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

Base Information

Chemical Name:S-ethyl 2-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside
CAS No.:733002-00-1
Molecular Formula:C₄₂H₄₁IO₆S₂
Molecular Weight:832.82
Hs Code.:

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

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Chemical Property of S-ethyl 2-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

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Technology Process of S-ethyl 2-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

There total 6 articles about S-ethyl 2-O-benzyl-4,6-O-[α-2-(2-iodophenyl)ethylthiocarbonyl]benzylidene-3-O-(2-naphthalenylmethyl)-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: 82.0%

: 177748-62-8
2-(2-iodophenyl)-1-ethanethiol

: 733001-99-5
S-ethyl 2-O-benzyl-4,6-O-(α-methoxycarbonyl)benzylidene-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside

: 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

Guidance literature:: 2-(2-iodophenyl)-1-ethanethiol; With trimethylaluminum; In hexane; toluene; at 0 ℃; for 0.5h;

S-ethyl 2-O-benzyl-4,6-O-(α-methoxycarbonyl)benzylidene-3-O-(2-naphthalenylmethyl)-1-thio-α-D-mannopyranoside; In hexane; toluene; for 4h; Heating;
DOI:10.1021/ja048070j

Reference yield:

: 100-39-0
benzyl bromide

: 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

Guidance literature:: Multi-step reaction with 4 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

With 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:

: 142924-31-0
S-ethyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

: 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

Guidance literature:: Multi-step reaction with 5 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

With 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