benzenesulfenyl triflate

Base Information

• Chemical Name: benzenesulfenyl triflate
• CAS No.: 84224-65-7
• Molecular Formula: C₇H₅F₃O₃S₂
• Molecular Weight: 258.242
• Mol file: 84224-65-7.mol

Synonyms:benzenesulfenyl triflate

Chemical Property of benzenesulfenyl triflate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzenesulfenyl triflate

There total 1 articles about benzenesulfenyl triflate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

silver trifluoromethanesulfonate (2923-28-6) + benzenesulfenyl chloride (931-59-9) → benzenesulfenyl triflate (84224-65-7)

Guidance literature:

at -30 ℃; for 1h;

Reference yield: 17.0%

benzenesulfenyl triflate (84224-65-7) + 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (4064-06-6) + phenyl 2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-1-thio-α-D-mannopyranoside (263543-43-7) → 2,6-di-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-α/β-D-mannopyranose + 6-O-[2,6-di-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-β-D-mannopyranosyl]-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose + 6-O-[2,6-di-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-mannopyranosyl]-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose

Guidance literature:

benzenesulfenyl triflate; phenyl 2,6-di-O-benzyl-3,4-O-[(2S,3S)-2,3-dimethoxybutan-2,3-diyl]-1-thio-α-D-mannopyranoside; With 2,6-di-tert-butyl-4-methylpyridine; In dichloromethane; at -78 ℃; for 0.25h;

1,2:3,4-di-O-isopropylidene-α-D-galactopyranose; In dichloromethane; at -78 ℃; for 2h;

DOI:10.1021/jo9910482

Reference yield: 15.0%

(2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol (2774-19-8,14419-69-3,15887-67-9,23392-28-1,57539-08-9,61277-63-2,74410-51-8,76419-48-2,80734-73-2,86363-44-2,89301-79-1,94061-92-4,94062-87-0,108739-92-0,129706-93-0,143005-12-3,65877-21-6) + benzenesulfenyl triflate (84224-65-7) + S-ethyl 2,6-di-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thia-α-D-mannopyranoside (201211-99-6) → 2,6-di-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-α/β-D-mannopyranose + methyl 3-O-benzyl-2-O-[2,6-di-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-β-D-mannopyranosyl]-4,6-O-benzylidene-α-D-mannopyranoside + methyl 3-O-benzyl-2-O-[2,6-di-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-α-D-mannopyranosyl]-4,6-O-benzylidene-α-D-mannopyranoside

Guidance literature:

benzenesulfenyl triflate; S-ethyl 2,6-di-O-benzyl-3,4-O-(2',3'-dimethoxybutane-2',3'-diyl)-1-thia-α-D-mannopyranoside; With 2,6-di-tert-butyl-4-methylpyridine; In dichloromethane; at -78 ℃; for 0.25h;

(2R,4aR,6S,7S,8R,8aR)-8-Benzyloxy-6-methoxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol; In dichloromethane; at -78 ℃; for 2h;

DOI:10.1021/jo9910482

upstream raw materials:

silver trifluoromethanesulfonate

benzenesulfenyl chloride

Downstream raw materials:

Trifluoro-methanesulfonic acid (2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl triflate

Refernces

• 1、 Crich, David,Sun, Sanxing. "Are glycosyl triflates intermediates in the sulfoxide glycosylation method? A chemical and 1H, 13C, and 19F NMR spectroscopic investigation". . p. 11217 - 11223. Retrieved 2007/10/03.