115509-74-5

Basic information

• Product Name: 1⁽³⁾,2-O-cyclohexylidene-3⁽¹⁾,6⁽⁴⁾-di-O-benzyl-sn-myoinositol
• Synonyms: 1⁽³⁾,2-O-cyclohexylidene-3⁽¹⁾,6⁽⁴⁾-di-O-benzyl-sn-myoinositol
• CAS NO: 115509-74-5
• Molecular Weight: 440.536
• Mol File: 115509-74-5.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1⁽³⁾,2-O-cyclohexylidene-3⁽¹⁾,6⁽⁴⁾-di-O-benzyl-sn-myoinositol(CAS DataBase Reference)
• NIST Chemistry Reference: 1⁽³⁾,2-O-cyclohexylidene-3⁽¹⁾,6⁽⁴⁾-di-O-benzyl-sn-myoinositol(115509-74-5)
• EPA Substance Registry System: 1⁽³⁾,2-O-cyclohexylidene-3⁽¹⁾,6⁽⁴⁾-di-O-benzyl-sn-myoinositol(115509-74-5)

Safety Data

• Hazardous Substances Data: 115509-74-5(Hazardous Substances Data)

Upstream product

• 108-94-1 cyclohexanone 
• 100-44-7 benzyl chloride 
• 34361-60-9 1,2:4,5-dicyclohexylidene-myo-inositol 
• 6763-47-9 rac-1,2-O-cyclohexylidene-myo-inositol 
• 1122-84-5 1-ethoxycyclohexene 
• 87-89-8 D-myo-inositol 
• 23486-92-2 3,6-di-O-benzyl-1,2:4,5-di-O-cyclohexylidene-D(L)-myo-inositol 
• 111408-68-5 3,6-di-O-benzyl-D/L-myo-inositol 
• 104826-13-3 1D-4,5-di-O-allyl-3,6-di-O-benzyl-1-l-menthoxyacetyl-myo-inositol 
• 104826-12-2 (+/-)-4,5-di-O-allyl-3,6-di-O-benzyl-1,2-O-cyclohexylidene-myo-inositol 
• 98925-52-1 (+/-)-5,6-di-O-allyl-1,4-di-O-benzyl-myo-inositol 
• 104873-73-6 1L-5,6-di-O-allyl-1,4-di-O-benzyl-myo-inositol 
• 191488-21-8 1D-1-O-(L-O-acetylmandelyl)-3,6-di-O-benzyl-4,5-di-O-(p-methoxybenzyl)-myo-inositol 
• 111465-38-4 D-3,6-di-O-benzyl-4,5-bis-O-(p-methoxybenzyl)-myo-inositol 

Downstream Products

• 113084-86-9 1L-1,4-di-O-benzyl-2,3-O-cyclohexylidene-5,6-di-O-(p-methoxybenzyl)-myo-inositol 
• 58526-04-8 1D-1,4-di-O-benzyl-2,3-O-cyclohexylidene-myo-inositol 
• 57029-86-4 3,4,5,6-tetra-O-benzyl-1,2-O-cyclohexylidene-sn-myo-inositol 
• 57029-85-3 1,4,5,6-tetra-O-benzyl-2,3-O-cyclohexylidene-sn-myo-inositol 
• 24558-77-8 3,4,5,6-tetra-O-benzyl inositol 
• 28140-40-1 1,4,5,6-tetra-O-benzyl-myo-inositol 
• 111331-59-0 DL-1,4-Di-O-benzyl-5,6-bis-O-(4-methoxybenzyl)-myo-inositol 
• 111465-38-4 D-3,6-di-O-benzyl-4,5-bis-O-(p-methoxybenzyl)-myo-inositol 
• 111331-59-0 1D-1,4-di-O-benzyl-5,6-di-O-(p-methoxybenzyl)-myo-inositol 
• 191488-22-9 1L-1-O-(L-O-acetylmandelyl)-3,6-di-O-benzyl-4,5-di-O-(p-methoxybenzyl)-myo-inositol 
• 191488-21-8 1D-1-O-(L-O-acetylmandelyl)-3,6-di-O-benzyl-4,5-di-O-(p-methoxybenzyl)-myo-inositol 
• 272775-91-4 1L-1-azido-3,6-di-O-benzyl-1-deoxy-myo-inositol 
• 330801-89-3 1L-2-O-acetyl-1-azido-3,6-di-O-benzyl-1-deoxy-myo-inositol 
• 330801-87-1 1L-1-azido-3,6-di-O-benzyl-1-deoxy-4,5-di-O-(p-methoxybenzyl)-scyllo-inositol 

Relevant articles and documents

Total synthesis of spicamycin

The first total synthesis of one of the spicamycin congeners, SPM VIII (3), is described. A preliminary model study for construction of the characteristic N-glycoside linkage in spicamycin using tetra-O-benzyl-β-D-mannopyranosylamine (13) and halopurines 5 revealed that Pd-catalyzed conditions successfully provided the coupling products 14 and 15 in good yields. It was also shown that thermal anomerization of the N-glycosides easily occurred, which resulted in the predominant formation of the β-anomer as the thermodynamically favored compound, and the activation energy of anomerization of 15 was estimated to be ca. 30 kcal/mol. The novel aminoheptose unit of spicamycin 6 was prepared stereoselectively by carbon elongation of an acyclic aldehyde, prepared by ring cleavage reaction of a highly functionalized cyclohexane derived from naturally abundant myo-inositol. The Pd-catalyzed coupling reaction of the β-heptopyranosylamine 6 with protected 6-chloropurine 5d, followed by deprotection, provided spicamycin amino nucleoside 2, whose condensation with dodecanoylglycine completed the total synthesis of 3. This study confirmed the proposed unique structure of a novel nucleoside antibiotic.

The absolute configuration and optical purity of (-)- and (+)-1,2:4,5-di-O-cyclohexylidene-myo-inositols

The absolute configurations of (-)- and (+)-1,2:4,5-di-O-cyclohexylidene-myo-inositols are derived as 1D- and 1L-1,2:4,5-di-O-cyclohexylidene-myo-inositols respectively, and are reverse of the most recent literature assignments.

The synthesis of DL-1-(hexadecanoyloxy)methyl- and 1-O-hexadecanoyl-inositols as potential inhibitors of phospholipase C

The synthesis of racemic analogues of phosphatidylinositol (PI) and phosphatidylinositol 4,5-bisphosphate (PIP2) starting from myo-inositol is described. Inositol derivatives with and without homologation at C(1) and with and without ionic grou