methyl 3,6-di-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-4-O-triisopropylsilyl-α-D-mannopyranoside

Base Information

Chemical Name:methyl 3,6-di-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-4-O-triisopropylsilyl-α-D-mannopyranoside
CAS No.:1350309-45-3
Molecular Formula:C₄₁H₅₄O₅SSi
Molecular Weight:687.028
Hs Code.:

Synonyms:methyl 3,6-di-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-4-O-triisopropylsilyl-α-D-mannopyranoside

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Chemical Property of methyl 3,6-di-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-4-O-triisopropylsilyl-α-D-mannopyranoside

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Technology Process of methyl 3,6-di-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-4-O-triisopropylsilyl-α-D-mannopyranoside

There total 8 articles about methyl 3,6-di-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-4-O-triisopropylsilyl-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: 85.0%

: 1350309-56-6
methyl 3,6-di-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 1350309-45-3
methyl 3,6-di-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-4-O-triisopropylsilyl-α-D-mannopyranoside

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 - 20 ℃; for 24h; Inert atmosphere;
DOI:10.1021/ja208528c

Reference yield:

: 1350309-53-3
methyl 4,6-O-benzylidene-2-O-(2-naphthylmethyl)-1-thio-3-O-triisopropylsilyl-α-D-mannopyranoside

: 1350309-45-3
methyl 3,6-di-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-4-O-triisopropylsilyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 0 - 20 °C / Inert atmosphere

2: sodium hydride / N,N-dimethyl-formamide / 3 h / 0 - 20 °C / Inert atmosphere

3: triethylsilane; trifluoroacetic acid / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere

4: 2,6-dimethylpyridine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; triethylsilane; tetrabutyl ammonium fluoride; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja208528c

Reference yield:

: 1350309-52-2
methyl 4,6-O-benzylidene-1-thio-3-O-triisopropylsilyl-α-D-mannopyranoside

: 1350309-45-3
methyl 3,6-di-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-4-O-triisopropylsilyl-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1: sodium hydride / N,N-dimethyl-formamide / 3 h / 0 - 20 °C / Inert atmosphere

2: tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 0 - 20 °C / Inert atmosphere

3: sodium hydride / N,N-dimethyl-formamide / 3 h / 0 - 20 °C / Inert atmosphere

4: triethylsilane; trifluoroacetic acid / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere

5: 2,6-dimethylpyridine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

With 2,6-dimethylpyridine; triethylsilane; tetrabutyl ammonium fluoride; sodium hydride; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/ja208528c