(1R,3aS,4S,5S,7S,7aS,9R)-9-(tert-Butyl-diphenyl-silanyloxymethyl)-5,7-bis-methoxymethoxy-7a-methyl-octahydro-4,7-ethano-inden-1-ol

Base Information

• Chemical Name: (1R,3aS,4S,5S,7S,7aS,9R)-9-(tert-Butyl-diphenyl-silanyloxymethyl)-5,7-bis-methoxymethoxy-7a-methyl-octahydro-4,7-ethano-inden-1-ol
• CAS No.: 313944-69-3
• Molecular Formula: C₃₃H₄₈O₆Si
• Molecular Weight: 568.826
• Mol file: 313944-69-3.mol

Synonyms:

Chemical Property of (1R,3aS,4S,5S,7S,7aS,9R)-9-(tert-Butyl-diphenyl-silanyloxymethyl)-5,7-bis-methoxymethoxy-7a-methyl-octahydro-4,7-ethano-inden-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,3aS,4S,5S,7S,7aS,9R)-9-(tert-Butyl-diphenyl-silanyloxymethyl)-5,7-bis-methoxymethoxy-7a-methyl-octahydro-4,7-ethano-inden-1-ol

There total 8 articles about (1R,3aS,4S,5S,7S,7aS,9R)-9-(tert-Butyl-diphenyl-silanyloxymethyl)-5,7-bis-methoxymethoxy-7a-methyl-octahydro-4,7-ethano-inden-1-ol 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: 99.0%

C33H46O6Si (313944-61-5) → (1R,3aS,4S,5S,7S,7aS,9R)-9-(tert-Butyl-diphenyl-silanyloxymethyl)-5,7-bis-methoxymethoxy-7a-methyl-octahydro-4,7-ethano-inden-1-ol (313944-69-3)

Guidance literature:

With lithium triethylborohydride;

DOI:10.1016/S0040-4039(00)01413-1

Reference yield:

(1S,2R,3S,4S,5R,8S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1,8-bis-methoxymethoxy-2-methyl-3-(2-oxo-ethyl)-bicyclo[2.2.2]octane-2-carbaldehyde (313944-59-1) → (1R,3aS,4S,5S,7S,7aS,9R)-9-(tert-Butyl-diphenyl-silanyloxymethyl)-5,7-bis-methoxymethoxy-7a-methyl-octahydro-4,7-ethano-inden-1-ol (313944-69-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / SmI₂ / tetrahydrofuran; hexamethylphosphoric acid triamide / 20 °C

2: 91 percent / Ph₃P; DEAD

3: 99 percent / Super-Hydride

With samarium diiodide; lithium triethylborohydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1: Cyclization / 2: Epoxidation / 3: Reduction;

DOI:10.1016/S0040-4039(00)01413-1

Reference yield:

2-[(1S,2S,3S,4S,6R,7S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxymethyl-4,7-bis-methoxymethoxy-3-methyl-bicyclo[2.2.2]oct-2-yl]-ethanol (313944-68-2) → (1R,3aS,4S,5S,7S,7aS,9R)-9-(tert-Butyl-diphenyl-silanyloxymethyl)-5,7-bis-methoxymethoxy-7a-methyl-octahydro-4,7-ethano-inden-1-ol (313944-69-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 62 percent / PCC

2: 74 percent / SmI₂ / tetrahydrofuran; hexamethylphosphoric acid triamide / 20 °C

3: 91 percent / Ph₃P; DEAD

4: 99 percent / Super-Hydride

With samarium diiodide; lithium triethylborohydride; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1: Oxidation / 2: Cyclization / 3: Epoxidation / 4: Reduction;

DOI:10.1016/S0040-4039(00)01413-1

upstream raw materials:

C₃₃H₄₆O₆Si

(1S,2R,3S,4S,5R,8S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1,8-bis-methoxymethoxy-2-methyl-3-(2-oxo-ethyl)-bicyclo[2.2.2]octane-2-carbaldehyde

(1S,2S,3aS,4S,5S,7S,7aS,9R)-9-(tert-Butyl-diphenyl-silanyloxymethyl)-5,7-bis-methoxymethoxy-7a-methyl-octahydro-4,7-ethano-indene-1,2-diol

2-[(1S,2S,3S,4S,6R,7S)-6-(tert-Butyl-diphenyl-silanyloxymethyl)-3-hydroxymethyl-4,7-bis-methoxymethoxy-3-methyl-bicyclo[2.2.2]oct-2-yl]-ethanol

Downstream raw materials:

(1R,3aS,4S,7S,7aS,9R)-1-Benzyloxy-9-(tert-butyl-diphenyl-silanyloxymethyl)-7-hydroxy-7a-methyl-octahydro-4,7-ethano-inden-5-one

(3R,3aS,4S,6S,7S,7aS,8R)-3-Benzyloxy-8-(tert-butyl-diphenyl-silanyloxymethyl)-3a-methyl-octahydro-4,7-ethano-indene-4,6-diol

((3R,3aS,4S,6S,7S,7aS,8R)-3-Benzyloxy-4,6-bis-methoxymethoxy-3a-methyl-octahydro-4,7-ethano-inden-8-ylmethoxy)-tert-butyl-diphenyl-silane