85422-87-3

Basic information

• Product Name: 1-phenyl-2-((2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)ethan-1-one
• Synonyms: 1-phenyl-2-((2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)ethan-1-one
• CAS NO: 85422-87-3
• Molecular Weight: 642.792
• Mol File: 85422-87-3.mol
• Article Data: 9

Chemical Properties

• CAS DataBase Reference: 1-phenyl-2-((2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)ethan-1-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-phenyl-2-((2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)ethan-1-one(85422-87-3)
• EPA Substance Registry System: 1-phenyl-2-((2R,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)ethan-1-one(85422-87-3)

Safety Data

• Hazardous Substances Data: 85422-87-3(Hazardous Substances Data)

Upstream product

• 13735-81-4 1-styrenyloxytrimethylsilane 
• 74808-09-6 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate 
• 74352-41-3 2-Pyridyl 2,3,4,6-tetra-O-benzyl-1-thio-β-D-galactopyranoside 
• 53008-64-3 Toluene-4-sulfonic acid (2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester 
• 98-86-2 acetophenone 
• 4291-69-4 2,3,4,6-Tetra-O-benzyl-D-glucopyranose 
• 25320-59-6 tetra-O-benzyl glucopyranosyl chloride 
• 14990-66-0 1-(1-phenylvinyl)piperidine 
• 14548-16-4 Dimethyl-(1-phenyl-vinyl)-amine 

Downstream Products

• 99701-84-5 3-Dimethylamino-1-phenyl-2-(2,3,4,6-tetra-O-benzyl-α,β-D-glucopyranosyl)-2-propen-1-on 
• 81972-20-5 2-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)ethanol 
• 85422-88-4 1-phenyl-2-(3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)ethan-1-one 
• 96689-92-8 α-1-deoxy-1-(C-1'-phenethyl)-2,3,4,6-tetra-O-acetyl-D-glucopyranose 
• 85422-91-9 α-1-deoxy-1-(C-1'-phenethyl)-2,3,4,6-tetra-O-acetyl-D-glucopyranose 
• 85505-09-5 2,3,4,6-O-tetra-acetyl-1-deoxy-1-(2-phenylethyl)-β-D-glucopyranose 
• 99701-82-3 3-Phenyl-4-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)pyrazol 
• 99701-81-2 3-Phenyl-4-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)pyrazol 
• 99701-87-8 2-Amino-4-phenyl-5-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)pyrimidin 
• 99701-86-7 2-Amino-4-phenyl-5-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)pyrimidin 
• 99701-85-6 2-Methyl-4-phenyl-5-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)pyrimidin 

Relevant articles and documents

Mild cu(Otf)2-mediated C-glycosylation with chelation-assisted picolinate as a leaving group

C-Glycosylation reactions of glycosyl picolinates with allyltrimethylsilane or silyl enol ethers were developed. Picolinate as a chelation-assisted leaving group could be activated by Cu(OTf)2 and avoided the use of harsh Lewis acids. The glycosylations were operated under mild neutral conditions and gave the corresponding C-glycosides in up to 95% yield with moderate to excellent stereoselectivities.

The mukaiyama type aldol reaction for the synthesis of: Trans-2,6-disubstituted tetrahydropyrans: Synthesis of diospongin a and b

An efficient synthesis protocol for the preparation of trans-2,6-disubstituted tetrahydropyrans by the reaction of 1-phenyl-1-triemthylsiloxyethylene with six membered cyclic hemiacetals in the presence of iodine is developed. This reaction proceeds smoothly under mild conditions employing a catalytic amount of molecular iodine. The feature of this novel conversion includes milder reaction conditions, broader substrate scope, functional group tolerance and good diastereoselectivity. The efficiency and practicality of the current method were successfully displayed in the total synthesis of diospongin A and B in good yields.

C-Glucopyranosyl derivatives from readily available 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl chloride

-