60598-98-3

Basic information

• Product Name: (+)-1,1',1''-[[(R)-2,3-Di(benzyloxy)propoxy]methylidyne]trisbenzene
• Synonyms: (+)-1,1',1''-[[(R)-2,3-Di(benzyloxy)propoxy]methylidyne]trisbenzene;[R,(+)]-1-O,2-O-Dibenzyl-3-O-trityl-L-glycerol
• CAS NO: 60598-98-3
• Molecular Formula: C₃₆H₃₄O₃
• Molecular Weight: 514.65
• Mol File: 60598-98-3.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (+)-1,1',1''-[[(R)-2,3-Di(benzyloxy)propoxy]methylidyne]trisbenzene(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-1,1',1''-[[(R)-2,3-Di(benzyloxy)propoxy]methylidyne]trisbenzene(60598-98-3)
• EPA Substance Registry System: (+)-1,1',1''-[[(R)-2,3-Di(benzyloxy)propoxy]methylidyne]trisbenzene(60598-98-3)

Safety Data

• Hazardous Substances Data: 60598-98-3(Hazardous Substances Data)

Upstream product

• 20196-70-7 (+)-(R)-2,3-bis(benzyloxy)propanal 
• 20196-69-4 1,2,5,6-tetra-O-benzyl-D-mannitol 
• 20196-71-8 (2S)-2,3-bis(benzyloxy)propanol 
• 76-83-5 trityl chloride 

Relevant articles and documents

Synthesis and antiherpetic activity of (S)-, (R)- and (±)-9-[(2,3-dihydroxy-1-propoxy)methyl]guanine, linear isomers of 2'-nor-2'-deoxyguanosine

Racemic 9-[2,3-dihydroxy-1-propoxy)methyl]guanine [(±)-iNDG], a new analogue of acyclovir (ACV) and a structural analogue of 2'-nor-2'-deoxyguanosine (2'NDG), was synthesized and found to inhibit the replication of herpes simplex virus types 1 (HSV-1) and 2 (HSV-2). Subsequently, its optical isomers, (R)- and (S)-iNDG, were prepared from chiral intermediates. The chloromethyl ethers of 1,2-di-O-benzyl-D- and -L-glycerol were made and reacted with tris(trimethylsilyl)guanine to give the 9-alkylated guanines, which were deprotected by catalytic hydrogenolysis. Against HSV-1 and HSV-2 in cell culture, (S)-iNDG was approximately 10- to 25-fold more active than the R enantiomer and had an ED50 comparable to those for ACV and 2'NDG. The inferior activity of (R)-iNDG paralleled the poor inhibition of viral DNA polymerase by its phosphorylation products. In mice infected intraperitoneally or orofacially with HSV-1 or intravaginally with HSV-2, (S)-9-[(2,3-dihydroxy-1-propoxy)methyl]guanine [(S)-iNDG] was less efficacious than 2'NDG but comparable to or more active than ACV.