1214020-75-3

Basic information

• Product Name: 3-(ALLYLOXY)-4,5,6-TRIS(BENZYLOXY)-1,2-CYCLOHEXANEDIOL
• Synonyms: 3-(ALLYLOXY)-4,5,6-TRIS(BENZYLOXY)-1,2-CYCLOHEXANEDIOL
• CAS NO: 1214020-75-3
• Molecular Formula: C30H34O6
• Molecular Weight: 490.59
• Mol File: 1214020-75-3.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3-(ALLYLOXY)-4,5,6-TRIS(BENZYLOXY)-1,2-CYCLOHEXANEDIOL(CAS DataBase Reference)
• NIST Chemistry Reference: 3-(ALLYLOXY)-4,5,6-TRIS(BENZYLOXY)-1,2-CYCLOHEXANEDIOL(1214020-75-3)
• EPA Substance Registry System: 3-(ALLYLOXY)-4,5,6-TRIS(BENZYLOXY)-1,2-CYCLOHEXANEDIOL(1214020-75-3)

Safety Data

• Hazardous Substances Data: 1214020-75-3(Hazardous Substances Data)

Upstream product

• 1323371-32-9 6-O-allyl-3,4,5-tri-O-benzyl-1,2-O-{(+)-1,1,7-trimethylbicyclo[2.2.1]hept-6-ylidene}-L-myo-inositol 
• 131146-91-3 (+/-)-4-O-allyl-1,5,6-tri-O-benzyl-myo-inositol 
• 154372-19-7 C₃₆H₄₂O₆ 
• 1186371-24-3 C₃₃H₃₈O₆ 
• 1323371-30-7 6-O-allyl-3,4,5-tri-O-benzyl-1,2-O-{(+)-1,7,7-trimethyl[2,2,1]bicyclohepta-6-ylidene}-D-myo-inositol 
• 131147-11-0 (±)-2,3-O-isopropylidene-1,5,6-tri-O-benzyl-4-O-allyl-myo-inositol 
• 154459-93-5 1L-6-O-allyl-3-O-benzyl-1,2:4,5-di-O-cyclohexylidene-myo-inositol 
• 154459-83-3 1L-6-O-allyl-3-O-benzyl-1,2-O-cyclohexylidene-myo-inositol 
• 23393-20-6 D-1-O-benzyl-2,3:5,6-di-O-cyclohexylidene-myo-inositol 
• 100-39-0 benzyl bromide 
• 164904-89-6 6-O-allyl-3,4,5-tri-O-benzyl-1,2-O-cyclohexylidene-L-myo-inositol 
• 131147-11-0 (3aR,4S,5S,6R,7S,7aS)-4-Allyloxy-5,6,7-tris-benzyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxole 
• 51548-88-0 (+/-)-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 131146-87-7 (±)-1-O-allyl-4-O-benzyl-2,3:5,6-di-O-isopropylidene-myo-inositol 

Downstream Products

• 1323371-48-7 (3,4-di-O-benzyl-6-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->6)-1-O-p-methoxybenzyl-2,3,4,5-tetra-O-benzyl-L-myo-inositol 
• 1323371-47-6 (3,4-di-O-benzyl-6-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->6)-1-O-p-methoxybenzyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol 
• 131233-71-1 1D-4-O-allyl-1,5,6-tri-O-benzyl-myo-inositol 
• 154459-84-4 1L-6-O-allyl-3,4,5-tri-O-benzyl-1-O-(4-methoxybenzoyl)-myo-inositol 
• 154459-85-5 1L-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzoyl)-myo-inositol 
• 133076-44-5 (2-azido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl)-(1-6)-1-O-4-methoxybenzyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol 
• 380366-31-4 (3,4,6-tri-O-acetyl-2-azido-2-deoxy-α-D-glucopyranosyl)-(1->6)-2,3,4,5-tetra-O-benzyl-1-O-(4-methoxybenzyl)-D-myo-inositol 

Relevant articles and documents

Resolution of orthogonally protected myo-inositols with Novozym 435 providing an enantioconvergent pathway to Ac2PIM1

Orthogonally protected chiral myo-inositol derivatives are important intermediates for higher order myo-inositol-containing compounds. Here, the use of the immobilized enzyme Novozym 435 to efficiently catalyze the acetylation of the 5R configured enantio

Synthesis of non-hydrolysable mimics of glycosylphosphatidylinositol (GPI) anchors

Synthesis of first generation non-hydrolysable C-phosphonate GPI analogs, viz., 6-O-(2-amino-2-deoxy-α-d-glucopyranosyl)-d-myo-inositol-1-O-(sn-3,4- bis(palmitoyloxy)butyl-1-phosphonate) 23a and 6-O-(2-amino-2-deoxy-α-d- glucopyranosyl)-d-myo-inositol-1-O-(sn-2,3-bis(palmitoyloxy)propyl-1- phosphonate) 23b, is reported. The target compounds were synthesized by the coupling of α-pseudodisaccharide 21 with phosphonic acids 18a and 18b respectively in quantitative yield followed by de-protection. These synthetic C-phosphonate GPI-probes were resistant to phosphatidylinositol specific phospholipase C (PI-PLC) and also showed moderate inhibition of the enzyme activity. The Royal Society of Chemistry.

Stereoselective α-glycosylation of C(6)-hydroxyl myo-inositols via nickel catalysis - Application to the synthesis of GPI anchor pseudo-oligosaccharides

Glycosylphosphatidyl inositol (GPI) anchors play a key role in many eukaryotic biological pathways. Stereoselective synthesis of GPI anchor analogues have proven to be critical for probing the biosynthesis, structure, and biological properties of these co

Synthesis of new fluorescently labeled glycosylphosphatidylinositol (GPI) anchors

The borondipyrromethene (BODIPY) labeled new glycosylphosphatidylinositol (GPI) molecules were synthesized as cellular probes to study the chemical basis of microdomain organization of GPI-anchored proteins and cholesterol in plasma membrane. The synthesi

Efficient syntheses of chiral myo-inositol derivatives-key intermediates in glycosylphosphatidylinositol (GPI) syntheses

A facile and effective method was developed for large-scale syntheses of myo-inositol derivatives with the 1,2,6-O-positions differentiated from each other and from other positions as well. The syntheses started from methyl α-d-glucopyranoside, and the ke

Synthesis of phosphatidylinositol mannosides (PIMs)

Two strategies towards the synthesis of phosphatidylinositol mannosides (PIMs) were elaborated which permit selective access to the O-1-, O-2-, and the O-6 position of the myo-inositol residue. Starting materials are 1,2:5,6- and 1,2:4,5-di-O-cyclohexylid

First total synthesis of a GPI-anchored peptide

A GPI-anchored dipeptide of sperm CD52 antigen was prepared through a convergent synthesis. First, the dipeptide with its C-terminus free and the GPI with its nonreducing end phosphoeth-anolamine bearing a free amino group were synthesized separately. Then, the two building blocks were coupled with use of EDC/HOBt as the condensation reagent. Finally, the GPI-anchored peptide was deprotected to give the target molecule 1.

Convergent synthesis of an inner core GPI of sperm CD52

An inner core of the GPI anchor of sperm CD52 antigens was synthesized by a highly convergent process using specially modified inositol, glucosamine and phospholipid as key building blocks. This paper also presents a new and efficient procedure to prepare

An effective strategy for the synthesis of 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-chiro- and -D-myo-inositol 1-phosphate related to putative insulin mimetics

Two glycosylinositol phosphates related to putative insulin mimetics, 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-chiro-inositol 1-phosphate (1) and 6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-D-myo-inositol 1-phosphate (2), have been synthesized from selectively protected and enantiomerically pure D-chiro- and myo-inositol derivatives. The D-chiro-inositol unit was prepared in a multigram scale from D-glucose using the Ferrier's carbocyclization route, and it was transformed into the corresponding myo epimer by an oxidation-reduction sequence. The trichloroacetimidate method was applied efficiently for the key glycosylation of the inositol derivatives.

Parasite Glucoconjugates. Part 1. The Synthesis of Some Early and Related Intermediates in the Biosynthetic Pathway of Glycosyl-phosphatidylinositol Membrane Anchors

The enantio-pure 1D- and 1L-myo-inositol derivative 3D and 3L have been used to prepare sodium 1D-6-O-(2-amino-2-deoxy-α-D-glucopyranosyl)-myo-inositol sn-2,3-dipalmitoyloxypropyl phosphate 21 and a related 1,6-disubstituted 1L-myo-inositol 28, respective