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

Base Information

Chemical Name: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
CAS No.:887699-67-4
Molecular Formula:C₄₁H₄₉IO₁₁S
Molecular Weight:876.804
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 3 articles about 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 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: 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:

: 887700-26-7
S-ethyl 2,3-di-O-benzyl-4,6-O-(α-methoxycarbonyl)ethylidene-1-thio-α-D-mannopyranoside

: 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:: Multi-step reaction with 2 steps

1.1: 76 percent / AlMe₃ / hexane; toluene / 6 h / 20 °C

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

2.2: 80 percent / CH₂Cl₂ / 2 h / -70 °C

With molecular sieve; 1,1'-sulfinylbisbenzene; 2,4,5-tri-tert-butylpyrimidine; trimethylaluminum; trifluoromethylsulfonic anhydride; In hexane; dichloromethane; toluene;
DOI:10.1021/jo0526688

Reference yield:

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

: 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:: Multi-step reaction with 3 steps

1.1: 20 percent / BF₃*Et₂O / acetonitrile / 4 h / 20 °C

2.1: 76 percent / AlMe₃ / hexane; toluene / 6 h / 20 °C

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

3.2: 80 percent / CH₂Cl₂ / 2 h / -70 °C

With molecular sieve; 1,1'-sulfinylbisbenzene; 2,4,5-tri-tert-butylpyrimidine; boron trifluoride diethyl etherate; trimethylaluminum; trifluoromethylsulfonic anhydride; In hexane; dichloromethane; toluene; acetonitrile;
DOI:10.1021/jo0526688