78157-46-7

Basic information

• Product Name: benzyl (2S)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydropyran-2-yl]oxy-2-(tert-butoxycarbonylamino)propanoate
• Synonyms: benzyl (2S)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydropyran-2-yl]oxy-2-(tert-butoxycarbonylamino)propanoate
• CAS NO: 78157-46-7
• Molecular Weight: 624.642
• Mol File: 78157-46-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: benzyl (2S)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydropyran-2-yl]oxy-2-(tert-butoxycarbonylamino)propanoate(CAS DataBase Reference)
• NIST Chemistry Reference: benzyl (2S)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydropyran-2-yl]oxy-2-(tert-butoxycarbonylamino)propanoate(78157-46-7)
• EPA Substance Registry System: benzyl (2S)-3-[(2R,3R,4R,5S,6R)-3-acetamido-4,5-diacetoxy-6-(acetoxymethyl)tetrahydropyran-2-yl]oxy-2-(tert-butoxycarbonylamino)propanoate(78157-46-7)

Safety Data

• Hazardous Substances Data: 78157-46-7(Hazardous Substances Data)

Upstream product

• 136945-13-6 [(2R,3S,4R,5R)-3,4-diacetoxy-6-hydroxy-5-(2,2,2-trichloroethoxycarbonylamino)tetrahydropyran-2-yl]methyl acetate 
• 108-24-7 acetic anhydride 
• 59524-02-6 N-tert-butoxycarbonyl-L-serine benzyl ester 
• 136945-14-7 O-[3,4,6-tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl] trichloroacetimidate 
• 1078691-95-8 (+)-D-glucosamine hydrochloride 
• 100-39-0 benzyl bromide 
• 3262-72-4 (S)-N-(tert-butoxycarbonyl)serine 
• 193140-87-3 (S)-2-tert-Butoxycarbonylamino-3-[(2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-(4,5,6,7-tetrachloro-1,3-dioxo-1,3-dihydro-isoindol-2-yl)-tetrahydro-pyran-2-yloxy]-propionic acid benzyl ester 
• 193140-95-3 (S)-2-tert-Butoxycarbonylamino-3-((2R,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-diacetylamino-tetrahydro-pyran-2-yloxy)-propionic acid benzyl ester 
• 171973-78-7 Acetic acid (2R,3S,4R,5R,6S)-3-acetoxy-2-acetoxymethyl-5-diacetylamino-6-methylsulfanyl-tetrahydro-pyran-4-yl ester 
• 170873-76-4 O-<3,4,6-Tri-O-acetyl-2-deoxy-2-(3,4,5,6-tetrachlorophthalimido)-β-D-glucopyranosyl> trichloroacetimidate 
• 3068-34-6 Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-acetylamino-6-chloro-tetrahydro-pyran-4-yl ester 

Relevant articles and documents

SYNTHESIS OF A GLYCOTRIPEPTIDE AND A GLYCOSOMATOSTATIN CONTAINING THE 3-O-(2-ACETAMIDO-2-DEOXY-β-D-GLUCOPYRANOSYL)-L-SERINE RESIDUE

3-O-(2-Acetamido-3,4,6-tri-O-acetyl-2-deoxy-β-D-glucopyranosyl)-N-(tert-butyloxycarbonyl)-L-serine was synthesized and condensed by the solid-phase procedure to give the sequence Gly-3)-Ser>-Ala-OH and β-D-GlcpNAc-(1->3)-Ser-13-somatostat

Efficient synthesis of O-(2-acetamido-2-deoxy-β-D-glucopyranosyl)-serine and -threonine building blocks for glycopeptide formation

Glucosamine donors 1-3 having N-TCP, N,N-diacetyl and N-Teoc protection, respectively, give with Nα-Boc-protected serine and threonine benzyl esters 4a,b as acceptors exclusively the β-glycosides; they can be transformed into O-GIcNAc serine and threonine derivatives 8a,b. The high yielding O-glycosylation of compounds 4a,b with trichloroacetimidate 3 and the ease of replacement of the N-Teoc group by the N-acetyl group prompted the use of Nα-Fmoc-protected serine and threonine allyl (9a,b) and Pfp active esters (12a,b) as acceptors, thus very efficiently yielding the corresponding O-(N,O-acetylglucosamino) serine and threonine derivatives 11a.b and 14a,b as active esters.