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

Base Information

• Chemical Name: (1R,3S,4R,5S)-[4-benzyloxy-1,6-dimethyl-2-iodomethyl]cyclohexyliodomethane
• CAS No.: 151433-58-8
• Molecular Formula: C₁₇H₂₄I₂O
• Molecular Weight: 498.186
• Mol file: 151433-58-8.mol

Synonyms:(1R,3S,4R,5S)-[4-benzyloxy-1,6-dimethyl-2-iodomethyl]cyclohexyliodomethane

Chemical Property of (1R,3S,4R,5S)-[4-benzyloxy-1,6-dimethyl-2-iodomethyl]cyclohexyliodomethane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3S,4R,5S)-[4-benzyloxy-1,6-dimethyl-2-iodomethyl]cyclohexyliodomethane

There total 21 articles about (1R,3S,4R,5S)-[4-benzyloxy-1,6-dimethyl-2-iodomethyl]cyclohexyliodomethane 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:

Trifluoro-methanesulfonic acid (1R,2S,4R,6S)-4-benzyloxy-1,2-dimethyl-6-trifluoromethanesulfonyloxymethyl-cyclohexylmethyl ester (133661-23-1) → (1RS,3SR,4RS,5SR)-[4-benzyloxy-1,6-dimethyl-2-iodomethyl]cyclohexyliodomethane (133661-22-0,151433-58-8)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; In toluene; at 20 ℃; Yield given;

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

Reference yield:

Trifluoro-methanesulfonic acid (1R,2S,4R,6S)-4-benzyloxy-1,2-dimethyl-6-trifluoromethanesulfonyloxymethyl-cyclohexylmethyl ester → (1R,3S,4R,5S)-[4-benzyloxy-1,6-dimethyl-2-iodomethyl]cyclohexyliodomethane (151433-58-8)

Guidance literature:

Yield given;

DOI:10.1016/S0040-4039(00)79251-3

Reference yield:

4,5-dimethyl-3-cyclohexen-1-one (133661-15-1) → (1RS,3SR,4RS,5SR)-[4-benzyloxy-1,6-dimethyl-2-iodomethyl]cyclohexyliodomethane (133661-22-0,151433-58-8)

Guidance literature:

Multi-step reaction with 7 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

6: 0.875 g / (n-Bu)4NI / toluene / 20 h / 20 °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; toluene;

DOI:10.1021/ja0208456

upstream raw materials:

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

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

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

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

Downstream raw materials:

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

(1R,3S,4R,5S)-3,4-diiodomethyl-4,5-dimethylcyclohexan-1-one

(1R,3S,4R,5S)-3,4-diiodomethyl-4,5-dimethylcyclohexan-1-ol

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