methyl 2,3,6-tri-O-benzyl-4-O-{2-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranosyl}-β-D-glucopyranoside

Base Information

Chemical Name:methyl 2,3,6-tri-O-benzyl-4-O-{2-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranosyl}-β-D-glucopyranoside
CAS No.:733002-02-3
Molecular Formula:C₆₈H₆₇IO₁₂S
Molecular Weight:1235.24
Hs Code.:

methyl 2,3,6-tri-O-benzyl-4-O-{2-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranosyl}-β-D-glucopyranoside

Synonyms:methyl 2,3,6-tri-O-benzyl-4-O-{2-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranosyl}-β-D-glucopyranoside

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Chemical Property of methyl 2,3,6-tri-O-benzyl-4-O-{2-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranosyl}-β-D-glucopyranoside

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Technology Process of methyl 2,3,6-tri-O-benzyl-4-O-{2-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranosyl}-β-D-glucopyranoside

There total 8 articles about methyl 2,3,6-tri-O-benzyl-4-O-{2-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranosyl}-β-D-glucopyranoside 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%

: 19488-49-4
methyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside

: 733002-00-1
S-ethyl 2-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

: 733002-02-3
methyl 2,3,6-tri-O-benzyl-4-O-{2-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranosyl}-β-D-glucopyranoside

: methyl 2,3,6-tri-O-benzyl-4-O-{2-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-3-O-(2-naphthalenylmethyl)-α-D-mannopyranosyl}-β-D-glucopyranoside

Guidance literature:: S-ethyl 2-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside; With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpiperidine; In dichloromethane; at -60 ℃; for 0.166667h;

methyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside; In dichloromethane; at -60 - 20 ℃;
DOI:10.1021/ja048070j

Reference yield:

: 100-39-0
benzyl bromide

: 733002-02-3
methyl 2,3,6-tri-O-benzyl-4-O-{2-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranosyl}-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH / tetrahydrofuran / 0.5 h

1.2: 43.5 g / tetrahydrofuran

2.1: 97 percent / neo-pentyl glycol; CSA / CH₂Cl₂ / 20 °C

3.1: 43 percent / CSA / acetonitrile / 13 h / Heating

4.1: Me₃Al / toluene; hexane / 0.5 h / 0 °C

4.2: 82 percent / toluene; hexane / 4 h / Heating

5.1: 1-benzenesulfinylpiperidine; 2,4,6-tri-tert-butylpiperidine; triflic anhydride / CH₂Cl₂ / 0.17 h / -60 °C

5.2: 85 percent / CH₂Cl₂ / -60 - 20 °C

With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpiperidine; camphor-10-sulfonic acid; trimethylaluminum; sodium hydride; 2,2-Dimethyl-1,3-propanediol; In tetrahydrofuran; hexane; dichloromethane; toluene; acetonitrile;
DOI:10.1021/ja048070j

Reference yield:

: 939-26-4
2-bromomethylnaphthyl bromide

: 733002-02-3
methyl 2,3,6-tri-O-benzyl-4-O-{2-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-3-O-(2-naphthalenylmethyl)-β-D-mannopyranosyl}-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1.1: Bu₂SnO / toluene / 4 h / Heating

1.2: dimethylformamide / 6 h / 95 °C

2.1: NaH / tetrahydrofuran / 0.5 h

2.2: 43.5 g / tetrahydrofuran

3.1: 97 percent / neo-pentyl glycol; CSA / CH₂Cl₂ / 20 °C

4.1: 43 percent / CSA / acetonitrile / 13 h / Heating

5.1: Me₃Al / toluene; hexane / 0.5 h / 0 °C

5.2: 82 percent / toluene; hexane / 4 h / Heating

6.1: 1-benzenesulfinylpiperidine; 2,4,6-tri-tert-butylpiperidine; triflic anhydride / CH₂Cl₂ / 0.17 h / -60 °C

6.2: 85 percent / CH₂Cl₂ / -60 - 20 °C

With 1-benzenesulfinyl piperidine; trifluoromethylsulfonic anhydride; 2,4,6-tri-tert-butylpiperidine; camphor-10-sulfonic acid; trimethylaluminum; sodium hydride; di(n-butyl)tin oxide; 2,2-Dimethyl-1,3-propanediol; In tetrahydrofuran; hexane; dichloromethane; toluene; acetonitrile;
DOI:10.1021/ja048070j