140147-76-8

Basic information

• Product Name: (5S,6S,7S)-7-Hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester
• CAS NO: 140147-76-8
• Molecular Weight: 430.455
• Mol File: 140147-76-8.mol

Chemical Properties

• CAS DataBase Reference: (5S,6S,7S)-7-Hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (5S,6S,7S)-7-Hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester(140147-76-8)
• EPA Substance Registry System: (5S,6S,7S)-7-Hydroxymethyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester(140147-76-8)

Safety Data

• Hazardous Substances Data: 140147-76-8(Hazardous Substances Data)

Upstream product

• 186581-53-3 diazomethane 
• 1254-07-5 deoxypicropodophyllic acid 
• 75101-87-0 C₂₄H₂₄O₁₀ 
• 75101-87-0 C₂₄H₂₄O₁₀ 
• 76886-74-3 C₂₄H₂₂O₁₀ 
• 75101-88-1 C₂₃H₂₄O₉ 
• 116097-18-8 6,7-methylenedioxy-1-(3',4',5'-trimethoxyphenyl)-2-benzopyran-3-one 
• 1256-91-3 (+/-)-methyl epipodophyllate 
• 477-51-0 deoxypodophyllotoxin 
• 67-56-1 methanol 
• 28071-35-4 (7S,8R,8'R)-9-O-acetyldihydrosesamin 
• 122763-50-2 methyl 3-(hydroxymethyl)-6,7-(methylenedioxy)-1-(1,2-cis)-(3',4',5'-trimethoxyphenyl)-1,2-dihydronaphthalene-2-carboxylate 

Downstream Products

• 171483-28-6 (5R,6S,7R)-7-Formyl-5-(3,4,5-trimethoxy-phenyl)-5,6,7,8-tetrahydro-naphtho[2,3-d][1,3]dioxole-6-carboxylic acid methyl ester 
• 477-51-0 rac-(7'β,8α,8'percentb)-3',4',5'-trimethoxy-4,5-methylenedioxy-2,7'-cyclolignan-9',9-olide 
• 477-51-0 (5S,5aS,8aR)-5-(3,4,5-trimethoxyphenyl)-5,8,8a,9-tetrahydrofuro[3′,4’:6,7]naphtho[2,3-d][1,3]-dioxol-6(5aH)-one 

Relevant articles and documents

LIGNANS FROM POLAR EXTRACTS OF JUNIPERUS THURIFERA

Three new natural lignans, methyl deoxypodophyllotoxinate, podophyllotoxinic acid and 7β-hydroxydihydrosesamin, 11 known lignans and two cinnamyl alcohols were isolated and identified from a chloroform extract of Juniperus thurifera leaves.Assignment of the (13)C NMR spectrum of β-methyl peltatin B was also performed through direct and long-range heteronuclear 2D NMR analysis, amending previous assignments. Key Word Index - Juniperus thurifera; Cupressaceae; methyl deoxypodophyllotoxinate; podophyllotoxinic acid; 7β-hydroxydihydrosesamin; lignans.

Preparation and cytotoxicity of podophyllotoxin derivatives lacking the lactone ring

Several cyclolignans lacking of the Iactone moiety can easily be prepared from naturally occurring lignans such as podophyllotoxin and deoxypodophyllotoxin by simple chemical transformations. Their cytotoxicity has been studied in four tumoral cell lines. Most of the compounds show similar effects in all the neoplastic systems tested, except the 3 aldehyde 9 (methyl 9-deoxy-9-oxo-α-apopicropodophyllate) and the hydrazones 16 and 17 which show a highly selective cytotoxicity towards HT-29 human colon carcinoma. Additionally, several molecular modeling studies have been done with aldehyde 9 and the correspnding saturated aldehyde 13 in comparison with podophyllotoxin.

Synthesis of (+/-)-4-Deoxypodophyllotoxin, (+/-)-Podophyllotoxin and (+/-)-Epipodophyllotoxin

6,7-Methylenedioxy-1-(3',4',5'-trimethoxyphenyl)-2-benzopyran-3-one 1 and dimethyl fumarate in acetonitrile give mostly the C-2 exo-CO2Me adduct 4 which is transformed in four steps into epipodophyllotoxin 10a.Attempted addition of dimethyl maleate to 1 p

Regioselective Suprafacial 1,5-Hydrogen Shifts in o-Quinodimethanes; a Route to 4-Deoxypodophyllotoxin

The o-quinodimethane intermediate (4a) with cis-CO2Me groups undergoes regioselective 1,5-hydrogen shift to the cis-dihydronaphthalene (5a) whilst its trans-isomer (9a) gives both 1,5-hydrogen shift products (6a) and (7a); (5a) is readily converted into 4

A Stereo- and Regiocontrolled Synthesis of Podophyllum Lignans

A Diels-Alder adduct of an isobenzofuran (generated in situ) and dimethyl acetylenedicarboxylate is converted by a series of controlled reductions and isomerizations to the lignans deoxy- and isodeoxypodophyllotoxin in seven stages.