1352827-06-5

Basic information

• Product Name: methyl (4-O-benzoyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• Synonyms: methyl (4-O-benzoyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside
• CAS NO: 1352827-06-5
• Molecular Weight: 1001.18
• Mol File: 1352827-06-5.mol

Chemical Properties

• CAS DataBase Reference: methyl (4-O-benzoyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: methyl (4-O-benzoyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside(1352827-06-5)
• EPA Substance Registry System: methyl (4-O-benzoyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl)-(1→6)-2,3,4-tri-O-benzyl-α-D-glucopyranoside(1352827-06-5)

Safety Data

• Hazardous Substances Data: 1352827-06-5(Hazardous Substances Data)

Upstream product

• 53008-65-4 methyl 2,3,4-tri-O-benzyl-D-glucopyranoside 
• 1352826-99-3 4-O-benzoyl-2,3,6-tri-O-benzyl-α-D-glucopyranosyl bromide 
• 98-88-4 benzoyl chloride 
• 141263-02-7 ethyl 2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 2936-70-1 (2R,3S,4S,5R,6S)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol 
• 13992-16-0 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate 
• 83-87-4 D-glucose pentaacetate 
• 97974-20-4 (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol 
• 87470-70-0 S-phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-β-D-glucopyranoside 
• 71676-30-7 (2R,4aR,6S,7R,8R,8aS)-2-Phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol 
• 1352827-02-1 ethyl 4-O-benzoyl-2,3,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 

Relevant articles and documents

Halobenzoyl groups in glycosylation: Effect on stereoselectivity and reactivity of glycosyl donors

Described herein is the synthesis and evaluation of a series of glycosyl donors equipped with halobenzoyl substituents at O(4) and O(6) to study their properties in glycosylations. Among possible effects that may include carbonyl participation or H-bond m

Directing effect by remote electron-withdrawing protecting groups at O-3 or O-4 position of donors in glucosylations and galactosylations

Glucosylations and galactosylations of various acceptors with donors possessing an electron-withdrawing benzylsulfonyl, benzoyl, or acetyl group at the O-3 or O-4 position were performed. A β-directing effect by the benzylsulfonyl group at O-3 of the glucosyl donors and by the benzylsulfonyl and acyl groups at O-4 of the glucosyl donors was observed. In contrast, acyl groups at O-3 of the glucosyl donors and acyl groups at O-3 and O-4 of the galactosyl donors exhibited an α-directing effect. The α-directing effect is partly considered to remote participation of the acyl groups, whereas the β-directing effect is somewhat attributed to the SN2-like reaction of the acceptor with the glycosyl triflate or the contact ion pair, which is stabilized by remote electron-withdrawing groups. Further evidence for the stability of the α-glycosyl triflates was determined by a low-temperature NMR study.

Glycosidation of thioglycosides in the presence of bromine: Mechanism, reactivity, and stereoselectivity

Elaborating on previous studies by Lemieux for highly reactive "armed" bromides, we discovered that β-bromide of the superdisarmed (2-O-benzyl-3,4,6-tri-O-benzoyl) series can be directly obtained from the thioglycoside precursor. When this bromide is glycosidated, α-glycosides form exclusively; however, the yields of such transformations may be low due to the competing anomerization into α-bromide that is totally unreactive under the established reaction conditions.

Effect of remote picolinyl and picoloyl substituents on the stereoselectivity of chemical glycosylation

O-Picolinyl and O-picoloyl groups at remote positions (C-3, C-4, and C-6) can mediate glycosylation reactions by providing high or even complete facial selectivity for the attack of the glycosyl acceptor. The set of data presented herein offers a strong evidence of the intermolecular H-bond tethering between the glycosyl donor and glycosyl acceptor counterparts while providing a practical new methodology for the synthesis of either 1,2-cis or 1,2-trans linkages. Challenging glycosidic linkages including α-gluco, β-manno, and β-rhamno have seen obtained with high or complete stereocontrol.