CAS 91294-64-3

D-arabino-Hexose, 2-deoxy-3,4:5,6-bis-O-(1-methylethylidene)-, cyclic 1,3-propanediyl dithioacetal

Description:

D-arabino-Hexose, 2-deoxy-3,4:5,6-bis-O-(1-methylethylidene)-, cyclic 1,3-propanediyl dithioacetal, identified by CAS number 91294-64-3, is a complex organic compound characterized by its unique structural features. This substance is a derivative of D-arabino-hexose, which is a six-carbon sugar, modified to include dithioacetal functionalities that enhance its reactivity and stability. The presence of the bis-O-(1-methylethylidene) groups indicates that it has two methylethylidene protecting groups, which are typically used to shield hydroxyl groups during chemical reactions. The cyclic 1,3-propanediyl component suggests a cyclic structure that may influence the compound's stereochemistry and reactivity. Such modifications often aim to improve the compound's solubility, stability, or reactivity in various chemical environments. This compound may be of interest in synthetic organic chemistry, particularly in the development of glycosylation reactions or as an intermediate in the synthesis of more complex molecules. Its specific applications would depend on its reactivity and the context of its use in research or industrial processes.

Formula: C₁₅H₂₆O₄S₂

InChI: InChI=1S/C15H26O4S2/c1-14(2)16-9-11(18-14)13-10(17-15(3,4)19-13)8-12-20-6-5-7-21-12/h10-13H,5-9H2,1-4H3/t10-,11-,13+/m1/s1

InChI key: InChIKey=MQCXYIUIBYSRGY-WZRBSPASSA-N

SMILES: C([C@@H]1[C@](OC(C)(C)O1)([C@@]2(OC(C)(C)OC2)[H])[H])C3SCCCS3

Synonyms:

• <span class="text-smallcaps">D</span>-arabino-Hexose, 2-deoxy-3,4:5,6-bis-O-(1-methylethylidene)-, cyclic 1,3-propanediyl dithioacetal
• <span class="text-smallcaps">D</span>-arabino-Hexose, 2-deoxy-3,4:5,6-bis-O-(1-methylethylidene)-, cyclic 1,3-propanediyl mercaptal
• D-arabino-Hexose,2-deoxy-3,4:5,6-bis-O-(1-methylethylidene)-, cyclic 1,3-propanediyl mercaptal
• D-arabino-Hexose, 2-deoxy-3,4:5,6-bis-O-(1-methylethylidene)-, cyclic 1,3-propanediyl dithioacetal

2-Deoxy-3,4:5,6-di-O-isopropylidene-D-arabino-hexose Propylene Dithioacetal

CAS: 91294-64-3

Molecular weight: 334.49

Ref: 7W-GC7972

2-Deoxy-3,4:5,6-di-O-isopropylidene-D-arabino-hexose Propylene Dithioacetal

Controlled Product

CAS: 91294-64-3

Formula: C₁₅H₂₆O₄S₂

Color and Shape: Neat

Molecular weight: 334.49

Ref: TR-D232805

2-Deoxy-3,4:5,6-di-O-isopropylidene-D-arabino-hexose propane-1,3-diyl dithioacetal

CAS: 91294-64-3

The antibiotic 2-deoxy-3,4:5,6-di-O-isopropylidene-D-arabino-hexose propane-1,3-diyl dithioacetal is a shikimate analog that inhibits the shikimate pathway. It prevents the synthesis of aromatic compounds and other nitrogenous substances by inhibiting the enzyme chorismate synthase. Chorismate synthase catalyzes the conversion of 3,4:5,6-di-O-isopropylidene D-arabino hexose to chorismic acid which is then converted to shikimic acid. The antibiotic binds covalently to an active site cysteine residue on the enzyme and inhibits its activity. This inhibition blocks the production of aromatic amino acids and other nitrogenous substances required for protein synthesis in bacteria.

Formula: C₁₅H₂₆O₄S₂

Purity: Min. 95%

Molecular weight: 334.5 g/mol

Ref: 3D-MD04698