S-phenyl 3,6-di-O-benzyl-2-O-(p-toluenesulfonyl)-4-O-(trimethylsilyl)-β-D-thiomannopyranoside

Base Information

Chemical Name:S-phenyl 3,6-di-O-benzyl-2-O-(p-toluenesulfonyl)-4-O-(trimethylsilyl)-β-D-thiomannopyranoside
CAS No.:848397-77-3
Molecular Formula:C₃₆H₄₂O₇S₂Si
Molecular Weight:678.943
Hs Code.:

Synonyms:S-phenyl 3,6-di-O-benzyl-2-O-(p-toluenesulfonyl)-4-O-(trimethylsilyl)-β-D-thiomannopyranoside

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Chemical Property of S-phenyl 3,6-di-O-benzyl-2-O-(p-toluenesulfonyl)-4-O-(trimethylsilyl)-β-D-thiomannopyranoside

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Technology Process of S-phenyl 3,6-di-O-benzyl-2-O-(p-toluenesulfonyl)-4-O-(trimethylsilyl)-β-D-thiomannopyranoside

There total 5 articles about S-phenyl 3,6-di-O-benzyl-2-O-(p-toluenesulfonyl)-4-O-(trimethylsilyl)-β-D-thiomannopyranoside 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: 95.0%

: 848397-76-2
S-phenyl 3,6-di-O-benzyl-2-O-(p-toluenesulfonyl)-β-D-thiomannopyranoside

: 27607-77-8
trimethylsilyl trifluoromethanesulfonate

: 848397-77-3
S-phenyl 3,6-di-O-benzyl-2-O-(p-toluenesulfonyl)-4-O-(trimethylsilyl)-β-D-thiomannopyranoside

Guidance literature:: With triethylamine; In dichloromethane; at -20 ℃; for 1h;
DOI:10.1016/j.tetasy.2004.11.032

Reference yield:

: 848397-74-0
phenyl 3-O-benzyl-4,6-O-benzylidene-1-thio-β-D-mannopyranoside

: 848397-77-3
S-phenyl 3,6-di-O-benzyl-2-O-(p-toluenesulfonyl)-4-O-(trimethylsilyl)-β-D-thiomannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 94 percent / potassium iodide; silver(I) oxide; sym-collidine / CH₂Cl₂ / 17 h / 0 - 20 °C

2.1: sodium cyanoborohydride / tetrahydrofuran / 0.25 h / 0 °C

2.2: 74 percent / hydrochloric acid / tetrahydrofuran; diethyl ether / 12 h / 20 °C

3.1: 95 percent / triethylamine / CH₂Cl₂ / 1 h / -20 °C

With 2,4,6-trimethyl-pyridine; sodium cyanoborohydride; triethylamine; potassium iodide; silver(l) oxide; In tetrahydrofuran; dichloromethane;
DOI:10.1016/j.tetasy.2004.11.032

Reference yield:

: (3aS,4S,5aR,8R,9aR,9bS)-2,2-Dibutyl-8-phenyl-4-phenylsulfanyl-hexahydro-1,3,5,7,9-pentaoxa-2-stanna-cyclopenta[a]naphthalene

: 848397-77-3
S-phenyl 3,6-di-O-benzyl-2-O-(p-toluenesulfonyl)-4-O-(trimethylsilyl)-β-D-thiomannopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: 43 mg / tetrabutylammonium iodide / toluene / 8 h / 100 °C

2.1: 94 percent / potassium iodide; silver(I) oxide; sym-collidine / CH₂Cl₂ / 17 h / 0 - 20 °C

3.1: sodium cyanoborohydride / tetrahydrofuran / 0.25 h / 0 °C

3.2: 74 percent / hydrochloric acid / tetrahydrofuran; diethyl ether / 12 h / 20 °C

4.1: 95 percent / triethylamine / CH₂Cl₂ / 1 h / -20 °C

With 2,4,6-trimethyl-pyridine; tetra-(n-butyl)ammonium iodide; sodium cyanoborohydride; triethylamine; potassium iodide; silver(l) oxide; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1016/j.tetasy.2004.11.032