-(5alpha,5abeta,8abeta))-isomer;isoanthricin;isodeoxypodophyllotoxin

Chemical Property of Deoxypicropodophyllotoxin

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 398.13655304
• Heavy Atom Count: 29
• Complexity: 598

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC(=CC(=C1OC)OC)C2C3C(CC4=CC5=C(C=C24)OCO5)COC3=O
• Isomeric SMILES: COC1=CC(=CC(=C1OC)OC)[C@H]2[C@H]3[C@@H](CC4=CC5=C(C=C24)OCO5)COC3=O

Technology Process of Deoxypicropodophyllotoxin

There total 187 articles about Deoxypicropodophyllotoxin 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: 95.0%

yatein (40456-50-6,17301-91-6,61091-56-3,72690-16-5,96745-44-7,119066-80-7,128049-89-8,139560-31-9) → deoxypodophyllotoxin (477-51-0,6258-33-9,17187-81-4,17301-90-5,19186-35-7,24150-39-8,31892-96-3,55568-81-5,64550-41-0,69222-20-4,75171-57-2,83023-41-0,100348-38-7)

Guidance literature:

With ferrous(II) sulfate heptahydrate; ATGGGCAGCACCGCGCCGCTGCGTTTCCCGGTTATCGATTTGAGCATGAAGAACCTGAAACCTGGAACCACATCATGGAACAGCGTACGCACTCAGGTGCGTGAAGCTTTGGAAGAATATGGTTGCTTTGAAGCCGTTATTGATGCGGTTTCCCCAGAGTTGCAAAAAGCTGTCTGCAACAAGGGGCACGAACTGTTAAATTTACCGCTGGAGACCAAGATGCTTAATGGTAATAAGCCGGAGTACGATGGATTTACATCAATCCCGAACCTTAACGAAGGTATGGGTGTTGGCCGCATCACTGACTTAGAGAAGGTCGAACGTTTCACTAATCTGATGTGGCCTGAGGGGAACAAGGATTTTTGCGAAACAGTTTACTCCTATGGTAAGCGCATGGCAGAGGTTGACCATATTCTGAAGATGATGGTATTCGAATCTTTTGGTATGGAGAAACATTTTGACTCCTTCTGCGAAAGTACAAATTACTTGCTGCATTTCATGCGCTATCAACAACCCGGCAAAGACGGTCGCTCTCCCGCATTGAGTTTACACAAAGATAAATCTATCCTTACGATCGTCAACCAAAACGATGTAAAAGGACTGGAGTTCGAAACAAAGGATGGCGAATGGATTTTGCCAACAGCCGATAACCACATCGTATTACTTGGAGATTGCTTCATGGCTTGGAGTAACGGTCGCCTGCACTCTCCACTGCACCGTGTGACATTAGTGGCAAATCAGGCACGTTTGAGTACCTCCTCATTTAGCTTCCCAAAAGATATTATTGAGACACCGGCGGAATTGGTGGACGAGGAACATCCGCTTTTATTCAATCCCTTCGAGATCACCGAGCTTTTAGCCTACTGTTTTACAAAAGAAGGAGCCAAGGCGGTTTGCGATTTAAAGCAGTATAAAGCGTACACTGGAGCATGA; α-ketoglutaric acid disodium salt; ascorbic acid; In dimethyl sulfoxide; at 23 ℃; for 20h;

DOI:10.1002/anie.201904102

Reference yield: 45.0%

3-methyl-butan-2-one (563-80-4) + 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) → 7α-[(2R)-2-hydroxy-3-methylbut-2-yl]epi-podophyllotoxin + 7α-[(2S)-2-hydroxy-3-methylbut-2-yl]epi-podophyllotoxin + deoxypodophyllotoxin (477-51-0,6258-33-9,17187-81-4,17301-90-5,19186-35-7,24150-39-8,31892-96-3,55568-81-5,64550-41-0,69222-20-4,75171-57-2,83023-41-0,100348-38-7) + podofilox (518-28-5)

Guidance literature:

With titanium tetrachloride; zinc; In tetrahydrofuran; at -20 - -10 ℃; for 4h; Inert atmosphere;

DOI:10.1021/jm2017573

Reference yield: 45.0%

acetone (67-64-1) + 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) → 7α-(2-hydroxyprop-2-yl)podophyllotoxin + 7β-(2-hydroxyprop-2-yl)podophyllotoxin + deoxypodophyllotoxin (477-51-0,6258-33-9,17187-81-4,17301-90-5,19186-35-7,24150-39-8,31892-96-3,55568-81-5,64550-41-0,69222-20-4,75171-57-2,83023-41-0,100348-38-7) + podofilox (518-28-5)

Guidance literature:

With titanium tetrachloride; zinc; In tetrahydrofuran; at -20 - -10 ℃; for 4h; optical yield given as %de; Inert atmosphere;

DOI:10.1021/jm2017573

upstream raw materials:

ethanol

sodium acetate

deoxypodophyllotoxin

1-methyl-4-nitrosobenzene

Downstream raw materials:

oxalic acid

Eudesmic acid

6,7-dihydroxy-9-(3,4,5-trimethoxy-phenyl)-3a,4,9,9a-tetrahydro-3H-naphtho[2,3-c]furan-1-one

2'-bromo-dehydrodesoxypodophyllotoxin

Refernces

• 1、 Li, Jian,Zhang, Xiao,Renata, Hans. "Asymmetric Chemoenzymatic Synthesis of (?)-Podophyllotoxin and Related Aryltetralin Lignans". supporting information. p. 11657 - 11660. Retrieved 2019/08/02.
• 2、 Xiao, Jian,Cong, Xiao-Wei,Yang, Gui-Zhen,Wang, Ya-Wen,Peng, Yu. "Divergent Asymmetric Syntheses of Podophyllotoxin and Related Family Members via Stereoselective Reductive Ni-Catalysis". supporting information. p. 1651 - 1654. Retrieved 2018/03/23.