1-adamantanyl 2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-β-D-mannopyranoside

Base Information

Chemical Name:1-adamantanyl 2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-β-D-mannopyranoside
CAS No.:553663-12-0
Molecular Formula:C₄₆H₄₉IO₇S
Molecular Weight:872.861
Hs Code.:

Synonyms:1-adamantanyl 2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-β-D-mannopyranoside

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Chemical Property of 1-adamantanyl 2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-β-D-mannopyranoside

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Technology Process of 1-adamantanyl 2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-β-D-mannopyranoside

There total 3 articles about 1-adamantanyl 2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-β-D-mannopyranoside 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: 84.0%

: 768-95-6
1-adamanthanol

: 553663-00-6
S-phenyl 4,6-O-α-[2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside

: 553663-12-0
1-adamantanyl 2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-β-D-mannopyranoside

Guidance literature:: With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; molecular sieve; In dichloromethane; at -60 - 20 ℃; for 4h;
DOI:10.1021/ol034741r

Reference yield:

: 768-95-6
1-adamanthanol

: S-phenyl 4,6-O-α-[2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-2,3-di-O-benzyl-1-thio-α-D-mannopyranoside

: 553663-12-0
1-adamantanyl 2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-β-D-mannopyranoside

: (2R,4aR,6S,7S,8S,8aR)-6-(Adamantan-1-yloxy)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carbothioic acid S-[2-(2-iodo-phenyl)-ethyl] ester

Guidance literature:: With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; molecular sieve; In dichloromethane; at -60 - 20 ℃; for 4h; Title compound not separated from byproducts;
DOI:10.1021/ol034741r

Reference yield:

: 177748-62-8
2-(2-iodophenyl)-1-ethanethiol

: 553663-12-0
1-adamantanyl 2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: AlMe₃ / toluene; hexane / 0.5 h / 0 °C

1.2: 624 mg / toluene; hexane / 4 h / Heating

2.1: 1-benzenesulfinylpiperidine; 2,4,6-tri-tert-butylpyrimidine; triflic anhydride / CH₂Cl₂ / 0.17 h / -60 °C

2.2: 84 percent / CH₂Cl₂ / 4 h / -60 - 20 °C

With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; trimethylaluminum; 2,4,6-tri-tert-butylpyrimidine; In hexane; dichloromethane; toluene;
DOI:10.1021/ja048070j