66026-10-6

Basic information

• Product Name: Benzyl 2-Acetamido-2-deoxy-4,6-O-isopropylidene-a-D-glucopyranoside
• Synonyms: PhenylMethyl 2-(AcetylaMino)-2-deoxy-4,6-O-(1-Methylethylidene)-α-D-glucopyranoside;α-D-Glucopyranoside, phenylMethyl 2-(acetylaMino)-2-deoxy-4,6-O-(1-Methylethylidene)-;N-((4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide(WXG01684)
• CAS NO: 66026-10-6
• Molecular Formula: C₁₈H₂₅NO₆
• Molecular Weight: 351.397
• Product Categories: 13C & 2H Sugars;Carbohydrates & Derivatives
• Mol File: 66026-10-6.mol
• Article Data: 6

Chemical Properties

• Melting Point: 136-138°C
• Boiling Point: 567.57°C at 760 mmHg
• Flash Point: 297.056°C
• Appearance: /
• Density: 1.259g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.561
• Storage Temp.: -20°C Freezer
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 12.80±0.70(Predicted)
• CAS DataBase Reference: Benzyl 2-Acetamido-2-deoxy-4,6-O-isopropylidene-a-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Benzyl 2-Acetamido-2-deoxy-4,6-O-isopropylidene-a-D-glucopyranoside(66026-10-6)
• EPA Substance Registry System: Benzyl 2-Acetamido-2-deoxy-4,6-O-isopropylidene-a-D-glucopyranoside(66026-10-6)

Safety Data

• Hazardous Substances Data: 66026-10-6(Hazardous Substances Data)

Usage

Chemical Properties

White Crystalline Solid

InChI:InChI=1/C18H25NO6/c1-11(20)19-14-15(21)16-13(10-23-18(2,3)25-16)24-17(14)22-9-12-7-5-4-6-8-12/h4-8,13-17,21H,9-10H2,1-3H3,(H,19,20)/t13?,14-,15+,16+,17-/m0/s1

Upstream product

• 10036-64-3 N-acetyl-D-glucosamine 
• 67-64-1 acetone 
• 100-51-6 benzyl alcohol 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 3006-58-4 2-carbobenzyloxyamino-2-deoxy-D-glucopyranose 
• 3055-51-4 benzyl 2-deoxy-2-(N-acetylamino)-D-glucopyranoside 
• 77-76-9 2,2-dimethoxy-propane 
• 13343-62-9 benzyl 2-acetamido-2-deoxy-α-D-glucopyranoside 

Downstream Products

• 67398-54-3 benzyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside 
• 69323-67-7 (R)-2-(((4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanoic acid 
• 78604-09-8 2-(((4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)acetic acid 
• 62928-83-0 benzyl (R)-4-((S)-2-((R)-2-(((2S,3R,4R,5S,6R)-3-acetamido-2-(benzyloxy)-5-hydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-4-yl)oxy)propanamido)propanamido)-5-amino-5-oxopentanoate 
• 69323-69-9 benzyl (R)-4-((S)-2-((R)-2-(((4aR,6S,7R,8R,8aS)-7-acetamido-6-(benzyloxy)-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-8-yl)oxy)propanamido)propanamido)-5-amino-5-oxopentanoate 
• 128753-61-7 2-acetamido-2-deoxy-3-O-carbamoyl-4,6-di-O-acetyl-α-D-glucopyranos-1-yl (2'R')-2'-carbomethoxy-2'-(pentyloxy)-eth-1'-yl phenyl phosphate 
• 128753-60-6 Acetic acid (2R,3S,4R,5R,6R)-2-acetoxymethyl-5-acetylamino-4-carbamoyloxy-6-(diisopropylamino-phenoxy-phosphanyloxy)-tetrahydro-pyran-3-yl ester 
• 128753-54-8 benzyl 2-acetamido-2-deoxy-3-O-carbamoyl-4,6-di-O-acetyl-α-D-glucopyranoside 
• 128753-70-8 benzyl 2-acetamido-2-deoxy-3-O-carbamoyl-α-D-glucopyranoside 
• 120484-38-0 Benzyl 2-acetamido-4-O-(tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-6-O-benzoyl-2-deoxy-3-O-(methoxycarbonyl)methyl-α-D-glucopyranoside 
• 120484-37-9 N-<2-O--glycoloyl>-L-α-aminobutanoyl-D-isoglutamine benzyl ester 
• 120496-14-2 Benzyl 2-acetamido-4-O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-carboxymethyl-α-D-glucopyranoside 
• 127528-40-9 Benzyl 2-acetamido-4,6-di-O-benzoyl-2-deoxy-3-O-(methoxycarbonyl)methyl-α-D-glucopyranoside 
• 127528-43-2 Benzyl 2-acetamido-4-O-(2-amino-2-deoxy-β-D-glucopyranosyl)-2-deoxy-3-O-carboxymethyl-α-D-glucopyranoside 

Relevant articles and documents

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Porphyromonas gingivalis (P.g.)-induced TNF-α can be affected by muramyl dipeptide (MDP) in a biphasic concentration-dependent manner. We found that in P.g.-exposed macrophages, treatment with 10 μg/mL of MDP (MDP-low) up-regulated TNF-α by 29%, while 100

Synthesis of C(6)-carboxylate analogues of N-acetylmuramic acid

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AN ALTERNATIVE SYNTHESIS OF O-(2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYL)-(1-4)-N-ACETYLNORMURAMOYL-L-α-AMINOBUTANOYL-D-ISOGLUTAMINE

Silver triflate-promoted condensation of 3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl bromide (VIII) with benzyl 2-acetamido-6-O-benzoyl-2-deoxy-3-O-(methoxycarbonyl)-methyl-α-D-glucopyranoside (IV) afforded benzyl 2-acetamido-4-O-(3,4,6-tri-O-acetyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-6-O-benzoyl-2-deoxy-3-O-(methoxycarbonyl)methyl-α-D-glucopyranoside (IX) which, after deprotection, was converted into the acid XI.Condensation of acid XI with L-α-aminobutanoyl-D-isoglutamine benzyl ester and subsequent hydrogenolysis of the product XIII furnished compound XIV.Benzyl 2-acetamido-6-O-benzoyl-2-deoxy-3-O-(methoxycarbonyl)methyl-α-D-glucopyranoside (IV) was prepared by partial benzoylation of benzyl 2-acetamido-2-deoxy-3-O-(methoxycarbonyl)methyl-α-D-glucopyranoside (III) with benzoyl cyanide.