Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, [5R-(5a,5aa,8ab)]- (9CI)

Base Information

• Chemical Name: Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, [5R-(5a,5aa,8ab)]- (9CI)
• CAS No.: 17187-81-4
• Molecular Formula: C22H22 O7
• Molecular Weight: 398.412

Synonyms:Isopodophyllotoxin,4-deoxy-, (+)- (8CI); (+)-Isodeoxypodophyllotoxin; Isodesoxypodophyllotoxin;NSC 332045

Chemical Property of Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, [5R-(5a,5aa,8ab)]- (9CI)

Chemical Property:

• Boiling Point: 564.5°Cat760mmHg
• Flash Point: 247°C
• Density: 1.304g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, [5R-(5a,5aa,8ab)]- (9CI)

There total 184 articles about Furo[3',4':6,7]naphtho[2,3-d]-1,3-dioxol-6(5aH)-one,5,8,8a,9-tetrahydro-5-(3,4,5-trimethoxyphenyl)-, [5R-(5a,5aa,8ab)]- (9CI) 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:

(S)-4-Benzo[1,3]dioxol-5-ylmethyl-3-[hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one

4-Benzo[1,3]dioxol-5-ylmethyl-3-[hydroxy-(3,4,5-trimethoxy-phenyl)-methyl]-dihydro-furan-2-one

acetic acid

α-apopicropodophyllotoxin

Downstream raw materials:

(-)-(1R,2S,3S)-1-(3,4,5-trimethoxyphenyl)-2-(methoxycarbonyl)-3-<<(tert-butyldimethylsilyl)oxy>methyl>-6,7-(methylenedioxy)-2,3-dihydro-4(1H)-naphtalenone

isodeoxypodophyllinic acid methyl ester

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

deoxypicropodophyllin

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