128442-04-6

Upstream product

• 128848-52-2 phenyl 3-O-benzyl-4,6-O-benzylidene-2-O-trimethylsilyl-1-thio-β-D-glucopyranoside 
• 496019-46-6 (2R,6S,7R,8S,8aS)-7,8-bis(benzyloxy)-2-phenyl-6-(phenylthio)hexahydropyrano[3,2-d][1,3]dioxine 
• 63598-36-7 4,6-O-benzylidene-D-glucal 
• 100-39-0 benzyl bromide 
• 884844-04-6 ethyl 3-O-benzyl-4,6-O-benzylidene-2-O-(methylsulfonyl)-1-thio-β-D-glucopyranoside 
• 930-69-8 sodium thiophenolate 
• 5188-07-8 sodium thiomethoxide 
• 1204197-72-7 ethyl 3-O-benzyl-4,6-O-benzylidene-2-O-methanesulfonyl-1-thio-α-D-mannopyranoside 
• 63598-38-9 1,5-anhydro-4,6-O-benzylidene-2-deoxy-D-ribo-hex-1-enopyranose 
• 1125-88-8 benzaldehyde dimethyl acetal 
• 134756-58-4 S-phenyl 4,6-O-benzylidene-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside 
• 111425-49-1 phenyl 4,6-di-O-acetyl-2,3-dideoxy-1-thio-α-D-erythro-hex-2-enopyranoside 
• 111425-52-6 thiophenyl 2,3-dideoxy-α-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 

Downstream Products

• 124718-59-8 (2R,3R,4S,5S,6S)-4-Benzyloxy-2-hydroxymethyl-6-methoxy-5-phenylsulfanyl-tetrahydro-pyran-3-ol 
• 124718-58-7 (2R,3R,4S,5R,6R)-4-Benzyloxy-2-hydroxymethyl-6-methoxy-5-phenylsulfanyl-tetrahydro-pyran-3-ol 
• 139490-71-4 (2R,4aR,6S,7S,8S,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-7-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 139490-70-3 (2R,4aR,6R,7R,8S,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-7-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine 
• 128358-62-3 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-iodo-β-D-altropyranosyl benzenesulfonamide 
• 128358-62-3 3-O-benzyl-4,6-O-benzylidene-2-deoxy-2-iodo-α-D-altropyranosyl benzenesulfonamide 
• 139378-96-4 6'-(1',2':3',4'-diisopropylidenegalactopyranosyl) 3-O-benzyl-2-deoxy-2-(phenylthio)-β-D-glucopyranoside 
• 139523-60-7 6'-(1',2':3',4'-diisopropylidenegalactopyranosyl) 3-O-benzyl-2-deoxy-2-(phenylthio)-α-D-mannopyranoside 
• 134756-68-6 O-<2-benzenesulfonamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-allopyranosyl>-β-(1->4)-6-O-benzyl-2-bromo-2-deoxy-3-O-<<2-(trimethylsilyl)ethoxy>methyl>-α-D-altropyranosyl benzenesulfonamide 
• 134756-67-5 O-<2-benzenesulfonamido-3-O-benzyl-4,6-O-benzylidene-2-deoxy-D-allopyranosyl>-β-(1->4)-1,5-anhydro-6-O-benzyl-2-deoxy-3-O-<<2-(trimethylsilyl)ethoxy>methyl>-D-ribo-hex-1-enopyranose 
• 183989-01-7 2-Trimethylsilanyl-ethanesulfonic acid [(2R,4aR,6R,7R,8S,8aS)-6-((4aS,6R,7R,7aR)-5-benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-yloxy)-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-amide 
• 183989-02-8 N-[(2R,4aR,6R,7R,8S,8aS)-6-((4aS,6R,7R,7aR)-5-Benzhydryl-6-benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxino[5,4-b]pyrrol-7-yloxy)-8-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl]-acetamide 
• 183989-04-0 2-Trimethylsilanyl-ethanesulfonic acid {(2R,4aR,6S,7R,8S,8aS)-8-benzyloxy-6-[(2R,3S,4S)-2-benzyloxymethyl-4-(2-trimethylsilanyl-ethoxymethoxy)-3,4-dihydro-2H-pyran-3-yloxy]-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl}-amide 
• 183989-00-6 2-Trimethylsilanyl-ethanesulfonic acid ((2R,4aR,6S,7S,8R,8aR)-8-benzyloxy-7-bromo-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl)-amide 

Relevant academic research and scientific papers

Reactions of phenyl and ethyl 2-O-sulfonyl-1-thio-α-d-manno- and β-d-glucopyranosides with thionucleophiles

Persubstituted derivatives of phenyl and ethyl 2-O-sulfonyl-1-thio-α-d-manno- and β-d-glucopyranosides were synthesized and reacted either with PhSNa or with MeSNa. The phenyl-1-thio compounds afforded the dithio-1,2-cis-axial/equatorial-α-d-glucopyranosi

Synthesis of saponins with cholestanol, cholesterol, and friedelanol as aglycones

Procedures for the synthesis of branched Xylss(1→3)[Galss- (1→2)]-Glc and Xylss(1→3)[Galss(1→2)]-GlcUA trisaccharides ss-linked to the 3-O of cholesterol, cholestanol, and friedelanol, respectively, were developed. To this end, ss-selective glucosylation

Efficient methods for glycosidations with glycals - A key intermediate for the synthesis of mucin core 1-type O-glycan

The use of glycals as acceptors in glycosylation reactions is hampered by their sensitivity to acids. We report here on the successful use of mild Lewis acid [Sn(OTf)2] as catalyst for the glycosylation with O-glycosyl trichloroacetimidates and on the development of this method to construct a key intermediate for the synthesis of mucin type O-glycans. To this end, chemoselective nitration of O-glycosylated glycals, stereoselective threonine addition, and reduction of the nitro group to the amino group by an efficient procedure avoiding the use of an expensive catalyst was performed.

The total synthesis of allosamidin. Expansions of the methodology of azaglycosylation pursuant to the total synthesis of allosamidin. A surprising enantiotopic sense for a lipase-induced deacetylation

Allosamidin, recently isolated from mycelial extracts of Streptomyces sp. 1713, is a powerful and selective chitinase inhibitor. The total synthesis of allosamidin is described herein. The electric eel acetylcholinesterase-mediated enantioselective hydrolysis of (trans,trans)-2-(benzyloxy)cyclopentene-1,3-diol diacetate accessed a monoacetyl derivative. Five additional steps produced a protected version of the aglycon ('allosamizoline') sector of allosamidin. An allal derivative stereoselectively reacted with benzenesulfonamide in the presence of a halonium source to afford a 2β-halo-1α-sulfonamidohexose. Treatment of this product with a strong base generated an intermediate 1,2-sulfonylaziridine, which was trapped with a protected allal derivative to provide a disaccharide glycal. Reiteration of this scheme gave access to the required trisaccharide. Following deprotection, the total synthesis of allosamidin was accomplished. In addition, the method, with modification, gave access to several allosamidin analogs.

A NOVEL 1,3 O -> C SILYL REARRANGEMENT IN CARBOHYDRATE CHEMISTRY: SYNTHESIS OF α-D-GLYCOPYRANOSYLTRIMETHYLSILANES

Reductive lithiation of 2-O-trimethylsilyl derivatives of phenyl thiogluco and -galactopyranosides gives rise to a 1,3 O -> C silyl migration leading to α-D-gluco and -galactopyranosyltrimethylsilanes in good yields.The expected β-elimination is observed

PREPARATION OF PYRANOID GLYCAL DERIVATIVES FROM PHENYL THIOGLYCOSIDES AND GLYCOSYL PHENYL SULPHONES

Phenyl thioglycopyranosides with various protecting groups (acetal, ether, ester) underwent reductive lithiation at C-1, followed by rapid elimination of the 2-substituent, when treated with lithium naphthalenide in tetrahydrofuran at low temperature.Thus

CONVENIENT SYNTHESES OF SUBSTITUTED PYRANOID GLYCALS FROM THIOPHENYL GLYCOSIDES AND GLYCOSYL PHENYLSULFONES

A series of substituted thiophenyl glycosides and glycosyl phenylsulfones were converted in high yield into glycals after reductive lithiation with lithium naphthalenide, followed by elimination of the substituent at C-2.