104495-20-7

Basic information

• Product Name: 2,3,4-tris-O-(phenylmethyl)-α-L-rhamnopyranosyl fluoride
• Synonyms: 2,3,4-tris-O-(phenylmethyl)-α-L-rhamnopyranosyl fluoride
• CAS NO: 104495-20-7
• Molecular Weight: 436.523
• Mol File: 104495-20-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 2,3,4-tris-O-(phenylmethyl)-α-L-rhamnopyranosyl fluoride(CAS DataBase Reference)
• NIST Chemistry Reference: 2,3,4-tris-O-(phenylmethyl)-α-L-rhamnopyranosyl fluoride(104495-20-7)
• EPA Substance Registry System: 2,3,4-tris-O-(phenylmethyl)-α-L-rhamnopyranosyl fluoride(104495-20-7)

Safety Data

• Hazardous Substances Data: 104495-20-7(Hazardous Substances Data)

Upstream product

• 73-34-7 L-rhamnose 
• 153745-67-6 phenyl 2,3,4-tri-O-acetyl-1-thio-β-L-rhamnopyranoside 
• 153745-68-7 phenyl 1-thio-L-rhamnopyranoside 
• 86795-38-2 2,3,4-tri-O-(phenylmethyl)-α-L-rhamnopyranoside 
• 7404-35-5 1,2,3,4-tetra-O-acetyl-L-rhamnopyranose 
• 210426-02-1 2,3,4-tri-O-benzyl-L-rhamnopyranose 

Downstream Products

• 175275-67-9 1-acetoxy-5-benzyloxy-4-methoxy-3-(2,3,4-tri-O-benzyl-β-L-rhamnopyranosyl)naphthalene 
• 175165-90-9 1-acetoxy-5-benzyloxy-4-methoxy-3-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyl)naphthalene 
• 172316-14-2 5-benzyloxy-4-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyloxy)-1-naphthyl 3-methoxy-5-<1-(2-(methoxymethoxy)ethyl)>-2-(trifluoromethanesulfonyloxy)benzoate 
• 172316-15-3 1-benzyloxy-10-methoxy-8-<1-(2-(methoxymethoxy)ethyl)>-12-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyloxy)-6H-benzonaphtho<1,2-b>pyran-6-one 
• 175165-89-6 Acetic acid 10-methoxy-8-[2-(2-nitro-phenylselanyl)-ethyl]-6-oxo-12-((2S,3R,4R,5S,6S)-3,4,5-triacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6H-dibenzo[c,h]chromen-1-yl ester 
• 157849-02-0 5-benzyloxy-4-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyloxy)-1-naphthyl-3-methoxy-5-methyl-2-(trifluoromethanesulfonyloxy)benzoate 
• 157849-03-1 1-benzyloxy-10-methoxy-8-methyl-12-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyloxy)-6H-benzonaphtho<1,2-b>pyran-6-one 
• 157849-01-9 5-benzyloxy-4-(2,3,4-tri-O-benzyl-α-L-rhamnopyranosyloxy)-1-naphthol 
• 132417-96-0 BE-12406 A 
• 294203-78-4 (2R,3S,4S)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-chroman-4-ol 
• 294203-79-5 (2R,3R)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-chroman-4-one 
• 29838-67-3 astilbin 
• 294203-76-2 (2R,3S)-5,7-Bis-benzyloxy-2-(3,4-bis-benzyloxy-phenyl)-3-((2S,3R,4R,5S,6S)-3,4,5-tris-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy)-chroman 
• 141883-04-7 C₅₉H₇₄O₁₄ 

Relevant articles and documents

Electrochemical Synthesis of Glycosyl Fluorides Using Sulfur(VI) Hexafluoride as the Fluorinating Agent

This manuscript describes the electrochemical synthesis of 17 different glycosyl fluorides in 73-98% yields on up to a 5 g scale that relies on the use of SF6 as an inexpensive and safe fluorinating agent. Cyclic voltammetry and related mechanistic studies carried out subsequently suggest that the active fluorinating species generated through the cathodic reduction of SF6 are transient under these reductive conditions and that the sulfur and fluoride byproducts are effectively scavenged by Zn(II) to generate benign salts.

Total syntheses of Be-12406 a and its C(8)-Vinyl analog

Total syntheses of BE-12406 A (3a) and its C(8)-vinyl analog (3c) are described. The key step is the selective O-glycosylation of naphthol (4)with L-rhamnopyranosyl fluoride (5) by employing Cp2HfCl2-AgClO4 in fluorobenzene at -20°C in the presence of a hindered base, 2,6-di-t-butyl-4-methylpyridine (12), affording O-glycoside (11) in good yield.