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

Base Information

Chemical Name:S-ethyl 2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]ethylidene-1-thio-α-D-mannopyranoside
CAS No.:887699-66-3
Molecular Formula:C₃₃H₃₇IO₆S₂
Molecular Weight:720.69
Hs Code.:

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

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Chemical Property of S-ethyl 2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]ethylidene-1-thio-α-D-mannopyranoside

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Technology Process of S-ethyl 2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]ethylidene-1-thio-α-D-mannopyranoside

There total 1 articles about S-ethyl 2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]ethylidene-1-thio-α-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:

: 152964-72-2
ethyl 2,3-di-O-benzyl-1-thio-α-D-mannopyranoside

: 887699-66-3
S-ethyl 2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]ethylidene-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 20 percent / BF₃*Et₂O / acetonitrile / 4 h / 20 °C

2: 76 percent / AlMe₃ / hexane; toluene / 6 h / 20 °C

With boron trifluoride diethyl etherate; trimethylaluminum; In hexane; toluene; acetonitrile;
DOI:10.1021/jo0526688

Reference yield: 80.0%

: 887699-66-3
S-ethyl 2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]ethylidene-1-thio-α-D-mannopyranoside

: 14133-63-2
methyl 2,3-O-isopropylidene-α-L-rhamnoside

: 887699-67-4
methyl 4-O-(2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]ethylidene-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranoside

Guidance literature:: S-ethyl 2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]ethylidene-1-thio-α-D-mannopyranoside; With molecular sieve; 1,1'-sulfinylbisbenzene; 2,4,5-tri-tert-butylpyrimidine; trifluoromethylsulfonic anhydride; In dichloromethane; at -70 ℃; for 0.5h;

methyl 2,3-O-isopropylidene-α-L-rhamnoside; In dichloromethane; at -70 ℃; for 2h;
DOI:10.1021/jo0526688

Reference yield:

: 887699-66-3
S-ethyl 2,3-di-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]ethylidene-1-thio-α-D-mannopyranoside

: methyl 4-O-(2,3-di-O-benzyl-β-D-rhamnopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: Ph₂SO; tri-tert-butylpyrimidine; molecular sieves / triflic anhydride / CH₂Cl₂ / 0.5 h / -70 °C

1.2: 80 percent / CH₂Cl₂ / 2 h / -70 °C

2.1: AIBN; Bu₃SnH / toluene / 4 h / Heating

2.2: 74 percent / NaOMe / methanol / 1 h / 20 °C

With molecular sieve; 2,2'-azobis(isobutyronitrile); 1,1'-sulfinylbisbenzene; 2,4,5-tri-tert-butylpyrimidine; tri-n-butyl-tin hydride; trifluoromethylsulfonic anhydride; In dichloromethane; toluene;
DOI:10.1021/jo0526688