Trifluoro-methanesulfonic acid (1R,2S,4R,6S)-4-benzyloxy-1,2-dimethyl-6-trifluoromethanesulfonyloxymethyl-cyclohexylmethyl ester

Base Information

• Chemical Name: Trifluoro-methanesulfonic acid (1R,2S,4R,6S)-4-benzyloxy-1,2-dimethyl-6-trifluoromethanesulfonyloxymethyl-cyclohexylmethyl ester
• CAS No.: 133661-23-1
• Molecular Formula: C₁₉H₂₄F₆O₇S₂
• Molecular Weight: 542.518
• Mol file: 133661-23-1.mol

Synonyms:Trifluoro-methanesulfonic acid (1R,2S,4R,6S)-4-benzyloxy-1,2-dimethyl-6-trifluoromethanesulfonyloxymethyl-cyclohexylmethyl ester

Chemical Property of Trifluoro-methanesulfonic acid (1R,2S,4R,6S)-4-benzyloxy-1,2-dimethyl-6-trifluoromethanesulfonyloxymethyl-cyclohexylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Trifluoro-methanesulfonic acid (1R,2S,4R,6S)-4-benzyloxy-1,2-dimethyl-6-trifluoromethanesulfonyloxymethyl-cyclohexylmethyl ester

There total 8 articles about Trifluoro-methanesulfonic acid (1R,2S,4R,6S)-4-benzyloxy-1,2-dimethyl-6-trifluoromethanesulfonyloxymethyl-cyclohexylmethyl ester 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:

trifluoromethylsulfonic anhydride (358-23-6) + ((1R,2S,4R,6S)-4-Benzyloxy-2-hydroxymethyl-1,6-dimethyl-cyclohexyl)-methanol (133661-21-9) → Trifluoro-methanesulfonic acid (1R,2S,4R,6S)-4-benzyloxy-1,2-dimethyl-6-trifluoromethanesulfonyloxymethyl-cyclohexylmethyl ester (133661-23-1)

Guidance literature:

With 2,6-di-tert-butyl-pyridine; In dichloromethane; at -30 ℃;

DOI:10.1016/S0040-4039(00)74881-7

Reference yield:

4,5-dimethyl-3-cyclohexen-1-one (133661-15-1) → Trifluoro-methanesulfonic acid (1R,2S,4R,6S)-4-benzyloxy-1,2-dimethyl-6-trifluoromethanesulfonyloxymethyl-cyclohexylmethyl ester (133661-23-1)

Guidance literature:

Multi-step reaction with 6 steps

1: LS-Selectride / tetrahydrofuran / -100 °C

2: 98 percent / NaH; N-Bu₄NI / tetrahydrofuran / 2 h / Heating

3: POCl₃; Zn-Cu / diethyl ether / 16 h / 20 °C

4: LiAlH₄ / tetrahydrofuran / 12 h / 20 °C

5: 2,6-di-tert-butylpyridine / CH₂Cl₂ / 0.33 h / -30 °C

With lithium aluminium tetrahydride; 2,6-di-tert-butyl-pyridine; tetra-(n-butyl)ammonium iodide; copper; sodium hydride; lithium tri-sec-butyl(hydrido)borate; zinc; trichlorophosphate; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/ja0208456

Reference yield:

(1R,2S,4R,6S)-4-Benzyloxy-8,8-dichloro-1,2-dimethyl-bicyclo[4.2.0]octan-7-one (133661-18-4) → Trifluoro-methanesulfonic acid (1R,2S,4R,6S)-4-benzyloxy-1,2-dimethyl-6-trifluoromethanesulfonyloxymethyl-cyclohexylmethyl ester (133661-23-1)

Guidance literature:

Multi-step reaction with 3 steps

1: LiAlH₄ / tetrahydrofuran / 12 h / 20 °C

2: 2,6-di-tert-butylpyridine / CH₂Cl₂ / 0.33 h / -30 °C

With lithium aluminium tetrahydride; 2,6-di-tert-butyl-pyridine; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja0208456

upstream raw materials:

trifluoromethylsulfonic anhydride

((1R,2S,4R,6S)-4-Benzyloxy-2-hydroxymethyl-1,6-dimethyl-cyclohexyl)-methanol

4,5-dimethyl-3-cyclohexen-1-one

(1SR,5SR)-1-benzyloxy-4,5-dimethylcyclohex-3-ene

Downstream raw materials:

(1RS,3SR,4RS,5SR)-3,4-diiodomethyl-4,5-dimethylcyclohexan-1-ol

(1RS,3SR,4RS,5SR)-3,4-diiodomethyl-4,5-dimethylcyclohexan-1-one

(1RS,3SR,4RS,5SR)-[4-benzyloxy-1,6-dimethyl-2-iodomethyl]cyclohexyliodomethane