139195-28-1

Basic information

• Product Name: 2-C-(2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosyl) ethyne
• Synonyms: 2-C-(2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosyl) ethyne;2,6-Anhydro-7,8-dideoxy-1,3,4,5-tetrakis-O-(phenylmethyl)-D-glycero-L-gulo-oct-7-ynitol
• CAS NO: 139195-28-1
• Molecular Formula: C₃₆H₃₆O₅
• Molecular Weight: 548.66804
• Mol File: 139195-28-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 2-C-(2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosyl) ethyne(CAS DataBase Reference)
• NIST Chemistry Reference: 2-C-(2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosyl) ethyne(139195-28-1)
• EPA Substance Registry System: 2-C-(2,3,4,6-Tetra-O-benzyl-a-D-glucopyranosyl) ethyne(139195-28-1)

Safety Data

• Hazardous Substances Data: 139195-28-1(Hazardous Substances Data)

Upstream product

• 56822-49-2 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranoside 
• 79258-16-5 2,6-anhydro-1,3,4,5-tetra-O-benzyl-D-glycero-L-gulo-heptitol 
• 113019-43-5 2,6-Anhydro-3,4,5,7-tetra-O-benzyl-aldehydo-D-glycero-D-ido-heptopyranose 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 80300-30-7 1-O-acetyl-2,3,4,6-tetra-O-benzyl-D-glucopyranose 
• 56822-48-1 (2S,3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl acetate 
• 93267-04-0 N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester 
• 139195-57-6 2-iodoethenyl-2,3,4,6-tetra-O-benzyl-α-D-glucopyranoside 
• 141100-79-0 trimethyl-[2-[(2R,3S,4R,5R,6R)-3,4,5-tribenzyloxy-6-(benzyloxymethyl)tetrahydropyran-2-yl]ethynyl]silane 
• 81353-38-0 (trimethylsilylethynyl)tributyltin 
• 139195-27-0 (2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-(2,2-dibromo-vinyl)-tetrahydro-pyran 

Downstream Products

• 849359-26-8 2-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1-(p-toluenesulfonyl)indole 
• 849359-23-5 1-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-2-o-(p-toluenesulfoamidyl)phenylethyne 
• 1131376-40-3 (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)but-1-yne 
• 1384948-18-8 3-(2,3,4-tri-O-acetyl-β-L-fucopyranosyl)-2-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1H-indole 
• 1616112-12-9 (2R,3S,4R,5R,6R)-2-(hydroxymethyl)-6-[2-[4-[2-[(2R,3S,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]ethynyl]phenyl]ethynyl]tetrahydropyran-3,4,5-triol 
• 1620081-09-5 C₆₅H₆₈N₄O₈ 
• 139195-33-8 (Z)-(3S,4R,5R,6S)-4,5,6-Tris-benzyloxy-7-(tert-butyl-diphenyl-silanyloxy)-1-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hept-1-en-3-ol 
• 139195-33-8 (Z)-(3R,4R,5R,6S)-4,5,6-Tris-benzyloxy-7-(tert-butyl-diphenyl-silanyloxy)-1-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-hept-1-en-3-ol 
• 110316-55-7 (2R,3R,4R,5S,6R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-((Z)-2-iodo-vinyl)-tetrahydro-pyran 
• 443916-40-3 (R)-4-[1-Hydroxy-3-((2R,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester 
• 443916-02-7 6,10-anhydro-7,8,9,11-tetra-O-benzyl-2,3,4,5-tetradeoxy-1,2-N,O-isopropylidene-2-(tert-butoxycarbonylamino)-D-erythro-L-gulo-undecitol 
• 499135-05-6 (S)-2-tert-butoxycarbonylamino-5-(2',3',4',6'-tetra-O-benzyl-α-D-glucopyranosyl)-pent-4-ynoic acid methyl ester 
• 849359-28-0 2-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-1H-indole 
• 849359-36-0 2-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-L-(N-carbobenzyloxy)tryptophan 

Relevant articles and documents

MANNOSE DERIVATIVES FOR TREATING BACTERIAL INFECTIONS

The present invention relates to compounds useful for the treatment or prevention of bacteria infections. These compounds have formula (I). The invention also provides pharmaceutically acceptable compositions containing the compounds and methods of using the compositions in the treatment of bacteria infections. Finally, the invention provides processes for making compounds of the invention.

Stereocontrolled syntheses of α-C-mannosyltryptophan and its analogues

The total synthesis of α-C-mannosyltryptophan (C-Man-Trp), a naturally occurring C-glycosylamino acid, was achieved from a commercially available α-methyl-D-mannoside in 10 steps including the following key steps: the C-glycosidation of a mannose derivative with a stannylacetylene, Castro indole synthesis, and Sc(ClO4)3-promoted coupling with L-serine-derived aziridine carboxylate. The glucose- and galactose-analogues of C-Man-Trp were also synthesized in a similar manner. Conformational analyses of the synthesized C-glycosyltryptophan and its synthetic intermediate are briefly discussed.

Synthesis of α- and β-glycosyl asparagine ethylene isosteres (C-glycosyl asparagines) via sugar acetylenes and Garner aldehyde coupling

A convergent approach has been developed for the synthesis of C-glycosyl amino acids in which the glycinyl moiety CH(NH2)CO2H is connected to the anomeric center of the sugar residue by a three carbon atom tether. Essentially, these compounds are isosteres of N-glycosyl asparagines in which the amide group has been replaced by an ethylene bridge. Following the coupling of α- or β-D-linked lithium C-glycoside acetylides with N-Boc D-serinal acetonide (Garner aldehyde), the resulting adducts were transformed into the final N-Boc-C-glycosyl-α-aminopentanoic acids via reduction of the triple bond, deoxygenation, and oxidative cleavage of the oxazolidine ring. By this protocol, 12 C-glycosyl asparagines, six pairs of α- and β-anomers, have been prepared incorporating the gluco, galacto, manno, and the corresponding 2-acetamido-2-deoxy residues.