33584-87-1

Basic information

• Product Name: Benzaldehyde, 3-chloro-4,5-bis(phenylmethoxy)-
• Synonyms: 3,4-dibenzyloxy-5-chlorobenzaldehyde;3,4-Dibenzyloxy-5-chlor-benzaldehyd;5-chloro-3,4-dibenzyloxybenzaldehyde;5-Chlor-3,4-dibenzyloxybenzaldehyd
• CAS NO: 33584-87-1
• Molecular Formula: C21H17ClO3
• Molecular Weight: 352.81100
• Mol File: 33584-87-1.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: Benzaldehyde, 3-chloro-4,5-bis(phenylmethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzaldehyde, 3-chloro-4,5-bis(phenylmethoxy)-(33584-87-1)
• EPA Substance Registry System: Benzaldehyde, 3-chloro-4,5-bis(phenylmethoxy)-(33584-87-1)

Safety Data

• Hazardous Substances Data: 33584-87-1(Hazardous Substances Data)

Upstream product

• 121-33-5 vanillin 
• 19463-48-0 5-chlorovanillin 
• 34098-18-5 5-chloro-3,4-dihydroxybenzaldehyde 
• 100-39-0 benzyl bromide 

Downstream Products

• 765950-75-2 3,4-dibenzyloxy-5-chlorophenol 
• 765950-76-3 1,2-dibenzyloxy-3-chloro-5-(tert-butyldimethylsilyloxy)benzene 
• 682744-25-8 4-bromo-3-chloro-1,2-dibenzyloxy-5-(tert-butyldimethylsilyloxy)benzene 
• 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 
• 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 
• 765950-80-9 (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 
• 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 
• 765950-78-5 (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 
• 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 
• 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 

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.