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

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Chemical Name:phenyl 4,6-O-benzylidene-2-O-benzyl-3-O-(2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-β-D-mannopyranosyl)-1-thio-α-D-mannopyranoside
CAS No.:808762-08-5
Molecular Formula:C₅₄H₅₄O₁₁S
Molecular Weight:911.082
Hs Code.:

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

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

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

There total 6 articles about phenyl 4,6-O-benzylidene-2-O-benzyl-3-O-(2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-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: 62.0%

: 158716-08-6
phenyl 4,6-O-benzylidene-2-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside

: 808762-01-8
phenyl 2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-1-thio-α-D-mannopyranoside

: 808762-08-5
phenyl 4,6-O-benzylidene-2-O-benzyl-3-O-(2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-β-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

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

phenyl 4,6-O-benzylidene-2-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside; With trifluoromethylsulfonic anhydride; In dichloromethane; at -60 ℃; for 3h;
DOI:10.1021/ja0471931

Reference yield:

: 2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-63-1,105088-17-3,149495-84-1,77481-62-0
(2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

: 808762-08-5
phenyl 4,6-O-benzylidene-2-O-benzyl-3-O-(2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-β-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 57 percent / p-TsOH / dimethylformamide / 2 h / 60 °C

2.1: 75 percent / tetrabutylammonium hydrogensulfate; aq. NaOH / CH₂Cl₂ / 20 h / Heating

3.1: 1-benzenesulfinylpiperidine; 2,4,6-tri-t-Bu-pyrimidine; 3A molecular sieves / CH₂Cl₂ / 0.5 h / -60 °C

3.2: 62 percent / Tf₂O / CH₂Cl₂ / 3 h / -60 °C

With sodium hydroxide; 1-benzenesulfinyl piperidine; 3 A molecular sieve; tetra(n-butyl)ammonium hydrogensulfate; toluene-4-sulfonic acid; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja0471931

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 808762-08-5
phenyl 4,6-O-benzylidene-2-O-benzyl-3-O-(2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-β-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 57 percent / p-TsOH / dimethylformamide / 2 h / 60 °C

2.1: 75 percent / tetrabutylammonium hydrogensulfate; aq. NaOH / CH₂Cl₂ / 20 h / Heating

3.1: 1-benzenesulfinylpiperidine; 2,4,6-tri-t-Bu-pyrimidine; 3A molecular sieves / CH₂Cl₂ / 0.5 h / -60 °C

3.2: 62 percent / Tf₂O / CH₂Cl₂ / 3 h / -60 °C

With sodium hydroxide; 1-benzenesulfinyl piperidine; 3 A molecular sieve; tetra(n-butyl)ammonium hydrogensulfate; toluene-4-sulfonic acid; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja0471931