methyl (phenyl 2,3-diazido-4-O-tert-butyldimethylsilyl-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)

Base Information

Chemical Name:methyl (phenyl 2,3-diazido-4-O-tert-butyldimethylsilyl-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)
CAS No.:1319717-49-1
Molecular Formula:C₁₉H₂₈N₆O₄SSi
Molecular Weight:464.621
Hs Code.:

Synonyms:methyl (phenyl 2,3-diazido-4-O-tert-butyldimethylsilyl-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)

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Chemical Property of methyl (phenyl 2,3-diazido-4-O-tert-butyldimethylsilyl-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)

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Technology Process of methyl (phenyl 2,3-diazido-4-O-tert-butyldimethylsilyl-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)

There total 6 articles about methyl (phenyl 2,3-diazido-4-O-tert-butyldimethylsilyl-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate) 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%

: 1319717-07-1
methyl (phenyl 2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)

: 69739-34-0
t-butyldimethylsiyl triflate

: 1319717-49-1
methyl (phenyl 2,3-diazido-4-O-tert-butyldimethylsilyl-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)

Guidance literature:: With triethylamine; In dichloromethane; at 0 - 20 ℃;
DOI:10.1021/jo201179p

Reference yield:

: 1319717-03-7
phenyl 2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranoside

: 1319717-49-1
methyl (phenyl 2,3-diazido-4-O-tert-butyldimethylsilyl-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)

Guidance literature:: Multi-step reaction with 3 steps

1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; ethyl acetate / 1 h / 0 - 20 °C

2: potassium carbonate / N,N-dimethyl-formamide / 20 °C

3: triethylamine / dichloromethane / 0 - 20 °C

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; potassium carbonate; triethylamine; In dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo201179p

Reference yield:

: 1319717-00-4
phenyl 4,6-di-O-acetyl-2,3-diazido-2,3-dideoxy-1-thio-β-D-mannopyranoside

: 1319717-49-1
methyl (phenyl 2,3-diazido-4-O-tert-butyldimethylsilyl-2,3-dideoxy-1-thio-β-D-mannopyranosyl uronate)

Guidance literature:: Multi-step reaction with 4 steps

1.1: sodium methylate / methanol / 1.5 h

1.2: Amberlite-H⁺

2.1: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / water; ethyl acetate / 1 h / 0 - 20 °C

3.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C

4.1: triethylamine / dichloromethane / 0 - 20 °C

With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; sodium methylate; potassium carbonate; triethylamine; In methanol; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo201179p