72101-44-1

Basic information

• Product Name: 6-Chloro-9,N-bis(trimethylsilyl)-9H-purin-2-amine
• Synonyms: 6-Chloro-9,N-bis(trimethylsilyl)-9H-purin-2-amine
• CAS NO: 72101-44-1
• Molecular Formula: C₁₁H₂₀ClN₅Si₂
• Molecular Weight: 0
• Mol File: 72101-44-1.mol
• Article Data: 3

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-Chloro-9,N-bis(trimethylsilyl)-9H-purin-2-amine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-9,N-bis(trimethylsilyl)-9H-purin-2-amine(72101-44-1)
• EPA Substance Registry System: 6-Chloro-9,N-bis(trimethylsilyl)-9H-purin-2-amine(72101-44-1)

Safety Data

• Hazardous Substances Data: 72101-44-1(Hazardous Substances Data)

Usage

Abbreviation

CTMSP

Structure

Purine structure with a chloro substituent and trimethylsilyl groups attached to the nitrogen atoms

Usage

Protecting Group: Commonly used as a protecting group for amino groups in organic synthesis
Precursor: Serves as a precursor for various pharmaceuticals and biologically active compounds

Versatility

CTMSP is a versatile intermediate in chemical reactions.

Applications

Drug Development: Used in the development of new drugs and pharmaceuticals.

Value in Chemistry

Its chemical properties and reactivity make it a valuable tool in organic synthesis and medicinal chemistry.

Upstream product

• 10310-21-1 2-Amino-6-chloropurin 
• 999-97-3 1,1,1,3,3,3-hexamethyl-disilazane 

Downstream Products

• 132813-80-0 Benzoic acid (3S,5R)-5-(2-amino-6-chloro-purin-9-yl)-tetrahydro-furan-3-ylmethyl ester 
• 132813-80-0 Benzoic acid (3R,5R)-5-(2-amino-6-chloro-purin-9-yl)-tetrahydro-furan-3-ylmethyl ester 
• 118373-61-8 2-amino-6-chloro-9-(3',5'-di-O-benzoyl-2'-deoxy-2'-fluoro-β-D-arabinofuranosyl)-9H-purine 
• 197452-66-7 9-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-β-L-erythro-pentofuranos-1-yl)-2-amino-6-chloropurine 
• 197452-67-8 9-(3,5-di-O-benzoyl-2-deoxy-2,2-difluoro-α-L-erythro-pentofuranos-1-yl)-2-amino-6-chloropurine 
• 103884-98-6 9-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-guanine 
• 118373-60-7 2-amino-6-chloro-9-(3,5-di-O-benzoyl-2-deoxy-2-fluoro-α-D-arabinofuranosyl)-9H-purine 

Relevant articles and documents

Structure-activity relationships of 2'-deoxy-2',2'-difluoro-L-erythro- pentofuranosyl nucleosides

Following the recent discoveries that some L-nucleosides are more or equal potent than their D-counterparts, we synthesized 2'-deoxy-2',2'- difluoro-L-erythro-pentofuranosyl nucleosides as potential antiviral agents. The target compounds were synthesized via the key intermediates 7a or 7b from L-gulono γ-lactone. Compound 2 was oxidatively cleaved and coupled with ethyl bromodifluoroacetate in the presence of activated zinc under Reformatsky conditions to obtain a diastereomeric mixture of 4(R) and 4(S), in a 4:1 ratio. The major 4(R) isomer was cyclized and treated appropriately to obtain the mesylate 8a or 8b, which was condensed with various silyl- protected pyrimidines. Condensation of the alcohol 7a or 7b with 6- chloropurine under Mitsunobu conditions afforded the 6-chloropurine analogs 53a or 53b and 54a or 54b. Further treatment of the compounds 53a, 54a and 53b, 54b afforded the inosine and adenine derivatives 57-60, respectively. The condensation of 2-amino-6-chloropurine with compound 8a and subsequent treatment with 2-mercaptoethanol/sodium methoxide afforded the guanine analogs 63 and 64. All of the synthesized nucleosides 31-52, 57-60, 63, and 64 were evaluated for antiviral activity and for cellular toxicity. Adenine derivative 57 showed a moderate activity against HIV-1 in PBM cells (3.4 μM). None of the other compounds showed any significant activities against HIV-1, HBV, HSV-1, HSV-2, and toxicity in Veto, CEM, and PBM cell lines up to 100 μM. The X-ray structure of the 5-iodocytosine analog showed a 2'- exo/3'-endo conformation for the carbohydrate moiety, which is different from those of the biologically active compounds (-)-FTC and L-FMAU.

Guanine, thioguanine, and related nucleosides by the mercuric cyanide--silyl method. An improved synthesis of -2'-deoxythioguanosine.

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