phenyl 3,6-anhydro-4-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside

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Chemical Name:phenyl 3,6-anhydro-4-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside
CAS No.:1607005-89-9
Molecular Formula:C₃₀H₂₈O₄S
Molecular Weight:484.616
Hs Code.:

Synonyms:phenyl 3,6-anhydro-4-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside

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Chemical Property of phenyl 3,6-anhydro-4-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside

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Technology Process of phenyl 3,6-anhydro-4-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside

There total 4 articles about phenyl 3,6-anhydro-4-O-benzyl-2-O-(2-naphthylmethyl)-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: 62.0%

: 1607005-86-6
phenyl 4-O-benzyl-3-O-tert-butyldimethylsilyl-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside

: 1607005-89-9
phenyl 3,6-anhydro-4-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside

Guidance literature:: With trifluoromethylsulfonic anhydride; In 1,2-dichloro-ethane; at -10 ℃; for 1h; Inert atmosphere;
DOI:10.1021/jo500640n

Reference yield:

: 1250346-19-0
phenyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside

: 1607005-89-9
phenyl 3,6-anhydro-4-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: borane-THF; trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran; dichloromethane / 3 h / 23 °C / Inert atmosphere

2: trifluoromethylsulfonic anhydride / 1,2-dichloro-ethane / 1 h / -10 °C / Inert atmosphere

With borane-THF; trifluoromethylsulfonic anhydride; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane;
DOI:10.1021/jo500640n

Reference yield:

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

: 1607005-89-9
phenyl 3,6-anhydro-4-O-benzyl-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: triethylamine / N,N-dimethyl-formamide / 2 h / -10 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.33 h / Cooling with ice; Inert atmosphere

2.2: 3 h / 20 °C / Inert atmosphere

3.1: borane-THF; trimethylsilyl trifluoromethanesulfonate / tetrahydrofuran; dichloromethane / 3 h / 23 °C / Inert atmosphere

4.1: trifluoromethylsulfonic anhydride / 1,2-dichloro-ethane / 1 h / -10 °C / Inert atmosphere

With borane-THF; trifluoromethylsulfonic anhydride; trimethylsilyl trifluoromethanesulfonate; sodium hydride; triethylamine; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/jo500640n