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

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Chemical Name:phenyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside
CAS No.:1250346-19-0
Molecular Formula:C₃₆H₄₂O₅SSi
Molecular Weight:614.878
Hs Code.:

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

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

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

There total 4 articles about phenyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-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: 96.0%

: 1250346-03-2
phenyl 4,6-O-benzylidene-2-O-(2-methylnaphthyl)-1-thio-α-D-mannopyranoside

: 18162-48-6
tert-butyldimethylsilyl chloride

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

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 16h;
DOI:10.1021/ol101951u

Reference yield:

: 922183-00-4
phenyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside

: 939-26-4
2-bromomethylnaphthyl bromide

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

Guidance literature:: phenyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; for 0.333333h; Cooling with ice; Inert atmosphere;

2-bromomethylnaphthyl bromide; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 3h; regioselective reaction; Inert atmosphere;
DOI:10.1021/jo500640n

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

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

Guidance literature:: Multi-step reaction with 2 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

With sodium hydride; triethylamine; In N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/jo500640n