765950-75-2

Basic information

• Product Name: 3,4-dibenzyloxy-5-chlorophenol
• CAS NO: 765950-75-2
• Molecular Weight: 340.806
• Mol File: 765950-75-2.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: 3,4-dibenzyloxy-5-chlorophenol(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4-dibenzyloxy-5-chlorophenol(765950-75-2)
• EPA Substance Registry System: 3,4-dibenzyloxy-5-chlorophenol(765950-75-2)

Safety Data

• Hazardous Substances Data: 765950-75-2(Hazardous Substances Data)

Upstream product

• 121-33-5 vanillin 
• 33584-87-1 3-chloro-4,5-di(phenylmethoxy)benzaldehyde 
• 19463-48-0 5-chlorovanillin 
• 34098-18-5 5-chloro-3,4-dihydroxybenzaldehyde 

Downstream Products

• 682744-26-9 (1S,4aS,8aS)-1-[(3,4-dibenzyloxy-6-tert-butyldimethylsilyloxy-2-chlorophenyl)-hydroxymethyl]-3H-2-methylene-1,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene 
• 765950-79-6 (1S,4aS,8aS)-1-[(3,4-dibenzyloxy-6-tert-butyldimethylsilyloxy-2-chlorophenyl)-hydroxymethyl]-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene 
• 765950-78-5 (4aS,6aS,12bS)-2H-9,10-dibenzyloxy-11-chloro-1,3,4,4a,5,6,6a,12b-octahydro-6a-[(phenylseleno)methyl]-4,4,12b-trimethyl-benzo[a]xanthene 
• 682744-27-0 (1S,4aS,8aS)-1-[(3,4-dibenzyloxy-2-chloro-6-hydroxyphenyl)-hydroxymethyl]-3H-2-methylene-1,4,4a,5,6,7,8,8a-octahydro-5,5,8a-trimethylnaphthalene 
• 765950-80-9 (1S,4aS,8aS)-1-[(3,4-dibenzyloxy-2-chloro-6-hydroxyphenyl)-hydroxymethyl]-1,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene 
• 765950-81-0 (4aS,6aR,12bS)-2H-9,10-dibenzyloxy-11-chloro-1,3,4,4a,5,6,6a,12b-octahydro-4,4,6a,12b-tetramethyl-benzo[a]xanthene 
• 765950-82-1 (4aS,6aS,12bS)-2H-9,10-dibenzyloxy-11-chloro-1,3,4,4a,5,6,6a,12b-octahydro-4,4,6a,12b-tetramethyl-benzo[a]xanthene 
• 682744-25-8 4-bromo-3-chloro-1,2-dibenzyloxy-5-(tert-butyldimethylsilyloxy)benzene 

Relevant articles and documents

Total syntheses of (+)-chloropuupehenone and (+)-chloropuupehenol and their analogues and evaluation of their bioactivities

Tetracyclic pyrans (+)-chloropuupehenone (1) and (+)-chloropuupehenol (5) and its C8-R-isomer (+)-3 were synthesized via a one-pot condensation of 1-chloro-2-lithio-3,5,6-tris(tert-butyldimethylsilyloxy)benzene (8) with (4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene-1- carboxaldehyde (7). The major condensation product, (4aS,6aR,12bS)-2H-9,10- bis(tert-butyldimethylsilyloxy)-11-chloro-1,3,4,4a,5,6,6a,12b-octahydro-4,4,6a, 12b-tetramethyl-benzo[a]xanthene (4), after desilylation provided tetracyclic pyran (+)-(4aS,6aR,12bS)-2H-11-chloro-1,3,4,4a,5,6,6a,12b-octahydro-4,4,6a,12b- tetramethyl-benzo[a]xanthene-9,10-diol (3). At a dosage of 42 mg/rat over 8 h, pyran diol 3 inhibited the intestinal absorption of cholesterol by 71% in rats. Tetracyclic pyran 4 was also converted to o-quinone 28, which inhibited cholesteryl ester transfer protein (CETP) activity and L1210 leukemic cell viability with IC50 values of 31 and 2.4 μM, respectively. Diol (+)-5 inhibited CETP activity with an IC50 value of 16 μM. The minor condensation product, (4aS,6aS,12bS)-2H-9,10-bis(tert- butyldimethylsilyloxy)-11-chloro-1,3,4,4a,5,6,6a,12b-octahydro-4,4,6a, 12b-tetramethyl-benzo[a]xanthene (6), was transformed into (+)-5 and (+)-1. A stepwise stereoselective synthesis of (+)-1 was also developed utilizing an oxyselenylation ring-closure reaction. The synthetic sequence also produced four biologically active naturally occurring drimanic sesquiterpenes, (+)-drimane-8α,11-diol (34), (-)-drimenol (38), (+)-albicanol (39), and (-)-albicanal (31) as intermediates.