phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

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Chemical Name:phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-1-thio-α-D-mannopyranoside
CAS No.:855306-48-8
Molecular Formula:C₄₉H₄₈O₁₀S
Molecular Weight:828.98
Hs Code.:

Synonyms:phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

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Chemical Property of phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

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Technology Process of phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

There total 3 articles about phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-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: 83.0%

: 855306-33-1
phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside

: 159407-17-7
phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

: 855306-48-8
phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

: phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

Guidance literature:: phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside; With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpyrimidine; 4 A molecular sieve; In dichloromethane; at -60 ℃; for 0.5h;

phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside; In dichloromethane; at -78 ℃; for 2h;

With triethyl phosphite; In dichloromethane; at -78 - 20 ℃;
DOI:10.1021/ol050680g

Reference yield:

: 855306-32-0
phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside

: 855306-48-8
phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: 93 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 20 °C

2.1: 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine; trifluoromethanesulfonic anhydride / CH₂Cl₂ / 0.5 h / -60 °C

2.2: 83 percent / triethylphosphite / CH₂Cl₂ / -78 °C

With 1-benzenesulfinyl piperidine; trifluoromethanesulfonic acid anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; water;
DOI:10.1021/jo0526789

Reference yield:

: 168138-26-9
phenyl 4,6-O-benzylidene-3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside

: 855306-48-8
phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 85 percent / NaH / dimethylformamide; various solvent(s) / 3 h

2.1: 93 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 20 °C

3.1: 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine; trifluoromethanesulfonic anhydride / CH₂Cl₂ / 0.5 h / -60 °C

3.2: 83 percent / triethylphosphite / CH₂Cl₂ / -78 °C

With 1-benzenesulfinyl piperidine; sodium hydride; trifluoromethanesulfonic acid anhydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo0526789