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

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Chemical Name:phenyl 4,6-O-benzylidene-2-O-benzyl-3-O-(2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-1-thio-α-D-mannopyranoside
CAS No.:808762-10-9
Molecular Formula:C₅₃H₅₄O₁₀S
Molecular Weight:883.072
Hs Code.:

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

There total 8 articles about phenyl 4,6-O-benzylidene-2-O-benzyl-3-O-(2,3,6-tri-O-benzyl-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: 82.0%

: 100-39-0
benzyl bromide

: 808762-09-6
phenyl 4,6-O-benzylidene-2-O-benzyl-3-O-(2,3-di-O-benzyl-β-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

: 808762-10-9
phenyl 4,6-O-benzylidene-2-O-benzyl-3-O-(2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

Guidance literature:: phenyl 4,6-O-benzylidene-2-O-benzyl-3-O-(2,3-di-O-benzyl-β-D-mannopyranosyl)-1-thio-α-D-mannopyranoside; With di(n-butyl)tin oxide; In toluene; for 3h; Heating;

benzyl bromide; With cesium fluoride; In toluene; for 24h; Heating;
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

: 808762-10-9
phenyl 4,6-O-benzylidene-2-O-benzyl-3-O-(2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 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

4.1: 92 percent / aq. AcOH / CH₂Cl₂ / 0.67 h / 20 °C

5.1: Bu₂SnO / toluene / 3 h / Heating

5.2: 82 percent / CsF / toluene / 24 h / Heating

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

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 808762-10-9
phenyl 4,6-O-benzylidene-2-O-benzyl-3-O-(2,3,6-tri-O-benzyl-β-D-mannopyranosyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 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

4.1: 92 percent / aq. AcOH / CH₂Cl₂ / 0.67 h / 20 °C

5.1: Bu₂SnO / toluene / 3 h / Heating

5.2: 82 percent / CsF / toluene / 24 h / Heating

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