(-)-isodesoxypodophyllotoxine

Base Information

• Chemical Name: (-)-isodesoxypodophyllotoxine
• CAS No.: 100348-38-7
• Molecular Formula: C₂₂H₂₂O₇
• Molecular Weight: 398.412
• Mol file: 100348-38-7.mol

Synonyms:

Chemical Property of (-)-isodesoxypodophyllotoxine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-isodesoxypodophyllotoxine

There total 173 articles about (-)-isodesoxypodophyllotoxine 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:

diiodomethane

6,7-demethylenedeoxypodophyllotoxin

(+)-γ-apopodophyllic acid

(5S,6S,7R)-7-Hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid

Downstream raw materials:

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

Methanesulfonic acid (5R,6R,7R)-7-methoxymethoxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-6-ylmethyl ester

(5R,6R,7R)-7-Methoxymethoxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid ethyl ester

[(5R,6R,7R)-7-Methoxymethoxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxol-6-yl]-methanol

Refernces

• 1、 Hartwell et al.. "-". . p. 2138. Retrieved 1953.
• 2、 Li, Jian,Zhang, Xiao,Renata, Hans. "Asymmetric Chemoenzymatic Synthesis of (?)-Podophyllotoxin and Related Aryltetralin Lignans". supporting information. p. 11657 - 11660. Retrieved 2019/08/02.
• 3、 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.