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

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Chemical Name:phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(tert-butyldimethylsilyl)-1-thio-α-D-mannopyranoside
CAS No.:855306-34-2
Molecular Formula:C₂₈H₃₆O₅SSi
Molecular Weight:512.742
Hs Code.:

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

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

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

There total 3 articles about phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(tert-butyldimethylsilyl)-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: 92.0%

: 855306-33-1
phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-1-thio-α-D-mannopyranoside

: 18162-48-6
tert-butyldimethylsilyl chloride

: 855306-34-2
phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(tert-butyldimethylsilyl)-1-thio-α-D-mannopyranoside

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 12h;
DOI:10.1021/ol050680g DOI:10.1021/jo0526789

Reference yield:

: 168138-26-9
phenyl 4,6-O-benzylidene-3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside

: 855306-34-2
phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(tert-butyldimethylsilyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 85 percent / NaH / dimethylformamide; various solvent(s) / 3 h

2: 93 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 20 °C

3: 92 percent / imidazole / dimethylformamide / 12 h / 20 °C

With 1H-imidazole; sodium hydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jo0526789

Reference yield:

: 855306-32-0
phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside

: 855306-34-2
phenyl 4,6-O-benzylidene-2-O-(prop-2-ynyl)-3-O-(tert-butyldimethylsilyl)-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 93 percent / DDQ / CH₂Cl₂; H₂O / 3 h / 20 °C

2: 92 percent / imidazole / dimethylformamide / 12 h / 20 °C

With 1H-imidazole; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/ol050680g DOI:10.1021/jo0526789