156350-44-6

Basic information

• Product Name: Carbonic acid benzyl ester 4-((5R,5aR,8aR)-6,9-dioxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxy-phenyl ester
• Synonyms: Carbonic acid benzyl ester 4-((5R,5aR,8aR)-6,9-dioxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxy-phenyl ester
• CAS NO: 156350-44-6
• Molecular Weight: 532.504
• Mol File: 156350-44-6.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: Carbonic acid benzyl ester 4-((5R,5aR,8aR)-6,9-dioxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxy-phenyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: Carbonic acid benzyl ester 4-((5R,5aR,8aR)-6,9-dioxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxy-phenyl ester(156350-44-6)
• EPA Substance Registry System: Carbonic acid benzyl ester 4-((5R,5aR,8aR)-6,9-dioxo-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxy-phenyl ester(156350-44-6)

Safety Data

• Hazardous Substances Data: 156350-44-6(Hazardous Substances Data)

Upstream product

• 23412-22-8 4'-benzyloxycarbonyl-4'-demethylpodophyllotoxin 
• 40505-27-9 4-demethylpodophyllotoxin 
• 501-53-1 benzyl chloroformate 
• 6559-91-7 4'-demethylepipodophyllotoxin 
• 23363-33-9 4'-demethyl-4'-O-(benzoyloxycarbonyl)epipodophyllotoxin 

Downstream Products

• 6559-91-7 4'-demethylepipodophyllotoxin 
• 183986-37-0 Carbonic acid benzyl ester 4-((5R,5aR,8aR,9R)-9-hydroxy-6-oxo-9-phenylethynyl-5,5a,6,8,8a,9-hexahydro-furo[3',4':6,7]naphtho[2,3-d][1,3]dioxol-5-yl)-2,6-dimethoxy-phenyl ester 

Relevant articles and documents

Preparation method for total synthesis of 4'-demethylepipodophyllotoxin

The invention discloses a preparation method for total synthesis of 4'-demethylepipodophyllotoxin (also named as epipodophyllotoxin). The preparation method comprises the following steps: (1) syringaldehyde (compound 1) used as an initial material and benzyl methoxyacyl used as a protective group are in favor of a chemical reaction of finally removing the protective group to obtain a target compound; (2) a chiral target object is produced by adopting an asymmetric hydrogenation reduction reaction in which a chiral ligand (s-BINAN Ru (II)) participates; and (3) a reaction of hydrogenating and deprotecting groups is also carried out in parallel while chiral catalytic hydrogenation is carried out. The reaction steps and treatment are saved, the route selection is targeted to the target compound, the production cost is low, and the environment is friendly.

Synthesis and biological evaluation of carbon-substituted C-4 derivatives of podophyllotoxin

Several C-4 carbon-substituted analogues of podophyllotoxin, 1, were prepared by treatment of 1 with allyltrimethylsilane or trimethylsilylcyanide in the presence of boron trifluoride etherate. Alternatively, carbon substituents were introduced via additions to the carbobenzyloxy-protectd C-4'-dimethylated podophyllotoxone. These 4'-dimethylated derivatives showed promising in vitro antitumour activity and were equally active against human colon cell line HT116 and two multidrug resistant cell lines. The alcohol 6 was evaluated in vivo but was found to be inactive. Several C-4 carbon-substituted analogues of podophyllotoxin, 1, were prepared by treatment of 1 with allyltrimethylsilane or trimethylsilylcyanide in the presence of boron trifluoride etherate. Alternatively, carbon substituents were introduced via additions to the carbobenzyloxy-protected C-4′-dimethylated podophyllotoxone. These 4′-dimethylated derivatives showed promising in vitro antitumour activity and were equally active against human colon cell line HT116 and two multidrug resistant cell lines. The alcohol 6 was evaluated in vivo but was found to be inactive.