Stereoselective synthesis of 2-hydroxy-α-mannopyranosides from glucal donors

Organic Letters

Volumn 3, Issue 2, 2001, Pages 303-306

  Kim, Ji Young ^a   Di Bussolo, Valeria ^a   Gin, David Y ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DISACCHARIDE; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; MONOSACCHARIDE; OLIGOSACCHARIDE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; SYNTHESIS;

CARBOHYDRATE CONFORMATION; DISACCHARIDES; INDICATORS AND REAGENTS; MOLECULAR STRUCTURE; MONOSACCHARIDES; OLIGOSACCHARIDES; OXIDATION-REDUCTION; STEREOISOMERISM;

EID: 0035945746     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006941y     Document Type: Article

References (45)

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38. It is unclear whether the activated sulfoxide intermediate 8 exists/ reacts as a sulfonium species or a σ-sulfurane species.
39. The use of excess DBTO served to minimize the formation of the unwanted byproduct 15, presumably a result of increased stabilization of the putative oxocarbenium intermediate arising from glycal activation (i.e., 9 → 10).
40. The corresponding benzylsulfilimine derivative 17 was also isolated as a byproduct, which is consistent with the presumed acceptor-induced epoxide ring closure in Scheme 4.
41. -), which assumes a sterically favorable α-approach onto the glucal (i.e., trans to the C(3)-substituent), leading to a net transfer of oxygen to the β-face of the glucal (Scheme 4). Attempts to identify the putative intermediates 9 and/or 10 are underway to gain insight into the validity of such a hypothesis.
42. In these reactions, 0.5 equiv of 2,4,6-tri-tert-butylpyridine can be introduced at the outset of the reaction to neutralize trace amounts of triflic acid that could potentially lead to unproductive glucal decomposition.
43. For the oxidative glycosylation of allyl alcohol with 3,4-di-O-benzyl-6-O-triisopropylsilyl-D-glucal, 7% of the corresponding 2-hydroxy-β-D-glucopyranoside was also isolated.
44. Although fairly unhindered secondary alcohols can be oxidatively mannosylated with this procedure, more hindered secondary alcohol acceptors, such as methyl 2,3,6-tri-O-benzyl-D-glucopyranose, were ineffective, presumably a result of inefficient addition of the nucleophile to the putative oxosulfonium salt 10 in the epoxide ring closure step. Efforts are currently underway to develop a procedure for the mannosylation of hindered acceptors by introducing a sacrificial nucleophile to form the intermediate anhydropyranoside prior to epoxide opening with the desired acceptor.
45. The excess carbohydrate acceptor can be recovered at the end of the reaction.