54783-95-8

Usage

InChI:InChI=1/C15H32N4O5/c1-6(16)8-5-4-7(17)15(23-8)24-13-9(18)11(20)14(22-3)10(19-2)12(13)21/h6-15,19-21H,4-5,16-18H2,1-3H3/t6-,7+,8-,9-,10-,11-,12+,13+,14+,15+/m0/s1

Upstream product

• 78561-47-4 1,2',6'-tri-N-benzyloxycarbonyl-4-N-ethoxycarbonylfortimicin B 
• 76801-48-4 2',6'-di-N-benzyloxycarbonyl-2-epi-fortimicin B 1,2-(2-benzyloxy)oxazoline 4,5-carbamate 
• 76801-55-3 1,2',6'-tri-N-acetyl-2-epi-fortimicin B 4,5-carbamate 
• 79198-79-1 ((3R,5S,6R)-4-Benzyloxycarbonylamino-3-{(2R,3R)-3-benzyloxycarbonylamino-6-[(S)-1-(2,2,2-trichloro-ethoxycarbonylamino)-ethyl]-tetrahydro-pyran-2-yloxy}-2,5-dihydroxy-6-methoxy-cyclohexyl)-methyl-carbamic acid 2,2,2-trichloro-ethyl ester 
• 78740-86-0 1,2'-di-N-benzyloxycarbonyl-6'-N-(2,2,2-trichloroethoxycarbonyl)-fortimicin B-4,5-carbamate 
• 79198-78-0 1,2'-di-N-benzyloxycarbonyl-6'-N-chlorofortimicin B-4,5-carbamate 
• 78740-88-2 1,2'-di-N-benzyloxycarbonyl-6'-iminofortimicin B-4,5-carbamate 
• 78740-87-1 1,2-di-N-benzyloxycarbonyl-6'-epi-fortimicin B-4,5-carbamate 
• 74615-80-8 1-O-acetyl-2,6-bis-N-(2,4-dinitrophenyl)-6-epi-purpurosamine B 
• 102735-31-9 1-O-acetyl-2,6-bis(2,4-dinitrophenylamino)-2,3,4,6,7-pentadeoxy-L-lyxo-heptapyranose 
• 754135-43-8 Acetic acid (2R,3R,6S)-3-amino-6-((S)-1-amino-ethyl)-tetrahydro-pyran-2-yl ester 
• 74615-85-3 1,2:4,5-di-N,O-carbonylfortamine B 
• 74615-81-9 2,6-bis(2,4-dinitrophenylamino)-2,3,4,6,7-pentadeoxy-L-lyxo-heptapyranosyl chloride 

Downstream Products

• 66962-55-8 1,2',6'-tri-N-benzyloxycarbonyl-6'-epi-fortimicin B 
• 66962-55-8 1,2',6'-tri-N-(benzyloxycarbonyl)fortimicin B 
• 66962-55-8 1,2',6'-tri-N-benzyloxycarbonyl-2-epi-fortimicin B 
• 74615-82-0 di-N-acetylfortamine B 
• 111170-95-7 2,5-di-O-benzoyl-1,4-bisfortamine B 
• 64307-87-5 tetra-N-acetylfortimicin B 
• 67010-18-8 2-epi-fortimicin A tetrahydrochloride 
• 66962-56-9 1,2',6',2''-tetra-N-benzyloxycarbonyl-2-epi-fortimicin A 
• 66768-12-5 2-epi-fortimicin A disulfate 
• 76801-51-9 1,2',6',2''-tetra-N-benzyloxycarbonyl-2-O-(N-benzyloxycarbonyl)glycyl-2-epi-fortimicin A 
• 76801-64-4 1,2',6',2''-tetra-N-benzyloxycarbonyl-2-O-(N-benzyloxycarbonyl)glycyl-5-deoxy-2-epi-fortimicin A 
• 75721-57-2 1,2',6',2''-tetra-N-benzyloxycarbonyl-5-deoxy-2-epi-fortimicin A 
• 78853-72-2 5-deoxy-2-epi-fortimicin A disulfate 
• 76801-61-1 2-O-glycyl-2-epi-fortimicin A pentahydrochloride 

Relevant academic research and scientific papers

The Total Synthesis of Antibiotic Fortimicin B

The total synthesis of antibiotic fortimicin B (1b) is described.The sugar component of 1b: 6-epi-purpurosamine B was converted to the sugar chloride: 2,6-bis(2,4-dinitrophenylamino)-2,3,4,6,7-pentadeoxy-β-L-lyxoheptopyranosyl chloride (5).The aminocyclit

2-epi-FORTIMICIN B. PARTICIPATION OF 1-N-BENZYLOXYCARBONYLAMINO AND 1-ACETAMIDO GROUPS IN SOLVOLYSIS OF 2-O-(METHYLSULFONYL)FORTIMICIN B DERIVATIVES

Synthesis of 2-epi-fortimicin B has been accomplished by processes involving solvolyses of both 1-N-benzyloxycarbonyl- and 1-N-acetyl-2-O-(methylsulfonyl)fortimicins B, which occur with participation of the carbonyl oxygen atoms of the 1-N-acyl groups.The

SYNTHESIS OF ANTIBIOTIC FORTIMICIN B

Aminocyclitol antibiotic fortimicin B has been synthesized by condensation of 2,6-bis-N-(2,4-dinitrophenyl)-α-6-epi-purpurosaminyl chloride and 1,2:4,5-di-N,O-carbonylfortamine B, followed by removal of all protective groups.

4-N-Acylfortimicin B derivatives and the chemical conversion of fortimicin B to fortimicin A

This invention provides 4-N-acylfortimicin B derivatives of the structure STR1 wherein R is acyl, aminoacyl, N-monoloweralkylminoacyl, N,N-diloweralkylaminoacyl, hydroxy-substituted aminoacyl, or substituted aminoacyl of the formula STR2 where R1 is an acyl radical derived from an amino acid or a short peptide, and the pharmaceutically acceptable salts thereof. The compounds are useful as intermediates for preparing 4-N-alkyl or substituted alkylfortimicin B derivatives. In addition to their utility as intermediates, some of the compounds of this invention are also useful as antimicrobial agents.

Fortimicin AK

A new fortimicin, fortimicin AK. The compound is coproduced in the fermentation of Micromonospora olivoasterospora ATCC No. 21819, 31009 or 31010 along with fortimicin A, fortimicin B isofortimicin, fortimicin E and a number of other minor factors. The compound is useful as an intermediate in synthesizing fortimicin AK derivatives which are useful as antibiotics.

2-N-acyl and alkyl 6-epi-fortimicin B and derivatives

2'-N-Acyl and alkyl-6'-epi-fortimicin B and fortimicin B derivatives represented by the formula STR1 wherein: R is acyl, hydroxyacyl, aminoacyl, N-monoloweralkylamino, N,N-diloweralkylaminoacyl, hydroxy-substituted aminoacyl, an amino acid residue, loweralkyl, aminoloweralkyl, hydroxyloweralkyl, N-loweralkylaminoloweralkyl, N,N-diloweralkylaminoloweralkyl, aminohydroxyloweralkyl, N-loweralkylaminohydroxyloweralkyl or N,N-diloweralkylaminohydroxyloweralkyl; and R1 is acyl, aminoacyl, N-monoloweralkylaminoacyl, N,N-diloweralkylaminoacyl, hydroxy-substituted aminoacyl, an amino acid residue, hydroxyacyl loweralkyl, aminoloweralkyl, hydroxyloweralkyl, N-loweralkylaminoloweralkyl, N,N-diloweralkylaminoloweralkyl, aminohydroxyloweralkyl, N-loweralkylaminohydroxyloweralkyl, N,N-diloweralkylaminohydroxyloweralkyl or hydrogen; R2 is loweralkyl; and R3 is hydrogen or loweralkyl; and the pharmaceutically acceptable salts thereof; pharmaceutical compositions containing the compounds; and methods of making and using the compounds. The compounds are antibiotics.

6'-Epi-fortimicin A and B derivatives

6'-Epi-fortimicin A and B derivatives represented by the formula STR1 wherein R1 is hydrogen or loweralkyl, R2 is hydrogen or loweralkyl and R3 is selected from the group consisting of hydrogen, loweralkyl, aminoloweralkyl, N-loweralkylaminoloweralkyl, N,N-diloweralkylaminoloweralkyl, aminohydroxyloweralkyl, N-loweralkylaminohydroxyloweralkyl, hydroxyloweralkyl, acyl, aminoacyl, hydroxyacyl, N-monoloweralkylaminoacyl, N,N-diloweralkylaminoacyl, hydroxy-substituted aminoacyl or an amino acid residue; the pharmaceutically acceptable salts thereof; intermediates useful in their preparation, compositions employing the compounds; and methods of using the compounds. The compounds are useful as antibiotics.

2'-N-ACYLFORTIMICINS AND 2'-N-ALKYLFORTIMICINS via THE ISOFORTIMICIN REARRANGEMENT

Fortimicin A and a number of 4-N-acylfortimicins B, although stable as either the fully protonated hydrochloride of sulfate salts, undergo degradation as the free bases in aqueous solution.Detailed studies with fortimicin A and 4-N-acetylfortimicin B have