18929-63-0

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 2186-92-7 p-Anisaldehyde dimethyl acetal 
• 1515-81-7 1-methoxy-4-(methoxymethyl)benzene 

Downstream Products

• 94902-60-0 methyl 2,3-di-O-benzyl-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside 
• 299199-12-5 methyl 2-O-benzyl-4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside 
• 182760-09-4 methyl 2,3-bis-O-(4-methoxyphenyl)methyl-4,6-O-(4-methoxybenzylidene)-α-D-glucopyranoside 
• 130523-98-7 (2S,3S,4S,5R,6S)-4,5-Bis-benzyloxy-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-2-carbaldehyde 
• 90633-95-7 methyl 2,3-bis-O-benzyl-4-O-[(4-methoxyphenyl)methyl]-α-D-glucopyranoside 
• 167394-68-5 1-O-acetyl-3,4-bis-O-benzyl-5-O-[(4-methoxyphenyl)methyl]-D-myo-inositol 
• 161364-90-5 (2R,3R,4S,5R,6S)-2-acetoxy-3-hydroxy-4,5-bis-O-benzyl-6-O-[(4-methoxyphenyl)methyl]-cyclohexanone 
• 167394-67-4 Acetic acid (3S,4S,5R,6S)-4,5-bis-benzyloxy-6-methoxy-3-(4-methoxy-benzyloxy)-tetrahydro-pyran-(2Z)-ylidenemethyl ester 
• 209050-73-7 (1R,2S,3R,4R,5S,6S)-3,4-Bis-benzyloxy-2,6-bis-benzyloxymethoxy-5-(4-methoxy-benzyloxy)-cyclohexanol 
• 52526-75-7 methyl 2,3-di-O-methyl-4,6-O-p-methoxybenzylidene-α-D-glucopyranoside 

Relevant academic research and scientific papers

KINETIC ACETALIZATION FOR 1,2- AND 1,3-DIOL PROTECTION BY THE REACTION OF p-METHOXYPHENYLMETHYL METHYL ETHER WITH DDQ

When 1,2- and 1,3-diols were treated with p-methoxyphenylmethyl methyl ether (MPMME) in the presence of DDQ, the kinetically controlled oxidative acetalization occurred smoothly even in case of acid-labile compounds to give p-methoxybenzylidene acetals ra

Iron(III)-catalyzed prins cyclization towards the synthesis of trans-Fused bicyclic tetrahydropyrans

trans-Fused bicyclic tetrahydropyrans have been synthesized through an intramolecular Prins cyclization catalyzed by iron(III). The cyclization process is stereoselective, leading exclusively to an all-cis configuration in the newly generated ring. This u

Saccharide conjugates

The invention provides a series of novel Lipid A analogs that are structually simple, synthetically accessible, and capable of blocking the cellular receptor within the signal transduction pathway. The novel Lipid A analogs can include a monosaccharide co

Three Solvent-Free Catalytic Approaches to the Acetal Functionalization of Carbohydrates and Their Applicability to One-Pot Generation of Orthogonally Protected Building Blocks

Three alternative protocols were developed to carry out the selective installation of acetal groups on carbohydrates and polyols under mildly acidic, solvent-free conditions. One protocol is based on a diol/aldehyde condensation at room temperature, with an acetolysis process serving for the activation of the carbonyl component. A second approach is based on an orthoester-mediated activation of the carbonyl component at high temperature. The third protocol is instead entailing a transacetalation mechanism. Combination of these methods allows a wide set of acetal-protected building blocks to be accessed in short times under very simple experimental conditions working under air. The scope of the latter two approaches was also extended to unusual one-pot synthetic sequences leading to concomitant Fischer glycosidation/acetal protection of reducing sugars.

NOVEL GLUCOPYRANOSE DERIVATIVES, PREPARATION THEREOF, AND BIOLOGICAL USES THEREOF

The invention relates to a novel ester, the 3,5-di-tertiobutyl-4-hydroxybenzoate of 3,4,5-trihydroxy-6-methoxytetrahydropyran-2-yl methyl defined by the following formula (I). The invention also relates to the method for preparing the compound of formula

Synthesis and biological evaluation of novel lipid A antagonists

A mimetic of Lipid A with a β-N(OMe) glycosidic linkage, four linear C-14 hydrophobic chains and without phosphate groups has been prepared together with its β-O-linked analogue. Both these molecules were active in inhibiting the inflammatory action of Es

Directing-protecting groups for carbohydrates. Design, conformational study, synthesis and application to regioselective functionalization

A novel concept of regioselective transformation of secondary hydroxyl groups in carbohydrates is presented. First, the relative reactivity of the free hydroxyl groups of onoprotected d-glucose derivatives was assessed using acetylation as a model reactio

Synthetic studies on oligosaccharides composed of 5-thioglucopyranose units

Glycosylation reactions of 5-thioglucopyranosyl trichloroacetimidates bearing ethereal protective groups at the 2-O-position 14-15, and 37 proceed smoothly to give α-glycosides stereoselectively by using a catalytic amount of silyl triflate. This methodol

Synthesis of L-α-phosphatidyl-D-myo-inositoi 5-phosphate and L-α- phosphatidyl-D-myo-inositol 3,5-bisphosphate

Two new 5-phosphorylated phosphatidylinositols have been synthesized from methyl α-D-glucopyranoside as the chiral precursor. These new PtdInsP(n)s have been recently detected in mammalian cells.

Chiral cyclopentane-based mimics of D-myo-inositol 1,4,5-trisphosphate from D-glucose

Two routes from D-glucose to chiral, ring-contracted analogs of the second messenger D-myo-inositol 1,4,5-trisphosphate are described. Methyl α-D-glucopyranoside was converted by an improved procedure into methyl 4,6-O-(p-methoxybenzylidene)-α-D-glucopyranoside (6) and thence into methyl 2-O-benzyl-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hexodialdopyranoside (1,5) (14) in four steps. In the first ring-contraction method 14 was converted into methyl 2-O-benzyl-6,7-dideoxy-3,4-bis-O-(p-methoxybenzyl)-α-D-gluco-hept-6-e nopyranoside (1,5) (15), which on sequential treatment with Cp2Zr(n-Bu)2 followed by BF3·Et2O afforded a mixture of (1R,2S,3S,4R,5S)-3-(benzyloxy)-4-hydroxy-1,2-bis[(p-methoxybenzyl)oxy] -5-vinylcyclopentane (16) and its 4S,5R diastereoisomer 17. Removal of the p-methoxybenzyl groups of 16 and subsequent phosphorylation and deprotection afforded the first target compound, (1R,2R,3S,4R,5S)-3-hydroxy-1,2,4-tris(phosphonooxy)-5-vinylcyclopentan e (3). In the second route, intermediate 14 was subjected to SmI2-mediated ring contraction to give (1R,2S,3S,4R,5S)-3-(benzyloxy)-4-hydroxy-5-(hydroxymethyl)-1,2-bis[(p- methoxybenzyl)oxy]cyclopentane (20). Benzylation of 20 provided (1R,2S,3S,4R,5S)-3-(benzyloxy)-6-[(benzyloxy)methyl]-4-hydroxy-1,2-bis [(p-methoxybenzyl)oxy]cyclopentane (22) and (1R,2S,3S,4R,5S)-3,4-bis(benzyloxy)-5-(hydroxymethyl)-1,2-bis[(p-metho xybenzyl)oxy]cyclopentane (21), which were elaborated to the target trisphosphates (1R,2R,3S,4R,5S)-3-hydroxy-5-(hydroxymethyl)-1,2,4-tris(phosphonooxy)c yclopentane (4) and (1R,2S,3R,4R,5S)-1,2-dihydroxy-3,4-bis(phosphonooxy)-5-[(phosphonooxy) methyl]cyclopentane (5), respectively. Both 3 and 4 mobilized intracellular Ca2+, but 4 was only a few fold less potent than D-myo-inositol 1,4,5-trisphosphate, demonstrating that effective mimics can be designed that do not bear a six-membered ring.