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

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Chemical Name:methyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-2-O-(prop-2-ynyl)-β-D-mannopyranoside
CAS No.:951025-08-4
Molecular Formula:C₂₈H₂₈O₆
Molecular Weight:460.527
Hs Code.:

Synonyms:methyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-2-O-(prop-2-ynyl)-β-D-mannopyranoside

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Chemical Property of methyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-2-O-(prop-2-ynyl)-β-D-mannopyranoside

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Technology Process of methyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-2-O-(prop-2-ynyl)-β-D-mannopyranoside

There total 3 articles about methyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-2-O-(prop-2-ynyl)-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: 85.0%

: 67-56-1
methanol

: 951025-07-3
phenyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside

: 951025-08-4
methyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-2-O-(prop-2-ynyl)-β-D-mannopyranoside

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;

methanol; In dichloromethane; at -60 ℃; for 2h; Further stages.;
DOI:10.1021/jo071009n

Reference yield:

: 939-26-4
2-bromomethylnaphthyl bromide

: 951025-08-4
methyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-2-O-(prop-2-ynyl)-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 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: BSP; TTBP; Tf₂O / CH₂Cl₂ / 0.5 h / -60 °C

3.2: 85 percent / CH₂Cl₂ / 2 h / -60 °C

With trifluoromethylsulfonic anhydride; sodium hydride; di(n-butyl)tin oxide; sulfobromophthalein sodium; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo071009n

Reference yield:

: 159407-19-9
phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

: 951025-08-4
methyl 4,6-O-benzylidene-3-O-(2-naphthylmethyl)-2-O-(prop-2-ynyl)-β-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 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: BSP; TTBP; Tf₂O / CH₂Cl₂ / 0.5 h / -60 °C

3.2: 85 percent / CH₂Cl₂ / 2 h / -60 °C

With trifluoromethylsulfonic anhydride; sodium hydride; di(n-butyl)tin oxide; sulfobromophthalein sodium; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo071009n