65730-02-1

Basic information

• Product Name: 2-Propenyl 2-(Acetylamino)-2-deoxy-3,6-bis-O-(phenylmethyl)--D-glucopyranoside
• Synonyms: 2-Propenyl 2-(Acetylamino)-2-deoxy-3,6-bis-O-(phenylmethyl)--D-glucopyranoside;Allyl 2-(Acetylamino)-2-deoxy-3,6-bis-O-(phenylmethyl)--D-glucopyranoside;Allyl 2-(Acetylamino)-2-deoxy-3,6-bis-O-benzyl--D-glucopyranoside;Allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-b-D-glucopyranoside;Allyl 2-(Acetylamino)-2-deoxy-3,6-bis-O-benzyl-2-D-glucopyranoside
• CAS NO: 65730-02-1
• Molecular Formula: C₂₅H₃₁NO₆
• Molecular Weight: 441.51674
• Product Categories: Carbohydrates & Derivatives
• Mol File: 65730-02-1.mol

Chemical Properties

• Appearance: /
• Solubility: Methanol
• CAS DataBase Reference: 2-Propenyl 2-(Acetylamino)-2-deoxy-3,6-bis-O-(phenylmethyl)--D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Propenyl 2-(Acetylamino)-2-deoxy-3,6-bis-O-(phenylmethyl)--D-glucopyranoside(65730-02-1)
• EPA Substance Registry System: 2-Propenyl 2-(Acetylamino)-2-deoxy-3,6-bis-O-(phenylmethyl)--D-glucopyranoside(65730-02-1)

Safety Data

• Hazardous Substances Data: 65730-02-1(Hazardous Substances Data)

Usage

Chemical Properties

White Solid

Upstream product

• 65947-38-8 N-((4aR,6R,7R,8R,8aS)-6-Allyloxy-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl)-acetamide 
• 74352-48-0 allyl 2-acetamido-3-O-benzyl-2-deoxy-6-O-tosyl-β-D-glucopyranoside 
• 20194-18-7 sodium phenyl-methanolate 
• 74948-67-7 allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2-tetrahydropyranyl)-β-D-glucopyranoside 
• 275367-39-0 allyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-β-D-xylohexopyranosid-4-ulose 
• 70834-40-1 allyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-β-D-glucopyranoside 
• 74948-66-6 allyl 2-acetamido-3,6-di-O-benzoyl-2-deoxy-4-O-(2-tetrahydropyranyl)-β-D-glucopyranoside 
• 74653-17-1 allyl 2-acetamido-2-deoxy-4-O-(tetrahydropyran-2-yl)-β-D-glucopyranoside 
• 100-39-0 benzyl bromide 
• 28297-52-1 2-acetamido-4,6-O-benzylidene-2-deoxy-D-glucopyranose 
• 508194-14-7 allyl 2-acetamido-3-O-acetyl-(R)-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside 
• 3006-60-8 2-acetamido-3,4,6-tri-O-acetyl-D-glucopyranosyl acetate 
• 63064-48-2 allyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranoside 
• 54400-75-8 allyl 2-acetamido-2-deoxy-β-D-glucopyranoside 

Downstream Products

• 85386-50-1 allyl O-<2-O-benzoyl-3,6-di-O-benzyl-4-O-(tetrahydropyran-2-yl)-β-D-galactopyranosyl>-(1->4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 65730-05-4 1-propenyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 65371-99-5 Acetic acid (2R,3S,4R,5R,6R)-5-acetylamino-4-benzyloxy-2-benzyloxymethyl-6-[((E)-propenyl)oxy]-tetrahydro-pyran-3-yl ester 
• 78139-20-5 allyl 2-acetamido-4-O-(2-acetamido-4-O-acetyl-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 128693-83-4 allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 4-(diphenyl phosphate) 
• 85395-74-0 allyl 2-acetamido-3,6-di-O-benzyl-4-O-p-bromophenylsulfonyl-2-deoxy-β-D-glucopyranoside 
• 88524-50-9 N-[(2R,3R,4R,5S,6R)-2-Allyloxy-4-benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3-yl]-acetamide 
• 161545-34-2 allyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-trichloroacetamido-β-D-glucopyranosyl)-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 275367-39-0 allyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-β-D-xylohexopyranosid-4-ulose 
• 275367-43-6 allyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-4-O-(fluorosulfonylbenzoyl)-β-D-glucopyranoside 
• 65730-04-3 allyl 2-acetamido-2-deoxy-3,6-di-O-benzyl-4-O-acetyl-β-D-glucopyranoside 
• 147314-92-9 allyl O-(2-acetamido-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1<*>4)-2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside 
• 88509-75-5 allyl 2-acetamido-3,6-di-O-benzyl-4-O-(4,6-O-benzilidene-β-D-galactopyranosyl)-2-deoxy-glucopyranoside 
• 88509-74-4 allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-β-D-glucopyranoside 

Relevant articles and documents

Affinity labelling at the 4-hydroxyl group of N- acetylglucosamine and N-acetylgalactosamine

Derivatives of N-acetylgalactosamine and N-acetylglucosamine in which the 4-OH group could be selectively labelled have been prepared from a common precursor.

1,3,4,6-Tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranose as a glycosyl donor in syntheses of oligosaccharides

1,3,4,6-Tetra-O-acetyl-2-chloroacetamido-2-deoxy-β-D-glucopyranose was tested as a glycosyl donor for oligosaccharide synthesis via ferric chloride-catalyzed coupling reaction.Glycosyl acceptors tried (6 in all) were O-benzyl-protected D-galactosides having free OH groups at positions 3 and 4, respectively, and similarly protected glycosides of D-glucose and 2-acetamido-2-deoxy-D-glucose unsubstituted on O-4.Existing syntheses of all the acceptors were improved, in four instances by exploitation of Garegg and Hultberg's cyanoborohydride procedure for the conversion 4,6-O-benzylidene -> 6-O-benzyl .Good to excellent yields of β-linked disaccharides were obtained from the galactoside and glucoside acceptors, but with allyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside, stereoselectivity was lost (α:β-ratio 1:2).Allyl and benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosides gave, respectively, the allyl and benzyl β-glycosides of the donor as major products.A mechanism is proposed for this transglycosidation reaction.The N-chloroacetyl groups in the disaccharide products were readily converted into N-acetyl by reduction with zinc-acetic acid.

O-BENZYLATED OXAZOLINE DERIVATIVES OF 2-ACETAMIDO-2-DEOXY-D-GLUCOPYRANOSE FROM 1-PROPENYL GLYCOSIDES. SYNTHESIS OF THE PROPENYL GLYCOSIDES AND THEIR DIRECT CYCLIZATION

1-Propenyl 2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-α- and -β-D-glucopyranosides (3α, 3β) were obtained by the successive isomerization and acetylation of the known allyl glycosides 1α and 1β.The allyl glycosides were also converted, via their benzylidene 4