169822-03-1

Basic information

• Product Name: allyl 2,6-di-O-benzyl-α-D-glucopyranoside
• Synonyms: allyl 2,6-di-O-benzyl-α-D-glucopyranoside
• CAS NO: 169822-03-1
• Molecular Weight: 400.472
• Mol File: 169822-03-1.mol

Chemical Properties

• CAS DataBase Reference: allyl 2,6-di-O-benzyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: allyl 2,6-di-O-benzyl-α-D-glucopyranoside(169822-03-1)
• EPA Substance Registry System: allyl 2,6-di-O-benzyl-α-D-glucopyranoside(169822-03-1)

Safety Data

• Hazardous Substances Data: 169822-03-1(Hazardous Substances Data)

Upstream product

• 169822-00-8 allyl 2,6-di-O-benzyl-3,4-O-isopropylidene-α-D-glucopyranoside 
• 178319-02-3 allyl 2,6-di-O-benzyl-3-O-p-methoxybenzyl-α-D-galactopyranoside 
• 178319-10-3 Benzoic acid (2R,3R,4S,5R,6S)-6-allyloxy-5-benzyloxy-2-benzyloxymethyl-4-(4-methoxy-benzyloxy)-tetrahydro-pyran-3-yl ester 
• 178319-04-5 allyl 2,6-di-O-benzyl-3-O-p-methoxybenzyl-4-O-methylsulfonyl-α-D-galactopyranoside 
• 37111-91-4 allyl 2,6-di-O-benzyl-α-D-galactopyranoside 
• 2280-44-6 D-Glucose 
• 314252-93-2 allyl 2,6-di-trimethylacetyl-3,4-O-isopropylidene-α-D-glucopyranoside 
• 314252-91-0 allyl 2,6-di-O-trimethylacetyl-α-D-glucopyranoside 
• 7464-56-4 1-O-allyl-α-D-glucopyranoside 
• 169822-02-0 allyl 3,4-O-isopropylidene-α-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 178319-05-6 allyl 2,6-di-O-benzyl-3-O-p-methoxybenzyl-α-D-glucopyranoside 

Downstream Products

• 314252-98-7 2,6-di-O-benzyl-3,4-di-O-(p-methoxybenzyl)-α-D-glucono-1,5-lactone 
• 314253-00-4 2,6-anhydro-3,7-di-O-benzyl-4,5-di-O-(p-methoxybenzyl)-1-deoxy-D-glucohept-1-enitol 
• 1357154-05-2 allyl 2,6-di-O-benzyl-3,4-bis-O-(dibenzyloxyphosphoryl)-α-D-glucopyranoside 
• 139684-64-3 (Z)-prop-1'-enyl 2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 6564-72-3 2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 169822-05-3 2-dibenzyloxyphosphoryloxyethyl 2,6-di-O-benzyl-3,4-bis-O-(dibenzyloxyphosphoryl)-α-D-glucopyranoside 
• 169822-04-2 (2-hydroxyethyl) 2,6-di-O-benzyl-α-D-glucopyranoside 
• 308290-86-0 2'',5',6''-tri-O-benzyl-2',3'',4''-tris(dibenzyloxyphosphoryl)-3'-O-α-D-glucopyranosyl-1-β-D-ribofuranosidoimidazole 
• 264230-07-1 2',3'',4''-tri-O-acetyl-2'',5',6''-tri-O-benzyl-3'-O-α-D-glucopyranosyl-9-β-D-ribofuranosidopurine 
• 403731-46-4 2'-O-acetyl-5'-O-benzyl-3'-O-(3,4-di-O-acetyl-2,6-di-O-benzyl-α-D-glucopyranosyl)uridine 

Relevant articles and documents

Design, Synthesis, and Insecticidal Activities of Novel Pyranoside Derivatives Targeting at Potential Second Calcium Channel IP3Receptor

In order to search for potent and environmental friendly insecticides with new modes of action, a series of pyranoside derivatives mimicking D-myo-inositol 1,4,5-trisphosphate (IP3) were designed and synthesized according to the bioisosteric approach. The biological assay indicated that most of the new compounds showed moderate to good insecticidal activities against oriental armyworm (Mythimna separata) and diamondback moth (Plutella xylostella). Especially, compound 5g displayed 80% larvicidal activity against oriental armyworm at 50 mg/L. Meanwhile, 5a showed 100% and 70% larvicidal activities against diamondback moth at 50 and 25 mg/L, respectively. To further explore the mode of action, calcium imaging technique was applied to study the effects of 5a, 5g, and 5i on the intracellular calcium ion concentration ([Ca2+]i) in central neurons isolated from Spodoptera exigua. The results indicated that the tested compounds released stored calcium ions from endoplasmic reticulum.

C-Glycoside based mimics of D-myo-inositol 1,4,5-trisphosphate

Epimeric C-glycoside based polyphosphates, α- and β-D-glucopyranosylmethanol 3,4,1'-trisphosphates (8 and 9) were prepared from D-glucose. The key intermediate, allyl 2,6-di-O-benzyl-α-D-glucopyranoside, was prepared in five steps (67% yield) from allyl α-D-glucopyranoside without the need for chromatography. Compounds 8 and 9 were shown to be full agonists at the Ins(1,4,5)P3 receptors of permeabilised hepatocytes, but with markedly different potencies. Such C-glycoside analogues are worthy of further development as Ins(1,4,5)P3 receptor ligands. (C) 2000 Elsevier Science Ltd.

A Ca2+-mobilising carbohydrate-based polyphosphate: Synthesis of 2- hydroxyethyl α-D-glucopyranoside 2',3,4-trisphosphate

Two routes to a glucose-based mimic of the second messenger 1D-myo- inositol 1,4,5-trisphosphate related to adenophostin A are described. Fischer glycosidation of D-glucose with allyl alcohol in the presence of a strong cation-exchange resin gave a 7:3 α:β-anomeric mixture of allyl glucopyranosides (5ab) from which the pure α anomer 5a was isolated by crystallisation. Treatment of 5ab with 1.05 equiv of dibutyltin oxide followed by 2.1 equiv of benzoyl chloride gave allyl 2,6-di-O-benzoyl-α-D- glucopyranoside, which was converted in 3 steps into allyl 2,6-di-O-benzyl- 3,4-O-isopropylidene-α-D-glucopyranoside (4). Alternatively, treatment of 5a with 2.5 equiv of dibutyltin oxide followed by benzyl bromide gave allyl 2,6-di-O-benzyl-α-D-glucopyranoside (9) which was also converted into 4. Compound 4 was elaborated to the phosphorylation precursor 2-hydroxyethyl 2,6-di-O-benzyl-α-D-glucopyranoside (12) in a convenient one-pot reaction, and 12 was phosphorylated and deblocked to afford 2-hydroxyethyl α-D- glucopyranoside 2',3.4-trisphosphate. The 2,6-di-O-benzyl derivative 9 was converted in high yield into 2,6-di-O-benzyl-3,4-di-O-(p-methoxybenzyl)-D- glucopyranose, a useful intermediate for the synthesis of adenophostin A and related compounds.

The allyl group for protection in carbohydrate chemistry. XXXI conversion of allyl 2,6-di-o-benzyl-α-d-galactopyranoside into allyl 2,6-di-o-benzyl-α-d-glucopyranoside and 2,6-di-o-benzyl-d-glucopyranose

Allyl 2,6-di-O-benzyl-α-D-galactopyranoside was converted by tin-mediated alkylation into the 3-O-p-methoxybenzyl ether which gave the 4-0-mesyl derivative. Sodium benzoate in refluxing N,N-dimethylformamide converted the last compound into allyl 4-O-benz

(2-hydroxyethyl)-α-D-glucopyranoside-2',3,4-trisphosphate: Synthesis of a second messenger mimic related to adenophostin A

A concise synthetic route from D-glucose to a chiral, biologically active, phosphorylated analogue of the highly potent Ca2+-mobilising agonist adenophostin A has been developed, involving a regioselective dibenzylation of allyl α-D-glucopyranoside and a one-pot Lemieux-type allyl oxidation with subsequent reduction and neighbouring deketalisation, to provide the key intermediate for phosphorylation.