4,6-O-benzylidene-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-deoxy-1-(2-oxo-2-phenylethyl)-β-D-mannopyranose

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Chemical Name:4,6-O-benzylidene-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-deoxy-1-(2-oxo-2-phenylethyl)-β-D-mannopyranose
CAS No.:1257634-76-6
Molecular Formula:C₃₄H₄₂O₆Si
Molecular Weight:574.789
Hs Code.:

Synonyms:4,6-O-benzylidene-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-deoxy-1-(2-oxo-2-phenylethyl)-β-D-mannopyranose

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Chemical Property of 4,6-O-benzylidene-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-deoxy-1-(2-oxo-2-phenylethyl)-β-D-mannopyranose

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Technology Process of 4,6-O-benzylidene-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-deoxy-1-(2-oxo-2-phenylethyl)-β-D-mannopyranose

There total 7 articles about 4,6-O-benzylidene-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-deoxy-1-(2-oxo-2-phenylethyl)-β-D-mannopyranose 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: 81.0%

: 13735-81-4
1-styrenyloxytrimethylsilane

: 1257634-63-1
phenyl 4,6-O-benzylidene-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-deoxy-1-thio-α-D-mannopyranoside

: 1257634-76-6
4,6-O-benzylidene-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-deoxy-1-(2-oxo-2-phenylethyl)-β-D-mannopyranose

Guidance literature:: phenyl 4,6-O-benzylidene-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-deoxy-1-thio-α-D-mannopyranoside; With trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -55 ℃; for 0.5h; Inert atmosphere; Molecular sieve;

1-styrenyloxytrimethylsilane; In dichloromethane; at -55 ℃; stereoselective reaction; Inert atmosphere; Molecular sieve;
DOI:10.1021/jo101453y

Reference yield:

: 158716-10-0
phenyl 3-O-acetyl-2-O-benzyl-4,6-O-benzylidene-1-deoxy-1-thio-α-D-mannopyranoside

: 1257634-76-6
4,6-O-benzylidene-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-deoxy-1-(2-oxo-2-phenylethyl)-β-D-mannopyranose

Guidance literature:: Multi-step reaction with 4 steps

1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 1.5 h / -78 - -20 °C

2.1: trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 0.5 h / -55 °C / Inert atmosphere; Molecular sieve

2.2: -55 °C / Inert atmosphere; Molecular sieve

3.1: sodium methylate / methanol / 0.5 h / 20 °C

4.1: 1H-imidazole / N,N-dimethyl-formamide / 12 h / 20 °C

With 1H-imidazole; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; sodium methylate; 3-chloro-benzenecarboperoxoic acid; 2,4,6-tri-tert-butylpyrimidine; In methanol; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo101453y

Reference yield:

: 158716-08-6
phenyl 4,6-O-benzylidene-2-O-benzyl-1-deoxy-1-thio-α-D-mannopyranoside

: 1257634-76-6
4,6-O-benzylidene-2-O-benzyl-3-O-tert-butyldimethylsilyl-1-deoxy-1-(2-oxo-2-phenylethyl)-β-D-mannopyranose

Guidance literature:: Multi-step reaction with 2 steps

1.1: 1H-imidazole / N,N-dimethyl-formamide / 14 h / 20 °C

2.1: trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine / dichloromethane / 0.5 h / -55 °C / Inert atmosphere; Molecular sieve

2.2: -55 °C / Inert atmosphere; Molecular sieve

With 1H-imidazole; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo101453y