136034-23-6

Basic information

• Product Name: β-D-Glucopyranosylphenylmethane
• Synonyms: β-D-Glucopyranosylphenylmethane
• CAS NO: 136034-23-6
• Molecular Weight: 254.283
• Mol File: 136034-23-6.mol

Chemical Properties

• CAS DataBase Reference: β-D-Glucopyranosylphenylmethane(CAS DataBase Reference)
• NIST Chemistry Reference: β-D-Glucopyranosylphenylmethane(136034-23-6)
• EPA Substance Registry System: β-D-Glucopyranosylphenylmethane(136034-23-6)

Safety Data

• Hazardous Substances Data: 136034-23-6(Hazardous Substances Data)

Upstream product

• 136034-18-9 (S)-[(4S,5R,6R)-3-((S)-Benzenesulfinyl)-4,5-bis-benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl]-phenyl-methanol 
• 136034-19-0 (2S,4S,4aS,6R,7R,8S,8aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2,4-diphenyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 136034-22-5 2,6-anhydro-3,4,5,7-tetra-O-benzyl-(1S)-C-phenyl-D-erythro-L-guloheptitol 
• 105938-05-4 (S)-((4R,5S,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-5,6-dihydro-4H-pyran-2-yl)-phenyl-methanol 
• 118916-46-4 (2R,3R,4S)-5-((S)-Benzenesulfinyl)-3,4-bis-benzyloxy-2-benzyloxymethyl-3,4-dihydro-2H-pyran 
• 100-52-7 benzaldehyde 
• 54423-54-0 2,3,4,6-Tetra-O-benzyl 1-O-p-nitrobenzoyl D-glucopyranoside 
• 100-44-7 benzyl chloride 
• 133697-34-4 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol 
• 13096-62-3 (3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one 
• 1589-82-8 phenylmagnesium bromide 
• 59531-24-7 2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 4196-35-4 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl bromide 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 

Downstream Products

• 727416-82-2 C₂₀H₂₁ClO₅ 
• 727416-83-3 C₂₀H₂₁ClO₅ 
• 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 
• 161909-26-8 (2,3,4,6-Tetra-O-acetyl-β-D-glucopyranosyl)-4-aminophenylmethane 
• 511274-76-3 Undec-10-enoic acid (2R,3R,4R,5S,6S)-6-benzyl-4,5-dimethoxy-2-undec-10-enoyloxymethyl-tetrahydro-pyran-3-yl ester 
• 511274-74-1 Pent-4-enoic acid (2R,3R,4R,5S,6S)-6-benzyl-4,5-dimethoxy-2-pent-4-enoyloxymethyl-tetrahydro-pyran-3-yl ester 
• 511274-43-4 (2R,3R,4S,5S,6S)-6-Benzyl-2-hydroxymethyl-4,5-dimethoxy-tetrahydro-pyran-3-ol 

Relevant articles and documents

Synthesis and screening of bicyclic carbohydrate-based compounds: A novel type of antivirals

A small library of bicyclic carbohydrate derivatives was synthesized and screened. A strong and selective activity against cytomegalovirus was found. Structure-activity relationship for this new type of antivirals is discussed.

A convergent ring-closing metathesis approach to carbohydrate-based macrolides with potential antibiotic activity

An efficient convergent approach has been developed for the construction of novel, non-natural, carbohydrate-based macrolides. The key step in the synthesis is the formation of the macrocyclic ring via a ring-closing metathesis reaction. The obtained macrolide analogues have been screened for biological activity against Gram-positive and Gram-negative bacteria, including resistant strains, yeasts, and molds.

Bicyclic carbohydrate compounds useful in the treatment of infections caused by herpesviridae

Bicyclic carbohydrates for the treatment of infections caused by herpseviridae, and in particular cytomegalovirus. The invention consists of the novel bicyclic carbohydrates the generic structure of which is: wherein R1 is either -Bn or -Ph; R2 and R3 are either -alkyl, -aryl, -allyl, or —H; R4 and R5 form a ring and are either —CH(Ph)- or —CH(aryl)- and X is either O, N or S.

Bicyclic carbohydrates as antiviral bioactives for the treatment of infections caused by the alphaherpesvirinae HSV-1 and HSV-2

Novel bicyclic carbohydrate compounds are effective for the prophylaxis and treatment of diseases caused by infections of the alphaherpesvirinae HSV-1 and HSV-2. The invention includes the compound wherein X1, X2, and X3 are selected from the group consisting of O, N, and S; wherein Y1 and Y2 are selected from the group consisting of O, N, and S; and wherein Z is selected from the group consisting of F, Cl, and Br, as well as analogs, prodrugs and pharmaceutically acceptable salts thereof, together with pharmaceutical compositions for the prophylaxis and treatment of diseases caused by infections of alphaherpesvirinae.

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.