132437-55-9

Upstream product

• 64681-28-3 D-1-O-allyl-3,4,5,6-tetra-O-benzyl-myo-inositol 
• 100-39-0 benzyl bromide 
• 132437-54-8 1-O-allyl-2,3,4,5-tetra-O-benzyl-D-myo-inositol 
• 202845-42-9 1-O-allyl-3,4,5-tri-O-benzyl-D-myo-inositol 
• 10583-42-3 (+/-)-1-O-allyl-3,4,5,6-tetrakis-O-benzyl myo-inositol 
• 135267-00-4 1-O-Allyl-2,3,4-tri-O-benzyl-D-chiro-inositol 
• 6691-27-6 (+/-)-cis-1,2-O-cyclohexylidene-3,4,5,6-tetrakis-O-benzyl myo-inositol 
• 6763-47-9 rac-1,2-O-cyclohexylidene-myo-inositol 
• 26276-99-3 rac-1,4,5,6-tetra-O-benzyl-myo-inositol 
• 100-44-7 benzyl chloride 
• 24558-77-8 3,4,5,6-tetra-O-benzyl inositol 
• 137793-90-9 (Z)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-gluco-hex-5-enopyranoside 
• 137793-96-5 (1R,2R,3S,4R,5S)-3,4,5-tribenzyloxy-2-hydroxy-6-oxocyclohexyl acetate 
• 137793-99-8 1-O-acetyl-3,4,5-tri-O-benzyl-D-myo-inositol 

Downstream Products

• 6195-45-5 (+)-2,3,4,5,6-pentakis-O-benzyl myo-inositol 
• 108235-14-9 D,L-2,3,4,5,6-penta-O-benzyl-myo-inositol 1-(methanesulfonate) 
• 134275-56-2 myo-inositol 1-(-3,4-di-palmitoyloxybutyl)-sulfonate 
• 134275-56-2 myo-inositol 1-(-3,4-di-palmitoyloxybutyl)-sulfonate 
• 134275-53-9 2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethanesulfonic acid (1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentakis-benzyloxy-cyclohexyl ester 
• 134275-53-9 2-(2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethanesulfonic acid (1S,2S,3R,4S,5S,6S)-2,3,4,5,6-pentakis-benzyloxy-cyclohexyl ester 
• 134275-54-0 3,4-Dihydroxy-butane-1-sulfonic acid (1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentakis-benzyloxy-cyclohexyl ester 
• 134275-54-0 3,4-Dihydroxy-butane-1-sulfonic acid (1S,2S,3R,4S,5S,6S)-2,3,4,5,6-pentakis-benzyloxy-cyclohexyl ester 
• 134275-55-1 Hexadecanoic acid 1-hexadecanoyloxymethyl-3-((1S,2R,3R,4S,5S,6R)-2,3,4,5,6-pentakis-benzyloxy-cyclohexyloxysulfonyl)-propyl ester 
• 158340-85-3 1,2,3,4,5-Penta-O-benzyl-D-chiro-inositol 
• 130277-51-9 DL,(6E)-1,2,3,4,5-Penta-O-benzyl-6-(methoxymethylidene)cyclohexane-1,2,4/3,5-pentol 
• 130277-51-9 DL,(6Z)-1,2,3,4,5-Penta-O-benzyl-6-(methoxymethylidene)cyclohexane-1,2,4/3,5-pentol 
• 130277-53-1 DL-3,4,5,6-Tetra-O-benzyl-3,5/4,6-tetrahydroxycyclohex-1-ene-1-methanol 
• 130277-53-1 DL-3,4,5,6-Tetra-O-benzyl-3,5,6/4-tetrahydroxycyclohex-1-ene-1-methanol 

Relevant academic research and scientific papers

Chemical synthesis of all phosphatidylinositol mannoside (PIM) glycans from Mycobacterium tuberculosis

The emergence of multidrug-resistant tuberculosis (TB) and problems with the BCG tuberculosis vaccine to protect humans against TB have prompted investigations into alternative approaches to combat this disease by exploring novel bacterial drug targets and vaccines. Phosphatidylinositol mannosides (PIMs) are biologically important glycoconjugates and represent common essential precursors of more complex mycobacterial cell wall glycolipids including lipomannan (LM), lipoarabinomannan (LAM), and mannan capped lipoarabinomannan (ManLAM). Synthetic PIMs constitute important biochemical tools to elucidate the biosynthesis of this class of molecules, to reveal PIM interactions with host cells, and to investigate the function of PIMs as potential antigens and/or adjuvants for vaccine development. Here, we report the efficient synthesis of all PIMs including phosphatidylinositol (Pl) and phosphatidylinositol mono- to hexa-mannoside (PIM1 to PIM6). Robust synthetic protocols were developed for utilizing bicyclic and tricyclic orthoesters as well as mannosyl phosphates as glycosylating agents. Each synthetic PIM was equipped with a thiol-linker for immobilization on surfaces and carrier proteins for biological and immunological studies. The synthetic PIMs were immobilized on microarray slides to elucidate differences in binding to the dendritic cell specific intercellular adhesion molecule-grabbing nonintegrin (DC-SIGN) receptor. Synthetic PIMs served as immune stimulators during immunization experiments in C57BL/6 mice when coupled to the model antigen keyholelimpet hemocyanin (KLH).

New fluorescent probes reveal that flippase-mediated flip-flop of phosphatidylinositol across the endoplasmic reticulum membrane does not depend on the stereochemistry of the lipid

Glycerophospholipid flip-flop across biogenic membranes such as the endoplasmic reticulum (ER) is a fundamental feature of membrane biogenesis. Flip-flop requires the activity of specific membrane proteins called flippases. These proteins have yet to be i

Syntheses of penta-O-benzyl-myo-inositols, O-β-L-arabinosyl-(1 → 2)sn-myo-inositol, O-α-D-galactosyl-(1 → 3)-sn-myo-inositol, and O-α-D-galactosyl-(1 → 6)-O-α-D-galactosyl-(1 → 3)-sn-myo-inositol

Two-step conversions of myo-inositol into (±)-2,3,4,5,6- and 1,3,4,5,6-penta-O-benzyl-myo-inositols are described. Starting from these monohydroxy derivatives of myo-inositol, O-β-L-arabinopyranosyl-(1→2)-sn-myo-inositol from Japanese green tea, Camellia sinensis, and O-α-D-galactopyranosyl-(1→3)-sn-myo-inositol (galactinol) as well as its homolog, O-α-D-galactopyranosyl-(1→6(II))-galactinol, were synthesized by way of the in situ activating glycosylation procedure.

Practical unequivocal synthesis of phosphatidyl-myo-inositols

The direct phosphatidylation of 1D-2,3,4,5,6-penta-O-benzyl-myo-inositol with sn-3-phosphatidic acid and subsequent hydrogenolytic debenzylation produces 1D-1-(sn-3-phosphatidyl)-myo-inositol in excellent yield (>90%) and unequivocal structural and stereo

Concerning the reactivities of the C-1, C-2 and C-6 hydroxy groups of myo-inositol

Regioselectivities in the reactions of the three contiguous free hydroxy groups at C-6, C-1, and C-2 of 3,4,5-tri-O-benzyl-D-myo-inositol have been examined. Stannylene activation permits selective alkylation and esterification at C-1; however, acyl migra

Ready routes to key myo-inositol component of GPIs employing microbial arene oxidation or Ferrier reaction

Microbial arene oxidation or Ferrier reaction of enol acetates provides versatile complementary routes that greatly facilitate preparation of inositol synthon(s) for GPI assembly.

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.

The absolute configuration of (+)-1,2,4,5,6-penta-O-benzyl-myo-inositol

The absolute configuration of (+)-1,2,4,5,6-penta-O-benzyl-myo-inositol is correlated with 1D-1,4,5,6-tetra-O-benzyl-myo-inositol and thus confirmed as 1D-1,2,4,5,6-penta-O-benzyl-myo-inositol.

Approaches to the synthesis of glycosyl phosphatidyl inositols. Enantioselective synthesis of optically active chiro- and myo-inositols

An efficient synthetic strategy to optically active conveniently substituted D-chiro (5) and D-myo-inositol (10) derivatives has been developed starting from methyl α-D-glucopyranoside. Compounds 5 and 10 constitute valuable intermediates for the preparation of glycosyl phosphatidyl inositols.

Synthesis of D- and L-myo-Inositol 1-phosphorothioate, Substrates for Inositol Monophosphatase

The D- and L- enantiomers of myo-inositol 1-phosphorothioate have been synthesized from 2,3,4,5,6-pentakis-O-benzyl myo-inositol in 6 steps, both compounds are substrates for inositol monophosphatase.D-glucopyranose 6-phosphorothioate did not serve as a s