64339-87-3

Basic information

• Product Name: Benzamide, N-(trimethylsilyl)-N-[2-[(trimethylsilyl)oxy]-4-pyrimidinyl]-
• CAS NO: 64339-87-3
• Molecular Formula: C17H25N3O2Si2
• Molecular Weight: 359.575
• Mol File: 64339-87-3.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: Benzamide, N-(trimethylsilyl)-N-[2-[(trimethylsilyl)oxy]-4-pyrimidinyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzamide, N-(trimethylsilyl)-N-[2-[(trimethylsilyl)oxy]-4-pyrimidinyl]-(64339-87-3)
• EPA Substance Registry System: Benzamide, N-(trimethylsilyl)-N-[2-[(trimethylsilyl)oxy]-4-pyrimidinyl]-(64339-87-3)

Safety Data

• Hazardous Substances Data: 64339-87-3(Hazardous Substances Data)

Upstream product

• 10416-59-8 N,O-bis-(trimethylsilyl)-acetamide 
• 26661-13-2 4-N-benzoylcytosine 
• 26661-13-2 N⁴-Benzoylcytosine 
• 98-88-4 benzoyl chloride 
• 4039-32-1 lithium hexamethyldisilazane 
• 21149-38-2 2,2,2-trifluoro-N,N-bis(trimethylsilyl)-acetamide 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 
• 25561-30-2 N,O-Bis(trimethylsilyl)trifluoroacetamide 
• 107-46-0 Hexamethyldisiloxane 

Downstream Products

• 23624-64-8 N⁴-benzoyl-1-(2’,3’,5’-tri-O-benzoyl-β-D-ribofuranosyl)-cytosine 
• 31652-74-1 2',3',5'-tri-O-benzoyl-L-cytidine 
• 189829-23-0 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-(4-benzoylamino-2-oxo-2H-pyrimidin-1-yl)-5-(2,2,2-trifluoro-acetylamino)-tetrahydro-pyran-4-yl ester 
• 446862-77-7 N⁴-benzoyl-5'-O-tert-butyldiphenylsilyl-2',3'-di-O-acetyl-4'-C-(p-toluenesulfonyl)oxymethylcytidine 
• 919076-82-7 (2R,5R)-{2-[(2,2-dimethyl-1,1-diphenyl-1-silapropoxy)methyl]-5-[2-oxo-4-(phenylcarbonylamino)hydropyrimidinyl]oxolan-2-yl}methyl acetate 
• 817204-32-3 (2R,3R,4R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4-fluoro-4-methyltetrahydrofuran-3-yl benzoate 
• 1445381-44-1 (2R,3R,5R)-5-(4-benzamido-2-oxopyrimidin-1(2H)-yl)-2-((benzoyloxy)methyl)-4,4-difluorotetrahydrofuran-3-yl benzoate 
• 1311109-53-1 N⁴-benzoyl-1-(2’,3’,4’,6’-tetra-O-acetyl-β-D-galactopyranosyl)-cytosine 
• 97626-95-4 N⁴-benzoyl-1-(2’,3’,5’-tri-O-acetyl-β-D-ribofuranosyl)-cytosine 
• 3624-41-7 N⁴-benzoyl-1-(2’,3’,4’,6’-tetra-O-acetyl-β-D-glucopyranosly)-cytosine 
• 31501-22-1 N⁴-benzoyl-1-(3',5'-di-O-benzoyl-2'-deoxy-β-D-ribofuranosyl)-cytosine 

Relevant articles and documents

Stereoselective N-glycosylation with N4-acyl cytosines and efficient synthesis of gemcitabine

Through systematical comparison of various N4-protected cytosine derivatives in the glycosylation step of gemcitabine synthesis, highly beta-stereoselective and high yielding TBAI catalyzed N-glycosylation was achieved with N4-Bz cytosine and anomeric mixture of 2,2‘-difluororibose mesylate donor. The subsequent global deprotection gave gemcitabine efficiently. Meanwhile, the anomeric chloride intermediate and fluoride-displaced side products of this N-glycosylation were identified, too. This new glycosylation method reveals the importance of N4-protection in the stereoselective preparation of pyrimidine nucleoside, also provides a potential alternative to current industrial process to gemcitabine.

A general method for N-glycosylation of nucleobases promoted by (p-Tol)2SO/Tf2O with thioglycoside as donor

Based on a preactivation strategy using the (p-Tol)2SO/Tf2O system, a series of nucleosides were synthesized by coupling various thioglycosides with pyrimidines and purines under mild conditions. High yields and excellent β-stereoselectivities were obtained with either armed or disarmed N-glycosylation donors by tuning the amount of (p-Tol)2SO additive.

The triphosphate of β-d-4′-C-ethynyl-2′,3′-dideoxycytidine is the preferred enantiomer substrate for HIV reverse transcriptase

The enantioselective synthesis of the β-d (1) enantiomer of 4′-C-ethynyl-2′,3′-dideoxycytidine confirms an earlier stereochemical assignment that was strictly based on the ability of HIV reverse transcriptase and its M184V mutant to discriminate between t