1-adamantyl 4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-β-L-rhamnopyranoside

Base Information

Chemical Name:1-adamantyl 4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-β-L-rhamnopyranoside
CAS No.:503065-99-4
Molecular Formula:C₃₇H₃₉F₃O₈S
Molecular Weight:700.773
Hs Code.:

Synonyms:1-adamantyl 4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-β-L-rhamnopyranoside

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Chemical Property of 1-adamantyl 4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-β-L-rhamnopyranoside

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Technology Process of 1-adamantyl 4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-β-L-rhamnopyranoside

There total 8 articles about 1-adamantyl 4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-β-L-rhamnopyranoside 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%

: 358-23-6
trifluoromethylsulfonic anhydride

: 768-95-6
1-adamanthanol

: 503065-97-2
phenyl 4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-1-thio-β-L-rhamnopyranoside

: 503065-99-4
1-adamantyl 4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-β-L-rhamnopyranoside

Guidance literature:: trifluoromethylsulfonic anhydride; phenyl 4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-1-thio-β-L-rhamnopyranoside; With 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; at -60 ℃; for 1h;

1-adamanthanol; In dichloromethane; at -60 - 20 ℃; for 3.5h; Further stages.;
DOI:10.1021/ol0340890

Reference yield:

: 776-04-5
2-trifluoromethylbenzenesulfonyl chloride

: 503065-99-4
1-adamantyl 4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-β-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1.1: 52 percent / Ag₂O; KI; collidine / CH₂Cl₂ / 37 h / 0 - 20 °C

2.1: 88 percent / DMAP / CH₂Cl₂ / 3 h / 20 °C

3.1: 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine / CH₂Cl₂ / 1 h / -60 °C

3.2: 81 percent / CH₂Cl₂ / 3.5 h / -60 - 20 °C

With 2,3,5-trimethyl-pyridine; dmap; 1-benzenesulfinyl piperidine; potassium iodide; silver(l) oxide; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane;
DOI:10.1021/ol0340890

Reference yield:

: 100-39-0
benzyl bromide

: 503065-99-4
1-adamantyl 4-O-benzoyl-3-O-benzyl-2-O-(2-trifluoromethylbenzenesulfonyl)-β-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1.1: Bu₂SnO / benzene / 4 h / Heating

1.2: 71 percent / CsF / dimethylformamide / 18 h / 20 °C

2.1: 52 percent / Ag₂O; KI; collidine / CH₂Cl₂ / 37 h / 0 - 20 °C

3.1: 88 percent / DMAP / CH₂Cl₂ / 3 h / 20 °C

4.1: 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyrimidine / CH₂Cl₂ / 1 h / -60 °C

4.2: 81 percent / CH₂Cl₂ / 3.5 h / -60 - 20 °C

With 2,3,5-trimethyl-pyridine; dmap; 1-benzenesulfinyl piperidine; di(n-butyl)tin oxide; potassium iodide; silver(l) oxide; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; benzene;
DOI:10.1021/ol0340890