136174-75-9

Upstream product

• 185836-62-8 3-[(2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-(naphthalen-2-yloxy)-tetrahydro-pyran-3-ylsulfanyl]-4-methyl-pent-3-en-2-one 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 135-19-3 β-naphthol 
• 152420-91-2 1-O,2-S-(2-acetyl-1-methyl-1,2-ethenediyl)-3,4,6-tri-O-benzyl-2-thio-α-D-glucopyranose 
• 139378-91-9 (2S,3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-(4-methoxy-phenylsulfanyl)-tetrahydro-pyran-2-ol 
• 122194-14-3 (3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-phenylselanyl-tetrahydro-pyran-2-ol 
• 117901-42-5 (3R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-phenylsulfanyl-tetrahydro-pyran-2-ol 
• 144100-89-0 C₃₈H₄₇N₂O₇PS 
• 136174-73-7 2-naphthyl 2-deoxy-2-selenophenyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 136174-72-6 2-naphthyl 2-deoxy-2-thiophenyl-3,4,6-tri-O-benzyl-β-D-glucopyranoside 
• 185836-58-2 (4aR,6R,7R,8S,8aR)-7,8-Bis-benzyloxy-6-benzyloxymethyl-2-isopropenyl-3-methyl-6,7,8,8a-tetrahydro-4aH-4,5-dioxa-1-thia-naphthalene 
• 144101-03-1 (2R,3R,4S,5R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-5-(4-methoxy-phenylsulfanyl)-6-(naphthalen-2-yloxy)-tetrahydro-pyran 

Relevant academic research and scientific papers

Reagent-Controlled Stereoselective Glycosylation

Provided are methods for the efficient stereoselective formation of glycosidic bonds, without recourse to prosthetic or directing groups.

Reagent controlled β-specific dehydrative glycosylation reactions with 2-deoxy-sugars

N-Sulfonyl imidazoles activate 2-deoxy-sugar hemiacetals for glycosylation presumably by converting them into glycosyl sulfonates in situ. By matching the leaving group ability of the sulfonate with the reactivity of the donor, it is possible to obtain β-

Synthetic approaches to the angucycline antibiotics. A route to C-glycosidic benz[a]anthraquinones

3-Deoxy-6′-hydroxy-13-norurdamycinone B (32a) and 3-deoxy-13-norurdamycinone B (32b) have been synthesized in eight steps from 5,8-dimethoxynaphthalen-1-ol (9) both in 28% overall yield. The key step in this approach is the boron trifluoride diethyl ether

Novel Bicylic Donors for the Synthesis of 2-Deoxy-β-Glycosides

Novel bicyclic glycosyl donors have been prepared by the cycloaddition reaction of glycals with 3-thiono-2,4-pentanedione 17 followed by methylenation of the resulting ketone. Treatment of the heterocyclic donors with triflic acid in the presence of a variety of alcohol acceptors leads to the formation of β-glycosides in good yields and with excellent stereoselectivities. Desulfurization of the C-2 carbon-sulfur bonds gives the corresponding 2-deoxy-β-glycosides. This method has been extended to the synthesis of glycosidic linkages found in the aureolic acid antibiotics. Tetra-N-butylammonium triflate proved to be a useful additive in these glycosylation reactions, suggesting an important role for triflate anion in stabilizing intermediates which are formed.

Studies on the synthesis of aureolic acid antibiotics: Highly stereoselective synthesis of aryl 2-deoxy-β-glycosides via the Mitsunobu reaction and synthesis of the olivomycin A-B disaccharide

The Mitsunobu reaction of phenols and 1,2-cis-2-thiophenyl-α-D-glycopyranoses or 1,2-cis-2-selenophenyl-α-D-glycopyranoses is a very effective method for the highly stereoselective synthesis of aryl 2-deoxy-β-D-glycosides. The equatorial 2-thiophenyl or 2

A Stereocontrolled Construction of 2-Deoxy-β-glycosidic Linkages via 1,2-trans-β-Glycosidation of 2-Deoxy-2-glycopyranosyl N,N,N',N'-Tetramethylphosphoroamidates

A stereocontrolled synthesis of 2-deoxy-β-glycosides has been achieved by developing a salient 1,2-trans-glycosidation method with 2-deoxy-2-glycopyranosyl N,N,N',N'-tetramethylphosphoroamidates as glycosyl donors followed by a redu