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

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Chemical Name:phenyl 4,6-O-benzylidene-3-O-tert-butyldimethylsilyl-1-thio-α-D-mannopyranoside
CAS No.:922183-00-4
Molecular Formula:C₂₅H₃₄O₅SSi
Molecular Weight:474.693
Hs Code.:

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

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

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

There total 6 articles about phenyl 4,6-O-benzylidene-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: 100.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

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

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

Guidance literature:: phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside; With di(n-butyl)tin oxide; In toluene; at 110 ℃; for 2h;

tert-butyldimethylsilyl chloride; With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; for 12h; Further stages.;
DOI:10.1002/anie.200602699

Reference yield:

: 2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-63-1,105088-17-3,149495-84-1,77481-62-0
(2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

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

Guidance literature:: Multi-step reaction with 2 steps

1.1: camphor-10-sulfonic acid / N,N-dimethyl-formamide / 50 °C / 76.01 Torr

2.1: di(n-butyl)tin oxide / toluene / 2 h / 110 °C / Inert atmosphere

2.2: 12 h / 20 °C / Inert atmosphere

With camphor-10-sulfonic acid; di(n-butyl)tin oxide; In N,N-dimethyl-formamide; toluene;
DOI:10.1002/chem.201203725

Reference yield:

: 13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,121524-01-4,121570-34-1,108032-93-5
phenyl 2,3,4,6-tetra-O-acetyl-1-thio-α-D-mannopyranoside

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

Guidance literature:: Multi-step reaction with 3 steps

1: sodium methylate / 4 h / 20 °C / Inert atmosphere

2: camphor-10-sulfonic acid / acetonitrile / 20 °C / Inert atmosphere

3: 1H-imidazole / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

With 1H-imidazole; camphor-10-sulfonic acid; sodium methylate; In N,N-dimethyl-formamide; acetonitrile;
DOI:10.1002/anie.202000231