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

Base Information

Chemical Name:S-ethyl 2,3-di-O-benzyl-4,6-O-(α-methoxycarbonyl)ethylidene-1-thio-α-D-mannopyranoside
CAS No.:887700-26-7
Molecular Formula:C₂₆H₃₂O₇S
Molecular Weight:488.602
Hs Code.:

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

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

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

There total 1 articles about S-ethyl 2,3-di-O-benzyl-4,6-O-(α-methoxycarbonyl)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: 20.0%

: 600-22-6
pyruvic acid methyl ester

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

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

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

Guidance literature:: With boron trifluoride diethyl etherate; In acetonitrile; at 20 ℃; for 4h;
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

: methyl 4-O-(2,3-di-O-benzyl-4,6-O-ethylidene-β-D-mannopyranosyl)-2,3-O-isopropylidene-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 3 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

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

3.2: 15 percent / NaOMe / methanol / 1 h / 20 °C

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