119943-93-0

Basic information

• Product Name: 1-O-(tert-butyldiphenylsilyl)-2,3:5,6-di-O-isopropylidene-D-myo-inositol
• Synonyms: 1-O-(tert-butyldiphenylsilyl)-2,3:5,6-di-O-isopropylidene-D-myo-inositol
• CAS NO: 119943-93-0
• Molecular Weight: 498.692
• Mol File: 119943-93-0.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: 1-O-(tert-butyldiphenylsilyl)-2,3:5,6-di-O-isopropylidene-D-myo-inositol(CAS DataBase Reference)
• NIST Chemistry Reference: 1-O-(tert-butyldiphenylsilyl)-2,3:5,6-di-O-isopropylidene-D-myo-inositol(119943-93-0)
• EPA Substance Registry System: 1-O-(tert-butyldiphenylsilyl)-2,3:5,6-di-O-isopropylidene-D-myo-inositol(119943-93-0)

Safety Data

• Hazardous Substances Data: 119943-93-0(Hazardous Substances Data)

Upstream product

• 51548-88-0 (+/-)-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 58479-61-1 tert-butylchlorodiphenylsilane 
• 127940-26-5 (R)-Pyrrolidine-1,2-dicarboxylic acid 2-[(3aS,4R,4aR,7aR,8R,8aR)-8-(tert-butyl-diphenyl-silanyloxy)-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yl] ester 1-(2,2,2-trichloro-ethyl) ester 
• 128110-25-8 (L)-1,2:4,5-di-O-isopropylidene-myo-inositol 
• 119874-35-0 1⁽³⁾-O-(tert-butyldiphenylsilyl)-2,3⁽¹⁾:5,6⁽⁴⁾-di-O-isopropylidene-D-myo-inositol 
• 1219455-51-2 8-(tert-Butyl-diphenyl-silanyloxy)-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-ol 
• 119874-36-1 1-O-(tert-butyldiphenylsilyl)-4-O-camphanyl-2,3:5,6-di-O-isopropylidene-D-myo-inositol 

Downstream Products

• 124648-22-2 3-O-(tert-butyldiphenylsilyl)-1,2:4,5-di-O-isopropylidene-D-myo-inositol 
• 119874-40-7 2,3:5,6-di-O-isopropylidene-4-O-(4-methoxytetrahydropyran-4-yl)-D-myo-inositol 1-(1,2-di-O-hexadecanoyl-sn-glycer-3-yl phenyl phosphate) 
• 119874-37-2 1-O-(tert-butyldiphenylsilyl)-4-O-(4-methoxytetrahydropyran-4-yl)-2,3:5,6-di-O-isopropylidene-D-myo-inositol 
• 119943-95-2 1D-myo-inositol-1-(1',2'-di-O-hexadecanoyl-sn-glycer-3'-yl sodium phosphate) 
• 119874-38-3 4-O-(4-methoxytetrahydropyran-4-yl)-2,3:5,6-di-O-isopropylidene-D-myo-inositol 
• 119874-40-7 2,3:5,6-di-O-isopropylidene-4-O-(4-methoxytetrahydropyran-4-yl)-D-myo-inositol 1-(2,3-di-O-hexadecanoyl-sn-glycer-1-yl phenyl phosphate) 
• 124649-44-1 6-O-(4-methoxytetrahydropyran-4-yl)-1,2:4,5-di-O-isopropylidene-D-myo-inositol 
• 127940-24-3 Hexadecanoic acid (R)-1-hexadecanoyloxymethyl-2-[((3aS,4R,4aR,7aS,8R,8aS)-8-hydroxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yloxy)-phenoxy-phosphoryloxy]-ethyl ester 
• 127940-24-3 Hexadecanoic acid (R)-1-hexadecanoyloxymethyl-2-[((3aR,4S,4aR,7aS,8S,8aR)-8-hydroxy-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yloxy)-phenoxy-phosphoryloxy]-ethyl ester 
• 127940-25-4 Hexadecanoic acid (R)-2-{[(3aR,4R,4aR,7aS,8R,8aR)-8-(diphenoxy-phosphoryloxy)-2,2,6,6-tetramethyl-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-yloxy]-phenoxy-phosphoryloxy}-1-hexadecanoyloxymethyl-ethyl ester 
• 57606-15-2 dipalmitoyl-L-α-phosphatidyl-D-myo-inositol 4-phosphate 
• 127940-28-7 2,3:5,6-di-O-isopropylidene-D-myo-inositol-1-O-mesitylenesulphonate 
• 161003-28-7 (3aR,4S,4aR,7aS,8S,8aR)-2,2,6,6-Tetramethyl-8-(tetrahydro-pyran-2-yloxy)-hexahydro-benzo[1,2-d;4,5-d']bis[1,3]dioxol-4-ol 

Relevant articles and documents

Synthesis and Cellular Labeling of Multifunctional Phosphatidylinositol Bis- and Trisphosphate Derivatives

We synthesized the first multifunctionalized phosphoinositide polyphosphate derivatives featuring a photo-removable protecting group (“cage”), a photo-crosslinkable diazirine group, and a terminal alkyne group useful for click chemistry. We demonstrate that the lipid derivatives readily enter cells. After photo-crosslinking, cell fixation and fluorescent tagging via click chemistry, we determined the intracellular location of the lipid derivatives before and after uncaging of the lipids. We find that there is rapid trafficking of PI(3,4)P2 and PI(3,4,5)P3 derivatives to the plasma membrane, opening the intriguing possibility that there is active transport of these lipids involved. We employed the photo-crosslinking and click chemistry functions to analyze the proteome of PI(3,4,5)P3-binding proteins. From the latter, we validated by RNAi that the putative lipid binding proteins ATP11A and MPP6 are involved in the transport of PI(3,4,5)P3 to the plasma membrane.

Inhibition of human erythrocyte membrane phosphatidylinositol 4-kinase by phospholipid analogues

Analogues of phosphatidylinositol (PtdIns, 1) have been synthesized to investigate the structural requirements for inhibition of a PtdIns 4-kinase obtained from human erythrocyte membranes. While the presence of either D-1 or D-3 stereochemistry in the inositol moiety greatly influences the degree of inhibition produced by PtdIns analogues, the stereochemistry of the glycerol moiety is of little consequence. Neither structural feature however, makes a significant contribution to binding affinity. Competitive inhibitory activity was found to be retained (or even enhanced) in substantially simpler analogues consisting of 1 or 2 hydrocarbon chains attached to a charged phosphate head group, such as in the phosphatidic acids, 24 and 26. The observation that the phosphatidylinositol 4-phosphate (PtdIns 4P) and phosphatidic acid analogues (eg, 16 or 17, and 26 respectively) inhibit PtdIns 4-kinase may suggest that such species have a regulatory role in PtdIns turnover.

IMPROVED SYNThESES OF INOSITOL PHOSPHOLIPID ANALOGUES

Short and convenient syntheses of PtdIns 4P and PtdIns analogues based on selective phosphorylation of (+)-2,3:5,6-di-O-isopropylidine-myo-inositol are presented.