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

Base Information

• Chemical Name: phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(2-naphthylmethyl)-β-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside
• CAS No.: 951025-09-5
• Molecular Formula: C₄₉H₄₆O₁₀S
• Molecular Weight: 826.964

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 5 articles about phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(2-naphthylmethyl)-β-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-2-O-(prop-2-ynyl)-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:

phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside (855306-33-1) + phenyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside (951025-07-3) → phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(2-naphthylmethyl)-α-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside + phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(2-naphthylmethyl)-β-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside (951025-09-5)

Guidance literature:

phenyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside; With trifluoromethylsulfonic anhydride; sulfobromophthalein sodium; 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; Further stages.;

DOI:10.1021/jo071009n

Reference yield:

phenyl 4,6-O-benzylidene-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside (951025-06-2) → phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(2-naphthylmethyl)-β-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside (951025-09-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 91 percent / NaH / dimethylformamide; various solvent(s) / 3 h / 0 °C

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

3.1: BSP; TTBP; Tf₂O / CH₂Cl₂ / 0.5 h / -60 °C

3.2: CH₂Cl₂ / 2 h / -78 °C

With trifluoromethylsulfonic anhydride; sodium hydride; sulfobromophthalein sodium; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/jo071009n

Reference yield:

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-19-9) → phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(2-naphthylmethyl)-β-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside (951025-09-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: Bu₂SnO / toluene / 4 h / Heating

1.2: 94 percent / CsF / dimethylformamide / 6 h / 95 °C

2.1: 91 percent / NaH / dimethylformamide; various solvent(s) / 3 h / 0 °C

3.1: 93 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 20 °C

4.1: BSP; TTBP; Tf₂O / CH₂Cl₂ / 0.5 h / -60 °C

4.2: CH₂Cl₂ / 2 h / -78 °C

With trifluoromethylsulfonic anhydride; sodium hydride; di(n-butyl)tin oxide; sulfobromophthalein sodium; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo071009n

upstream raw materials:

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

phenyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside

phenyl 4,6-O-benzylidene-3-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside

2-bromomethylnaphthyl bromide

Downstream raw materials:

methyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(2-naphthylmethyl)-β-D-mannopyranosyl-(1->3)-4,6-O-benzylidene-2-O-(prop-2-ynyl)-β-D-mannopyranosyl-(1->3)-4,6-benzylidene-2-O-(prop-2-ynyl)-β-D-mannopyranoside

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

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