p-methylphenyl 6-O-(2,4-di-O-benzyl-3,6-di-O-propargyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-3-O-propargyl-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:p-methylphenyl 6-O-(2,4-di-O-benzyl-3,6-di-O-propargyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-3-O-propargyl-1-thio-α-D-mannopyranoside
CAS No.:1369224-14-5
Molecular Formula:C₅₆H₅₈O₁₀S
Molecular Weight:923.137
Hs Code.:

Synonyms:p-methylphenyl 6-O-(2,4-di-O-benzyl-3,6-di-O-propargyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-3-O-propargyl-1-thio-α-D-mannopyranoside

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Chemical Property of p-methylphenyl 6-O-(2,4-di-O-benzyl-3,6-di-O-propargyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-3-O-propargyl-1-thio-α-D-mannopyranoside

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Technology Process of p-methylphenyl 6-O-(2,4-di-O-benzyl-3,6-di-O-propargyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-3-O-propargyl-1-thio-α-D-mannopyranoside

There total 7 articles about p-methylphenyl 6-O-(2,4-di-O-benzyl-3,6-di-O-propargyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-3-O-propargyl-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: 96.0%

: 1369224-27-0
p-methylphenyl 6-O-(2,4-di-O-benzyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-1-thio-α-D-mannopyranoside

: 106-96-7
propargyl bromide

: 1369224-14-5
p-methylphenyl 6-O-(2,4-di-O-benzyl-3,6-di-O-propargyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-3-O-propargyl-1-thio-α-D-mannopyranoside

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 2.5h;
DOI:10.1039/c2cc30773a

Reference yield:

: 950602-62-7
p-methylphenyl 2-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

: 1369224-14-5
p-methylphenyl 6-O-(2,4-di-O-benzyl-3,6-di-O-propargyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-3-O-propargyl-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: pyridine / 0.5 h / 0 - 20 °C

2.1: borane-THF; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 4 h / 0 °C

3.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.75 h / -80 °C / Inert atmosphere

4.1: sodium methylate / methanol / 15 h / 20 °C

4.2: Amberlite^.(R). IR₁₂₀ H⁺ resin

5.1: sodium hydride / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C

With pyridine; borane-THF; trimethylsilyl trifluoromethanesulfonate; di-n-butylboryl trifluoromethanesulfonate; sodium methylate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/c2cc30773a

Reference yield:

: 1369224-21-4
p-methylphenyl 3-O-benzoyl-2-O-benzyl-4,6-O-benzylidene-1-thio-α-D-mannopyranoside

: 1369224-14-5
p-methylphenyl 6-O-(2,4-di-O-benzyl-3,6-di-O-propargyl-α-D-mannopyranosyl)-2,4-di-O-benzyl-3-O-propargyl-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: borane-THF; di-n-butylboryl trifluoromethanesulfonate / dichloromethane / 4 h / 0 °C

2.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.75 h / -80 °C / Inert atmosphere

3.1: sodium methylate / methanol / 15 h / 20 °C

3.2: Amberlite^.(R). IR₁₂₀ H⁺ resin

4.1: sodium hydride / N,N-dimethyl-formamide / 2.5 h / 0 - 20 °C

With borane-THF; trimethylsilyl trifluoromethanesulfonate; di-n-butylboryl trifluoromethanesulfonate; sodium methylate; sodium hydride; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1039/c2cc30773a