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

Base Information

Chemical Name:phenyl 4-O-benzyl-3-O-tert-butyldimethylsilyl-6-cyano-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside
CAS No.:1607005-93-5
Molecular Formula:C₃₇H₄₃NO₄SSi
Molecular Weight:625.904
Hs Code.:

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

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Chemical Property of phenyl 4-O-benzyl-3-O-tert-butyldimethylsilyl-6-cyano-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside

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Technology Process of phenyl 4-O-benzyl-3-O-tert-butyldimethylsilyl-6-cyano-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside

There total 6 articles about phenyl 4-O-benzyl-3-O-tert-butyldimethylsilyl-6-cyano-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: 88.0%

: potassium cyanide

: 1607005-90-2
phenyl 4-O-benzyl-3-O-tert-butyldimethylsilyl-2-O-(2-naphthylmethyl)-1-thio-6-O-tosyl-α-D-mannopyranoside

: 1607005-93-5
phenyl 4-O-benzyl-3-O-tert-butyldimethylsilyl-6-cyano-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside

Guidance literature:: With 18-crown-6 ether; In acetonitrile; at 0.22 - 20 ℃; for 24.5h; Molecular sieve; 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

: 1607005-93-5
phenyl 4-O-benzyl-3-O-tert-butyldimethylsilyl-6-cyano-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

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

2: pyridine; dmap / 20 h / 0 °C / Inert atmosphere

3: 18-crown-6 ether / acetonitrile / 24.5 h / 0.22 - 20 °C / Molecular sieve; Inert atmosphere

With pyridine; dmap; borane-THF; 18-crown-6 ether; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1021/jo500640n

Reference yield:

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

: 1607005-93-5
phenyl 4-O-benzyl-3-O-tert-butyldimethylsilyl-6-cyano-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 5 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; scandium tris(trifluoromethanesulfonate) / tetrahydrofuran; dichloromethane / 21 h / 23 °C / Inert atmosphere

4.1: pyridine; dmap / 20 h / 0 °C / Inert atmosphere

5.1: 18-crown-6 ether / acetonitrile / 24.5 h / 0.22 - 20 °C / Molecular sieve; Inert atmosphere

With pyridine; dmap; borane-THF; 18-crown-6 ether; sodium hydride; triethylamine; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; mineral oil;
DOI:10.1021/jo500640n