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

Base Information

Chemical Name:methyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1-3)-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1-4)-2,3,6-tri-O-benzyl-β-D-mannopyranoside
CAS No.:351060-25-8
Molecular Formula:C₇₅H₈₀O₁₆
Molecular Weight:1237.45
Hs Code.:

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

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Chemical Property of methyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1-3)-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1-4)-2,3,6-tri-O-benzyl-β-D-mannopyranoside

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Technology Process of methyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1-3)-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1-4)-2,3,6-tri-O-benzyl-β-D-mannopyranoside

There total 17 articles about methyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1-3)-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1-4)-2,3,6-tri-O-benzyl-β-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: 87.0%

: 100-39-0
benzyl bromide

: 351060-24-7
methyl 2,3-di-O-benzyl-β-D-mannopyranosyl-(1-3)-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1-4)-2,3,6-tri-O-benzyl-β-D-mannopyranoside

: 351060-25-8
methyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1-3)-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1-4)-2,3,6-tri-O-benzyl-β-D-mannopyranoside

Guidance literature:: methyl 2,3-di-O-benzyl-β-D-mannopyranosyl-(1-3)-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1-4)-2,3,6-tri-O-benzyl-β-D-mannopyranoside; With sodium hydride; In tetrahydrofuran; at 20 ℃; for 0.5h;

benzyl bromide; In tetrahydrofuran; Heating;
DOI:10.1021/ja0471931

Reference yield:

: 351060-20-3
methyl 2,3,6-tri-O-benzyl-β-D-mannopyranoside

: 351060-25-8
methyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1-3)-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1-4)-2,3,6-tri-O-benzyl-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: 2,4,6-tri-t-Bu-pyrimidine / CH₂Cl₂ / 0.5 h / -78 °C

1.2: 81 percent / Tf₂O / CH₂Cl₂ / 1 h / -78 °C

2.1: 83 percent / DDQ; H₂O / CH₂Cl₂ / 0.5 h / 20 °C

3.1: 2,4,6-tri-t-Bu-pyrimidine / CH₂Cl₂ / 0.5 h / -78 °C

3.2: 72 percent / Tf₂O / CH₂Cl₂ / 1 h / -78 °C

4.1: 70 percent / aq. AcOH / 1 h / 20 °C

5.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

5.2: 87 percent / tetrahydrofuran / Heating

With water; sodium hydride; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja0471931

Reference yield:

: 351060-18-9
methyl 2,3-di-O-benzyl-4,6-O-p-methoxybenzylidene-β-D-mannopyranoside

: 351060-25-8
methyl 2,3,6-tri-O-benzyl-β-D-mannopyranosyl-(1-3)-2-O-benzyl-4,6-O-benzylidene-β-D-mannopyranosyl-(1-4)-2,3,6-tri-O-benzyl-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 7 steps

1.1: 97 percent / aq. AcOH / CH₂Cl₂ / 1 h / 20 °C

2.1: Bu₂SnO / toluene / 3 h / Heating

2.2: 87 percent / CsF / toluene / 24 h / Heating

3.1: 2,4,6-tri-t-Bu-pyrimidine / CH₂Cl₂ / 0.5 h / -78 °C

3.2: 81 percent / Tf₂O / CH₂Cl₂ / 1 h / -78 °C

4.1: 83 percent / DDQ; H₂O / CH₂Cl₂ / 0.5 h / 20 °C

5.1: 2,4,6-tri-t-Bu-pyrimidine / CH₂Cl₂ / 0.5 h / -78 °C

5.2: 72 percent / Tf₂O / CH₂Cl₂ / 1 h / -78 °C

6.1: 70 percent / aq. AcOH / 1 h / 20 °C

7.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

7.2: 87 percent / tetrahydrofuran / Heating

With water; sodium hydride; di(n-butyl)tin oxide; acetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,4,6-tri-tert-butylpyrimidine; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ja0471931