[(1S,2S,3S,6S)-6-tert-Butoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-1-methyl-cyclohexyl]-acetaldehyde

Base Information

• Chemical Name: [(1S,2S,3S,6S)-6-tert-Butoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-1-methyl-cyclohexyl]-acetaldehyde
• CAS No.: 214549-25-4
• Molecular Formula: C₂₂H₄₄O₅Si
• Molecular Weight: 416.674
• Mol file: 214549-25-4.mol

Synonyms:[(1S,2S,3S,6S)-6-tert-Butoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-1-methyl-cyclohexyl]-acetaldehyde

Chemical Property of [(1S,2S,3S,6S)-6-tert-Butoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-1-methyl-cyclohexyl]-acetaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1S,2S,3S,6S)-6-tert-Butoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-1-methyl-cyclohexyl]-acetaldehyde

There total 6 articles about [(1S,2S,3S,6S)-6-tert-Butoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-1-methyl-cyclohexyl]-acetaldehyde 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: 93.5%

2-[(1S,2S,3S,6S)-6-tert-Butoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-1-methyl-cyclohexyl]-ethanol (214549-22-1) → [(1S,2S,3S,6S)-6-tert-Butoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-1-methyl-cyclohexyl]-acetaldehyde (214549-25-4)

Guidance literature:

With tetrapropylammonium perruthennate; 4 A molecular sieve; 4-methylmorpholine N-oxide; In acetonitrile; for 0.5h; Ambient temperature;

DOI:10.1055/s-1998-1833

Reference yield:

2-((4aS,5S,6S,8aS)-6-tert-Butoxy-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxin-5-yl)-ethanol (155095-85-5) → [(1S,2S,3S,6S)-6-tert-Butoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-1-methyl-cyclohexyl]-acetaldehyde (214549-25-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / Et₃N / CH₂Cl₂ / 1 h / Ambient temperature

2: 98 percent / aq. TsOH / ethanol / 0.5 h / Ambient temperature

3: 98 percent / DMAP / CH₂Cl₂ / 1.5 h / 0 - 20 °C

4: 98 percent / iPr₂NEt / CH₂Cl₂ / 12 h / Ambient temperature

5: 100 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / -70 - 0 °C

6: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 30 min, 2.) CH₂Cl₂, 0 deg C

With dmap; lithium aluminium tetrahydride; oxalyl dichloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; ethanol; dichloromethane;

DOI:10.1016/S0957-4166(99)00062-2

Reference yield:

Benzoic acid 2-((1S,2S,3S,6S)-6-tert-butoxy-3-hydroxy-2-hydroxymethyl-1-methyl-cyclohexyl)-ethyl ester (214549-16-3) → [(1S,2S,3S,6S)-6-tert-Butoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-1-methyl-cyclohexyl]-acetaldehyde (214549-25-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 98 percent / DMAP / CH₂Cl₂ / 1.5 h / 0 - 20 °C

2: 98 percent / iPr₂NEt / CH₂Cl₂ / 12 h / Ambient temperature

3: 100 percent / LiAlH₄ / tetrahydrofuran / 0.5 h / -70 - 0 °C

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -60 deg C, 30 min, 2.) CH₂Cl₂, 0 deg C

With dmap; lithium aluminium tetrahydride; oxalyl dichloride; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0957-4166(99)00062-2

upstream raw materials:

2-[(1S,2S,3S,6S)-6-tert-Butoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-1-methyl-cyclohexyl]-ethanol

2-((4aS,5S,6S,8aS)-6-tert-Butoxy-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxin-5-yl)-ethanol

Benzoic acid 2-((1S,2S,3S,6S)-6-tert-butoxy-3-hydroxy-2-hydroxymethyl-1-methyl-cyclohexyl)-ethyl ester

Benzoic acid 2-((4aS,5S,6S,8aS)-6-tert-butoxy-2,2,5-trimethyl-hexahydro-benzo[1,3]dioxin-5-yl)-ethyl ester

Downstream raw materials:

1-[2-((1S,2S,3S,6S)-6-tert-Butoxy-2-hydroxymethyl-3-methoxymethoxy-1-methyl-cyclohexyl)-1-methoxymethoxy-ethyl]-2,6,6-trimethyl-cyclohex-2-ene-1,4-diol

1-{2-[(1S,2S,3S,6S)-6-tert-Butoxy-2-(tert-butyl-dimethyl-silanyloxymethyl)-3-methoxymethoxy-1-methyl-cyclohexyl]-1-methoxymethoxy-ethyl}-4-(tert-butyl-dimethyl-silanyloxy)-2,6,6-trimethyl-cyclohex-2-enol