142654-28-2

Basic information

• Product Name: O-benzyl-N,N’-di-tert-butoxycarbonylhydroxylamine
• Synonyms: O-benzyl-N,N’-di-tert-butoxycarbonylhydroxylamine
• CAS NO: 142654-28-2
• Molecular Weight: 323.389
• Mol File: 142654-28-2.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: O-benzyl-N,N’-di-tert-butoxycarbonylhydroxylamine(CAS DataBase Reference)
• NIST Chemistry Reference: O-benzyl-N,N’-di-tert-butoxycarbonylhydroxylamine(142654-28-2)
• EPA Substance Registry System: O-benzyl-N,N’-di-tert-butoxycarbonylhydroxylamine(142654-28-2)

Safety Data

• Hazardous Substances Data: 142654-28-2(Hazardous Substances Data)

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 100-39-0 benzyl bromide 
• 142654-29-3 N,N’-di-tert-butoxycarbonylhydroxylamine 
• 1122-58-3 dmap 
• 79722-21-7 tert-butyl N-(benzyloxy)carbamate 

Downstream Products

• 142654-29-3 N,N’-di-tert-butoxycarbonylhydroxylamine 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 

Relevant articles and documents

Structure-activity relationships of pyrimidine nucleotides containing a 5′-α,β-methylene diphosphonate at the P2Y6 receptor

The Gq-coupled P2Y6 receptor (P2Y6R) is a component of the purinergic signaling system and functions in inflammatory, cardiovascular and metabolic processes. UDP, the native P2Y6R agonist and P2Y14R partial agonist, is subject to hydrolysis by ectonucleotidases. Therefore, we have synthesized UDP/CDP analogues containing a stabilizing α,β-methylene bridge as P2Y6R agonists and identified compatible affinity-enhancing pyrimidine modifications. A distal binding region on the receptor was explored with 4-benzyloxyimino cytidine 5′-diphosphate analogues and their potency determined in a calcium mobilization assay. A 4-trifluoromethyl-benzyloxyimino substituent in 25 provided the highest human P2Y6R potency (MRS4554, 0.57 μM), and a 5-fluoro substitution of the cytosine ring in 28 similarly enhanced potency, with >175- and 39-fold selectivity over human P2Y14R, respectively. However, 3-alkyl (31–33, 37, 38), β-D-arabinofuranose (39) and 6-aza (40) substitution prevented P2Y6R activation. Thus, we have identified new α,β-methylene bridged N4-extended CDP analogues as P2Y6R agonists that are highly selective over the P2Y14R.

Rapid synthesis of alkoxyamine hydrochloride derivatives from alkyl bromide and N,N′-Di-tert-butoxycarbonylhydroxylamine [(Boc)2NOH]

The conventional route to alkoxyamine hydrochloride derivatives is by reaction of alkyl bromides with N-hydroxyphthalimide or N-hydroxysuccinimide followed by addition of hydrazine and HCl. Transformation of an alkyl bromide to the corresponding alkoxyamine hydrochloride can be accomplished more rapidly in good yields without using hazardous hydrazine by reaction of (Boc) 2NOH (N,N′-di-tert-butoxycarbonylhydroxylamine) and alkyl bromide followed by addition of HCl. Alkoxyamine hydrochlorides are powerful reagents in organic synthesis that can be used to synthesize alkoxyimino derivatives after condensation with a ketone or aldehyde. Copyright

HETEROARYL DERIVATIVES OF MONOCYCLIC BETA-LACTAM ANTIBIOTICS

Antibacterial activity is exhibited by novel compounds having the formula where R1, R2, and M are as defined herein and X is ?(CH2)n? wherein n is 0, 1, 2, 3 or 4 or CR3R4 wherein R3 and R4 are the same or different and each is hydrogen, ?CH3 or ?C2H5 or R3 and R4 taken together with the carbon atom to which they are attached form a 3, 4, 5, 6 or 7-membered cycloalkyl ring