136034-24-7

Upstream product

• 108-24-7 acetic anhydride 
• 136034-23-6 β-D-Glucopyranosylphenylmethane 
• 100-44-7 benzyl chloride 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 54423-54-0 2,3,4,6-Tetra-O-benzyl 1-O-p-nitrobenzoyl D-glucopyranoside 
• 6921-34-2 benzylmagnesium chloride 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 67773-43-7 2,3,4,6-tetra-O-benzyl-α/β-D-glucopyranosyl bromide 
• 155590-31-1 (2,3,4,6-Tetra-O-benzyl-β-D-glucopyranosyl)phenylmethane 
• 133697-34-4 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 4451-36-9 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl chloride 

Downstream Products

• 179119-49-4 (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)(4-nitrophenyl)methane 
• 1350930-36-7 (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)(2-nitrophenyl)methane 
• 6067-21-6 methyl 2,3,4,6-tetra-O-acetyl-D-gluconate 
• 158419-80-8 (2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-4-retinamidophenylmethane 
• 158419-85-3 (Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4-retinamidophenylmethane 
• 158419-84-2 (Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)-4-aminophenylmethane 
• 158419-81-9 (Methyl 2,3,4-tri-O-acetyl-β-D-glucopyranosyluronate)phenylmethane 
• 161909-26-8 (2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-4-aminophenylmethane 
• 136034-23-6 β-D-Glucopyranosylphenylmethane 

Relevant academic research and scientific papers

Photochemical conversion of the o-nitrobenzyl-C-glucoside to a sugar lactone

A new family of activated glycosidic compounds has been designed and synthesized: (2,3,4,6-tetra-O-acetyl-β-d-glucopyranosyl)-2- nitrophenylmethane (1). It is stable in conditions commonly used for synthesis, and it can be converted to a sugar lactone der

Suzuki cross-coupling of carbohydrates: Synthesis of β-arylmethyl-C-glycosides and aryl-scaffolded trisaccharide mimics

β-1-C-Arylmethylglycoside derivatives of D-glucose and D-mannose have been synthesized using a mild hydroboration/Suzuki cross-coupling sequence. The scope and limitations of this methodology as well as its extension to the construction of aryl scaffolded trisaccharide mimics is described.

REACTION OF GLYCOSYL HALIDES WITH BENZYL GRIGNARD REAGENTS: UNEXPECTED o-TOLYL ALKYLATION OF TETRA-O-ACETYLGLUCOPYRANOSYL BROMIDE AND DIRECT SYNTHESIS OF (β-GLYCOSYL)PHENYLMETHANES

The synthesis of (β-glycosyl)phenylmethanes by Grignard alkylation of glycosyl halides is investigated.Reaction of tetra-O-acetylglucopyranosyl bromide with benzylmagnesium chloride gave a good yield of a 3:1 mixture of 2-(β-D-glucopyranosyl)toluene and (β-glucosyl)phenylmethane.The requirement for an equatorial 2-acetoxy group and 6-acetoxymethyl group for the formation of the unexpected o-tolyl rearrangement product is explored by using xylosyl, mannosyl, and 2-deoxyglucosyl halides as substrates for the alkylation.Synthesis of (β-glucosyl)phenylmethane by alkylation of 2,3,4,6-tetra-O-benzylglucosyl bromide with benzylmagnesium chloride is also presented.

PREPARATION OF 4-RETINAMIDOPHENYL- AND 4-RETINAMIDOBENZYL-C-GLYCOSYL AND C-GLUCURONOSYL ANALOGUES OF THE GLUCURONIDE OF 4-HYDROXYPHENYLRETINAMIDE AS POTENTIAL STABLE CANCER CHEMOPREVENTIVE AGENTS

Glucuronide metabolites of retinoic acid and its analogues have been suggested to be active cancer chemopreventive analogues of the parent molecules.However, these metabolites are susceptible to β-glucuronidase and acid-catalyzed cleavage and it is not clear whether these carbohydrate conjugates must be hydrolyzed back to the parent molecule to show activity.Thus, the multistep syntheses of stable C-glycosyl and C-glucuronosyl analogues of the known glucuronide metabolite of the breast cancer chemopreventive agent 4-hydroxyphenylretinamide (4-HPR) are outlined.The chemical and enzymatic stability of these compounds has been evaluated relative to the glucuronide of 4-HPR.