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

Base Information

Chemical Name:phenyl 4-O-benzyl-3-O-tert-butyldimethylsilyl-2-O-(2-naphthylmethyl)-1-thio-α-D-mannopyranoside
CAS No.:1607005-86-6
Molecular Formula:C₃₆H₄₄O₅SSi
Molecular Weight:616.894
Hs Code.:

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

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

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

There total 7 articles about phenyl 4-O-benzyl-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: 89.0%

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

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

Guidance literature:: With borane-THF; trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; at 23 ℃; for 3h; regioselective reaction; Inert atmosphere;
DOI:10.1021/jo500640n

Reference yield: 30.0%

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

: 1607006-36-9
C₃₀H₃₀O₅S

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

Guidance literature:: With borane-THF; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; dichloromethane; at 23 ℃; for 21h; Temperature; Time; Reagent/catalyst; regioselective reaction; Inert atmosphere;
DOI:10.1021/jo500640n

Reference yield:

: 69739-34-0
t-butyldimethylsiyl triflate

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

Guidance literature:: Multi-step reaction with 3 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

With borane-THF; sodium hydride; triethylamine; scandium tris(trifluoromethanesulfonate); In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1021/jo500640n