4132-32-5

Upstream product

• 38184-10-0 phenyl 2,3,4,5-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 544-97-8 dimethyl zinc(II) 
• 62774-37-2 phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-glucopyranoside 
• 352020-73-6 (2S,3S,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)-2-methyltetrahydro-2H-pyran-2-ol 
• 187226-51-3 phenyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-mannopyranoside 
• 79258-18-7 (2R,3R,4R,5S)-1,3,4,5-tetrakis(benzyloxy)hept-6-en-2-ol 
• 116417-40-4 butyl 2,3,4,6-tetra-O-benzyl-1-thio-α-D-glucopyranoside 
• 116417-39-1 butyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-glucopyranoside 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 75-24-1 trimethylaluminum 
• 126709-14-6 1-Azi-2,3,4,6-tetra-O-benzyl-1-deoxy-D-glucopyranose 
• 97321-68-1 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-phenylseleno-D-glycero-D-ido-heptitol 

Relevant academic research and scientific papers

Mercuricyclisation in Carbohydrate Chemistry: A Highly Stereoselective Route to α-D-C-Glucopyranosyl Derivatives

Mercuricyclisation of an olefin which is prepared from the carbohydrate 2,3,4,6-tetra-O-benzyl-D-glucopyranose using a Wittig reaction provides the axial chloromercuri-ether as the only isolated product, thus offering the first stereospecific route to 1,5

An efficient synthesis of β-C-glycosides based on the conformational restriction strategy: Lewis acid promoted silane reduction of the anomeric position with complete stereoselectivity

(Chemical Equation Presented) The reduction of glyconolactols having an anomeric carbon substituent by Et3SiH/TMSOTf proceeded with complete stereoselectivity to produce the corresponding β-C-glycosides when the substrates were conformationally restricted in the 4C 1-chair form by a 3,4-O-cyclic diketal or a 4,6-O-benzylidene protecting group. Thus, the efficient construction of β-C-glycosides was achieved on the basis of the conformation restriction strategy.

Glycosylidene carbenes. Part 29. Insertion into B-C and Al-C bonds: Glycosylborinates, -boranes, and -alanes

Insertion of the glycosylidene carbenes derived from the diazirines 1, 14, and 15 into the B-alkyl bond of the B-alkyl-9-oxa-10- borabicyclo[3.3.2]decanes 5, 6, and 7 yielded the stable glycosylborinates 8/9 (55%, 55:45), 10/11 (31%, 65:35), 12/13 (47%, 60:40), 16/17 (55%, 55:45), 18/19 (47%, 45:55), and 20/21 (31%, 30:70). Crystal-structure analysis of 17 and NOEs of 9 and 19 show that 17, 9, and 19 adopt similar conformations. The glycosylborinates are stable under acidic, basic and thermal conditions. The unprotected glycosylborinate 25 was obtained in 80% by hydrogenolysis of 12. Insertion of the glycosylidene carbene derived from the diazirine 1 into a B- C bond of BEt3, BBu3, and BPh3 led to unstable glycosylboranes that were oxidised to yield the hemiacetals 29 (55%), 31 (45%), and 33 (48%), respectively, besides the glucals 30 (13%), 32 (20%), and 34 (20%), respectively. Insertion of the glycosylidene carbenes derived from 14 and 15 into a B-C bond of BEt3 led exclusively to hemiacetals; only 15 yielding traces of the glucal 40 besides the hemiacetal 39. The glycosylidene carbene derived from 1 reacted with Al((i)Bu)3 and AlMe3 to generate reactive glycosylalanes that were hydrolysed, yielding the C-glycosides 46 (21%) and 49 (30%), respectively, besides the glucals 48 (26%) and 51 (30%); deuteriolysis instead of protonolysis led to the monodeuterio analogues of 46 and 49, respectively, which possess an equatorial 2H-atom at the anomeric center.

ORGANOMETALLICS IN ORGANIC SYNTHESIS. APPLICATIONS OF A NEW DIORGANOZINC REACTION TO THE SYNTHESIS OF C-GLYCOSYL COMPOUNDS WITH EVIDENCE FOR AN OXONIUM-ION MECHANISM

The mechanistic and stereochemical features of a new organozinc-based substitution process 1,R2)-SPh + R32Zn --> heteroatom-C-(R1,R2,R3)>, first discovered during a total synthesis of the alkaloid mycotoxin α-cyclopiazonic acid, are described.Phenyl thioglycosides were valuable substrates in studying the nature of this reaction process.Since these sulfur compounds are converted into C-glycosyl compounds with some degree of stereoselectivity, the organozinc chemistry does provide a new entry to these biologically active substances.

USE OF SELENIUM IN CARBOHYDRATE CHEMISTRY: PREPARATION OF C-GLUCOSIDE CONGENERS

3,4,5,7-Tetra-O-benzyl-D-gluco-hept-1-enitol was submitted to a selenocyclisation-oxidation-elimination sequence to provide 2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-D-gluco-hept-1-enitol in 54percent yield.Treatment of methyl 2,3,4-tri-O-benzyl-α-D-gluc