1056674-35-1

Basic information

• Product Name: 5,6-di-O-benzyl-2,3-dideoxy-D-glucono-1,4-lactone
• Synonyms: 5,6-di-O-benzyl-2,3-dideoxy-D-glucono-1,4-lactone
• CAS NO: 1056674-35-1
• Molecular Weight: 326.392
• Mol File: 1056674-35-1.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 5,6-di-O-benzyl-2,3-dideoxy-D-glucono-1,4-lactone(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-di-O-benzyl-2,3-dideoxy-D-glucono-1,4-lactone(1056674-35-1)
• EPA Substance Registry System: 5,6-di-O-benzyl-2,3-dideoxy-D-glucono-1,4-lactone(1056674-35-1)

Safety Data

• Hazardous Substances Data: 1056674-35-1(Hazardous Substances Data)

Upstream product

• 112031-55-7 5,6-di-O-benzyl-3-deoxy-1,2-O-isopropylidene-α-D-glucofuranoside 
• 1056674-18-0 methyl 5,6-di-O-benzyl-3-deoxy-α-D-glucofuranoside 
• 1067648-38-7 imidazole-1-carbothioic acid O-(5-(1,2-bisbenzyloxyethyl)-2-methoxytetrahydrofuran-3-yl) ester 
• 1079398-63-2 methyl 5,6-di-O-benzyl-3-deoxy-D-glucofuranoside 
• 1056674-30-6 (2S,5S)-2-((R)-1,2-bis(benzyloxy)ethyl)-5-methoxytetrahydrofuran 
• 1067648-39-8 methyl 5,6-di-O-benzyl-2,3-dideoxy-D-glucofuranoside 

Downstream Products

• 1067648-40-1 5,6-di-O-benzyl-2,3-dideoxy-2-methyl-D-glucono-1,4-lactone 
• 1056674-40-8 (3S,5S)-5-((R)-1,2-bis(benzyloxy)ethyl)-3-isopropyldihydrofuran-2(3H)-one 
• 1056674-54-4 (3S,5S)-5-[(1R)-2-(benzyloxy)-1-hydroxyethyl]-3-isopropyldihydrofuran-2(3H)-one 
• 1000045-28-2 (3S,5S)-5-[(1S)-1-azido-2-benzyloxyethyl]-3-isopropyldihydrofuran-2-one 
• 1067648-42-3 2,3-dideoxy-6-O-(3,5-difluorobenzyl)-2-methyl-D-glucono-1,4-lactone 
• 1067648-43-4 5-azido-2,3,5-trideoxy-6-O-(3,5-difluorobenzyl)-2-methyl-L-idono-1,4-lactone 
• 1067648-48-9 (2R,4S,5S)-5-azido-6-(3,5-difluorobenzyloxy)-4-hydroxy-2-methylhexanoic acid cyclopropylamide 
• 1056670-82-6 (2S,4S,5S)-5-amino-6-benzyloxy-4-hydroxy-2-isopropyl-hexanoic acid ((S)-1-benzylcarbamoyl-2-methyl-propyl)amide 
• 1067648-90-1 (2S,4S,5S)-5-amino-6-benzyloxy-4-hydroxy-2-isopropyl-hexanoic acid ((S)-1-benzylcarbamoyl-2-methyl-butyl)-amide 
• 1056674-63-5 (2S,4S,5S)-5-azido-6-benzyloxy-4-hydroxy-2-isopropyl-hexanoic acid ((S)-1-benzylcarbamoyl-2-methyl-propyl)amide 
• 1067648-89-8 (2S,4S,5S)-5-azido-6-benzyloxy-4-hydroxy-2-isopropyl-hexanoic acid ((S)-1-benzylcarbamoyl-2-methyl-butyl)-amide 
• 1056670-83-7 (2S,4S,5S)-5-amino-6-benzyloxy-4-hydroxy-2-isopropyl-hexanoic acid ((S)-1-benzylcarbamoyl-2-methyl-propyl)amide trifluoroacetate 
• 1067648-25-2 methanesulphonic acid 3-[(1S,2S,4S)-4-((S)-1-benzylcarbamoyl-2-methyl-propylcarbamoyl)-1-benzyloxymethyl-2-hydroxy-5-methyl-hexylcarbamoyl]-5-((R)-1-phenyl-ethylcarbamoyl)-phenyl ester 
• 1067648-24-1 N-[(1S,2S,4S)-4-((S)-1-benzylcarbamoyl-2-methylpropylcarbamoyl)-1-benzyloxymethyl-2-hydroxy-5-methylhexyl]-5-(methanesulphonylmethylamino)-N'-((R)-1-phenylethyl)isophthalamide 

Relevant articles and documents

Synthesis of potent BACE-1 inhibitors incorporating a hydroxyethylene isostere as central core

We herein describe the design and synthesis of a series of BACE-1 inhibitors incorporating a P1-substituted hydroxylethylene transition state isostere. The synthetic route starting from commercially available carbohydrates yielded a pivotal lactone intermediate with excellent stereochemical control which subsequently could be diversified at the P1-position. The final inhibitors were optimized using three different amines to provide the residues in the P2′-P3′ position and three different acids affording the residues in the P2-P3 position. In addition we report on the stereochemical preference of the P1′-methyl substituent in the synthesized inhibitors. All inhibitors were evaluated in an in vitro BACE-1 assay where the most potent inhibitor, 34-(R), exhibited a BACE-1 IC50 value of 3.1 nM.

NEW COMPOUNDS

The invention provides compounds of the formula I wherein Q is aryl or heterocyclyl any of which is optionally substituted; Z is O, S, NRa or S(=O)p; Y is NH, NHNH, CH2NH, O, S or S(=O)p; n is 0, 1, 2 or 3; m is 0, 1 or 2; p is 1 or 2; Ra is H or C1-C4alkyl; R1 is hydrogen, C1-C6alkyl, C0-C3alkanediylC3-C7cycloalkyl, C0-C3alkanediylaryl or C0- C3alkanediylheterocyclyl; R2 is hydrogen or C1-C6alkyl; X' is hydrogen, fluoro, hydroxy, amino or C1-C6alkoxy; X" is hydrogen, or when X' is fluoro, then X" may also be fluoro; R3is C1-C6alkyl; R4' is C1-C6alkyl; R4" is H or C1-C6alkyl; or R4' and R4" together with the carbon atom to which they are attached define a C3-C6cycloalkyl; W is C1-C6alkyl, C3-C7cycloalkyl, aryl or heterocyclyl any of which is optionally substituted; or a pharmaceutically acceptable salt, hydrate or N-oxide thereof. The compounds of the invention are inhibitors of aspartyl proteases such as renin and are among other things useful for the treatment of conditions associated with activities of the RAS, such as hypertension, heart failure and renal insufficiency.