(1S,4S)-1-(tert-butyldiphenylsilyloxy)-4-iodomethylcyclohex-2-ene

Base Information

• Chemical Name: (1S,4S)-1-(tert-butyldiphenylsilyloxy)-4-iodomethylcyclohex-2-ene
• CAS No.: 153832-97-4
• Molecular Formula: C₂₃H₂₉IOSi
• Molecular Weight: 476.473
• Mol file: 153832-97-4.mol

Synonyms:(1S,4S)-1-(tert-butyldiphenylsilyloxy)-4-iodomethylcyclohex-2-ene

Chemical Property of (1S,4S)-1-(tert-butyldiphenylsilyloxy)-4-iodomethylcyclohex-2-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,4S)-1-(tert-butyldiphenylsilyloxy)-4-iodomethylcyclohex-2-ene

There total 1 articles about (1S,4S)-1-(tert-butyldiphenylsilyloxy)-4-iodomethylcyclohex-2-ene 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: 74.0%

(1S,4S)-1-(tert-butyldiphenylsilyloxy)-4-<(methanesulphonyloxy)methyl>cyclohex-2-ene → (1S,4S)-1-(tert-butyldiphenylsilyloxy)-4-iodomethylcyclohex-2-ene (153832-97-4)

Guidance literature:

In acetone; for 21h; Heating;

DOI:10.1016/0040-4020(95)98714-S

Reference yield: 68.0%

(2R)-2,5-dihydro-2-isopropyl-3,6-dimethoxypyrazine (109838-85-9) + (1S,4S)-1-(tert-butyldiphenylsilyloxy)-4-iodomethylcyclohex-2-ene (153832-97-4) → (2R,5R)-2-<<(1'S,4'S)-1'-(tert-butyldiphenylsilyloyx)cyclohex-2'-en-4'-yl>methyl>-2,5-dihydro-5-isopropyl-3,6-dimethoxypyrazine

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 - -21 ℃; for 24h;

DOI:10.1016/0040-4020(95)98714-S

Reference yield:

(1S,4S)-1-(tert-butyldiphenylsilyloxy)-4-iodomethylcyclohex-2-ene (153832-97-4) → N-acetyl-β-<(1S,4S)-1-hydroxycyclohex-2-en-4-yl>-(S)-alanine methyl ester (153833-01-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) n-BuLi, 2.) CuCN

2: 0.25 M HCl / acetonitrile / 2 h / Ambient temperature

3: pyridine / 3 h / Ambient temperature

4: 88 percent / NH₄F / methanol / 18 h / 50 °C

With pyridine; hydrogenchloride; ammonium fluoride; n-butyllithium; In methanol; acetonitrile;

DOI:10.1039/c39930001332

Downstream raw materials:

anticapsin

N-acetyl-β-<(1S,4S)-1-hydroxycyclohex-2-en-4-yl>-(S)-alanine methyl ester

β-<(1S,4S)-1-(tert-btuyldiphenylsilyloxy)cyclohex2-en-4-yl>-(S)-alanine methyl ester

N-acetyl-β-<(1S,4S)-1-(tert-butyldiphenylsilyloxy)cyclohex-2-en-4-yl>-(S)-alanine methyl ester