38416-56-7

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Chemical Properties

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InChI:InChI=1/C36H39NO6/c1-27(38)37-33-35(41-24-30-18-10-4-11-19-30)34(40-23-29-16-8-3-9-17-29)32(26-39-22-28-14-6-2-7-15-28)43-36(33)42-25-31-20-12-5-13-21-31/h2-21,32-36H,22-26H2,1H3,(H,37,38)/t32?,33-,34+,35+,36-/m0/s1

Upstream product

• 14146-27-1 benzyl 3-O-benzyl-2-acetamido-2-deoxy-α-D-glucopyranoside 
• 100-44-7 benzyl chloride 
• 7512-17-6 N-Acetyl-D-glucosamine 
• 108-24-7 acetic anhydride 
• 100-39-0 benzyl bromide 
• 4171-73-7 2-acetamido-1-O-acetyl-2-deoxy-3,4,6-tri-O-benzyl-α-D-glucopyranose 
• 100-51-6 benzyl alcohol 
• 67398-54-3 benzyl 2-acetamido-3-O-benzyl-2-deoxy-4,6-O-isopropylidene-α-D-glucopyranoside 
• 66026-10-6 N-((4aR,6S,7R,8R,8aS)-6-(benzyloxy)-8-hydroxy-2,2-dimethylhexahydropyrano[3,2-d][1,3]dioxin-7-yl)acetamide 
• 13343-63-0 benzyl 4,6-O-benzylidene-2-acetylamino-2-deoxy-α-D-glucopyranoside 
• 14146-26-0 benzyl 2-acetamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-α-D-glucopyranoside 

Relevant academic research and scientific papers

Formation of 2-acetamido-2-deoxy-d-glucopyranosidic linkages via glycosidation using a combination of two lewis acids

A mixed activation system composed of ytterbium(III) triflate and a catalytic boron trifluoride diethyl etherate complex efficiently promotes the glycosylation of various alcohol acceptors using 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D-glucopyranosyl ac

Order of reactivity of OH/NH groups of glucosamine hydrochloride and N -Acetyl glucosamine toward benzylation using NaH/BnBr in DMF

The order of reactivity of OH and NH groups of glucosamine hydrochloride (GlcNH2HCl) and N-acetyl glucosamine (GlcNAc) toward benzylation with NaH/BnBr in DMF was investigated. For GlcNH2.HCl, benzyl groups were introduced in the order of N-Bn > N-Bn2 > 1-O-Bn > 6-O-Bn > 4-O-Bn > 3-O-Bn; for GlcNAc, benzyl groups were introduced in the order of 1-O-Bn > 6-O-Bn > 4-O-Bn > 3-O-Bn > N-Bn. A range of partially benzylated 2-N,N′-dibenzyl glucopyranosides and GlcNAc derivatives were obtained in a single step. Taylor & Francis Group, LLC.

Formation of 1,2-CIS-α-aryl-glycosidic linkages directly from 2-acetamido-2-deoxy-D-glucopyranosyl acetate by the mixed activating system using ytterbium(III) triflate and catalytic boron trifluoride diethyl etherate complex

We found that a mixed activating system using ytterbium(III) triflate and a catalytic boron trifluoride diethyl etherate complex efficiently promoted glycosidation of the 2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-α-D- glucopyranosyl acetate in dichloromethane at room temperature to afford 2-acetamido-2-deoxy-Dglucopyranosides in good yields along with the formation of a considerable amount of α-isomers. Glycosylations of the aryl alcohols as the acceptors stereoselectively afforded aryl α-glycosides without producing any β-isomers.

Preparation of O-Hydroxyethyl and O-Hydroxypropyl Derivatives of D-Glucose and 2-Acetamido-2-deoxy-D-glucose for Studies of Modified Hyaluronic Acid

Some hydroxyethyl and hydroxypropyl derivatives of D-glucose and of 2-acetamido-2-deoxy-D-glucose have been sunthesized for use as reference substances for structural studies of hydroxyethylated and hydroxypropylated hyaluronic acid.Hydroxyethyl and hydroxypropyl substituents were introduced in the 2-O- or 3-O-position of D-glucose and in the 4-O- or 6-O-positions of 2-acetamido-2-deoxy-D-glucose by reaction of suitably protected sugars with either ethylene oxide or propylene oxide.For hydroxyethyl derivatives yields varied between 21 and 74percent and with a substantial portion of the doubly alkylated compounds.For hydroxypropyl derivatives yields varied between 15 and 80percent.Only trace amounts of the doubly alkylated compounds were found.The proportions of the respective derivatives were estimated using GLC-MS.All products were characterized by 1H and 13C NMR spectroscopy.

Synthesis of carbohydrate analogs (positional, configurational, and optical) of n-acetylmuramoyl-L-alanyl-D-isoglutamine, and their immunoadjuvant activities.

2-Acetamido-2-deoxy-4- and -6-O-(D-2-propanoyl-L-alanyl-D-isoglutamine)-D-glucopyranose, 2-acetamido-2-deoxy-3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine)-D-allopyranose, -D-gulopyranose, -D-galactopyranose, -D-mannopyranose, and -L-idopyranose, and 3-O-(D-2-propanoyl-L-alanyl-D-isoglutamine)-D- and -L-glucopyranose were synthesized, in order to clarify the structural requirements for the immunoadjuvant activity of the carbohydrate moiety in N-acetylmuramoyl-L-alanyl-D-isoglutamine. Immunoadjuvant activity of the N-acetylmuramoyl-dipeptide analogs was examined in guinea-pigs.