40246-33-1

Basic information

• Product Name: 3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
• Synonyms: 3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside
• CAS NO: 40246-33-1
• Molecular Weight: 692.804
• Mol File: 40246-33-1.mol
• Article Data: 31

Chemical Properties

• CAS DataBase Reference: 3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: 3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside(40246-33-1)
• EPA Substance Registry System: 3,4,6-tri-O-benzyl-β-D-glucopyranoside-(1->6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranoside(40246-33-1)

Safety Data

• Hazardous Substances Data: 40246-33-1(Hazardous Substances Data)

Upstream product

• 127299-77-8 Phenyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 84207-56-7 6-O-<(3'R,4'R,5'R)-5'-hydroxy-3',4',6'-tribenzyloxyhex-1'(Z)-enyl>-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 100-39-0 benzyl bromide 
• 3254-17-9 3,4,6-tri-O-acetyl-1,2-O-(1-ethoxyethylidene)-α-D-glucopyranose 
• 53270-12-5 1,2-O-(1-ethoxyethylene) 3,4,6-tri-O-benzyl-1-thio-α-D-glucopyranose 
• 331281-73-3 Dibutyl 3,4,6-tri-O-benzyl-2-O-para-chlorophenylcarbonyl-β-D-glucipyranosyl phosphate 
• 331281-74-4 Thioethyl 3,4,6-tri-O-benzyl-2-O-para-chlorophenylcarbonyl-β-D-glucopyranoside 
• 208656-41-1 Phosphoric acid (2S,3R,4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl ester dibutyl ester 
• 180187-58-0 ethyl 3,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside 
• 74372-90-0 3,4,6-tri-O-benzyl-D-glucal epoxide 
• 55628-54-1 3,4,6-tri-O-benzyl-D-glucal 
• 604767-65-9 Phosphoric acid (4R,5R,6R)-4,5-bis-benzyloxy-6-benzyloxymethyl-3-hydroxy-tetrahydro-pyran-2-yl ester dibutyl ester 
• 1011723-04-8 glucal epoxide 
• 4064-06-6 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 

Downstream Products

• 135192-35-7 O-(3,4,6-tri-O-benzyl-2-O-<(pentafluorophenoxy)thiocarbonyl>-β-D-glucosyl)-(1<*>6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 51532-76-4 2-O-acetyl-3,4,6-tri-O-benzyl-β-D-glucopyranosyl(1→6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 121399-46-0 1,2:3,4-di-O-isopropylidene-6-O-(3,4,6-tri-O-benzyl-2-O-(methylthio)thiocarbonyl-β-D-glucopyranosyl)-α-D-galactopyranose 
• 213028-97-8 6-O-(3,4,6-tri-O-benzyl-2-O-trifluoromethanesulfonyl-β-D-glucopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 40246-34-2 (2R,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-((3aR,5R,5aS,8aS,8bR)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-5-ylmethoxy)-dihydro-pyran-3-one 
• 112330-11-7 (3,4,6-tri-O-benzyI-β-D-mannopyranosyl)-(1→6)-1,2,3,4-di-O-isoprpopylidene-α-D-galactopyranoside 
• 153947-47-8 6-O-(2-O-acetyl-3,4,6-tri-O-benzyl-β-D-mannopyranosyl)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 
• 79384-22-8 O-(3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyl)-(1[*]6)-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose 

Relevant articles and documents

Photolabile 2-(2-Nitrophenyl)-propyloxycarbonyl (NPPOC) for Stereoselective Glycosylation and Its Application in Consecutive Assembly of Oligosaccharides

A photolabile protecting group (PPG) 2-(2-nitrophenyl)-propyloxycarbonyl (NPPOC) was explored in glycosylation and applied in the consecutive synthesis of oligosaccharides. NPPOC displays a strong neighboring group participation (NGP) effect to facilitate the construction of 1,2-trans glycosides in excellent yield. Notably, NPPOC could be efficiently removed by photolysis, and the deprotection conditions are friendly to typical protecting groups. A branched and asymmetric oligomannose Man6 was rapidly prepared, and the consecutive assembly of oligosaccharides without intermediate purification was further investigated owing to the compatibility conditions between NPPPOC's photolysis and glycosylation.

Cyanomethyl Ether as an Orthogonal Participating Group for Stereoselective Synthesis of 1,2-trans-β-O-Glycosides

Stereoselective formation of glycosidic linkages has been the prime focus for contemporary carbohydrate chemistry. Herein, we report cyanomethyl (CNMe) ether as an efficient and effective participating orthogonal protecting group for the stereoselective synthesis of 1,2-trans-β-O-glycosides. The participating group facilitated good to high β-selective glycosylation with a broad range of electron-rich and electron-deficient glycosyl acceptors. Detailed experimental and theoretical studies reveal the involvement of CNMe ether in the formation of a six-membered imine-type cyclic intermediate for the observed stereoselectivity. Rapid incorporation and selective removal of the CNMe ether group in the presence of benzyl ether and isopropylidene acetal protection have also been reported here. The nitrile group provided an opportunity for the glycodiversification through further derivatizations.

Neighbouring group participation during glycosylation: Do 2-substituted ethyl ethers participate?

The development of new protecting groups that undergo neighbouring group participation (NGP) via six-membered ring intermediates to promote the formation of α-1,2-cis glycosidic linkages complements the established use of 5-ring NGP in terms of stereochem