488-52-8

Usage

Uses

Used in Pharmaceutical Industry:
D-Streptamine is used as a building block for the synthesis of various antibiotics, such as aminoglycosides, for their potent antibacterial properties. These antibiotics are effective against a wide range of Gram-negative and Gram-positive bacteria, making them crucial in the treatment of bacterial infections.
Used in Drug Development:
D-Streptamine is utilized as a structural component in the development of new drugs targeting specific diseases. Its unique structure allows for the creation of molecules with enhanced binding affinity and selectivity, which can be beneficial in the treatment of various medical conditions.
Used in Research and Development:
D-Streptamine serves as an important compound in the field of research and development, particularly in the study of molecular interactions and the design of novel therapeutic agents. Its unique structure and properties make it a valuable tool for understanding the mechanisms of action of various biologically active molecules.

InChI:InChI=1/C6H14N2O4/c7-1-3(9)2(8)5(11)6(12)4(1)10/h1-6,9-12H,7-8H2/t1-,2+,3?,4+,5-,6?

Upstream product

• 7380-63-4 hexaacetyl-streptamine 
• 85-17-6 streptidine 
• 50473-98-8 1,2:4,5-Dianhydro-epi-inositol 
• 53993-40-1 Hexahydro-7,8,9,12-tetrahydroxy-6,10-methano-6H-pyridazino<1,2-a><1,2>diazepin-1,4-dion 
• 53993-39-8 7,8,9,10-Tetrahydro-7,8,9,12-tetrahydroxy-6,10-methano-6H-pyridazino<1,2-a><1,2>diazepin-1,4-dion 
• 50473-95-5 1,2:4,5-Dianhydro-muco-inosit 
• 6090-94-4 (+/-)-4c,6t-dibromo-cyclohexane-1r,2t,3c,5t-tetraol 
• 13257-58-4 (+/-)-1,5-dibromo-2,3,4,6-tetra-O-acetyl-1,5-dideoxy-asymm.-inositol 
• 53993-34-3 DL-1,2-anhydro-4,6-dideoxy-4,6-hydrazo-myo-inositol 
• 39078-11-0 cis-trisoxirane 
• 53993-36-5 1a,11,12,12a-Tetrahydro-12,13-dihydroxy-(1aβ,2α,11α,12α,12aβ,13R*)-2,11-methano-2H-oxireno<4,5><1,2>diazepino<1,2-b>phthalazin-4,9-dion 
• 53993-37-6 8,9,10,11-Tetrahydro-8,9,10,14-tetrahydroxy-7,11-methano-7H-<1,2>diazepino<1,2-b>phthalazin-5,13-dion 
• 16703-84-7 DL-2,4-Hydrazo-2,4-didesoxy-chiro-inosit 
• 87-89-8 D-myo-inositol 

Downstream Products

• 94346-17-5 4t,6t-bis-dimethylamino-cyclohexane-1r,2t,3c,5c-tetraol 
• 31087-84-0 4t,6t-bis-benzyloxycarbonylamino-cyclohexane-1r,2t,3c,5c-tetraol 
• 6931-65-3 N.N'-diacetyl-streptamine 

Relevant academic research and scientific papers

Polyfunctionalised Cyclohexanes from Dianhydroinositols. cis-1,3(1,4)-Inosadiamines from Benzene

The preparative value of the dianhydroinositols 4 - 6, which are readily available from benzene, for the total synthesis of cis-1,4- and cis-1,3-disubstituted cyclohexanetetrols is demonstrated.With monovalent reagents (H2O, HI, NaN3, NH2NH2) the twofold epoxide opening proceeds regioselectively (1,4-disubstitution) yielding the muco- and chiro-cyclohexane derivatives 9, 17, and 26.With hydrazine and N,N'-dimethylhydrazine as 1,2-dinucleophiles the cis-1,3-inosadiamines 7 g (5-epistreptamine) and 16 g, j (2-epistreptamine, actinamine) are obtained from 4/5 in good yields (75 - 90percent).From the less symmetrical 6, however, only the mixture of 25 g (streptamine) and 27 g is produced in modest yield (ca. 50percent).The epoxide opening reactions starting from 4 - 6 are kinetically so similar that a selective opening is not possible.

Streptamine from Benzene - An Efficient Synthesis of cis-Inosadiamines-(1,3) and cis-Deoxyinosadiamines-(1,3)

Efficient syntheses for cis-inosadiamines-(1,3) and cis-deoxyinosadiamines-(1,3) start out from 1,2-anhydro-4,6-dideoxy-4,6-hydrazo-myo-inositol (14a), which is selectively produced from cis-"benzene trioxide" (1) and hydrazine.Under hydrolysis conditions within wide pH-limits aziridine formation (15a) prevails; only in strongly alkaline solution uniform epoxide opening (C-2) occurs yielding the precursor (5a) of the 2,4-diamino-2,4-dideoxy-chiro-inositol (6a).By "masking" the hydrazo bridge (19a, 21) C-4-substitution is enforced (20a, 22) paving the way to 1,3-diamino-1,3-dideoxy-scyllo-inositol (2, steptamine), which is obtained in reasonable yields.Hydrazine (24a), phenylmethanethiol (26a), hydrochloric and hydrobromic acid (30a, d) add regiospecifically to 14a at C-4. 1,3-Diamino-1,3,5-trideoxy-scyllo-inositol (3,5-deoxystreptamine) and DL-2,4-diamino-1,2,4-trideoxy-chiro-inositol (33a) are quantitatively formed in the catalytic hydrogenation of 14a in neutral to acidic and basic solution, resp.