(1S,2R,3S,4S,5R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-methoxymethoxy-2-methyl-8-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (1S,2R,3S,4S,5R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-methoxymethoxy-2-methyl-8-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester
• CAS No.: 313944-58-0
• Molecular Formula: C₃₈H₅₈O₇Si₂
• Molecular Weight: 683.045
• Mol file: 313944-58-0.mol

Synonyms:(1S,2R,3S,4S,5R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-methoxymethoxy-2-methyl-8-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

Chemical Property of (1S,2R,3S,4S,5R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-methoxymethoxy-2-methyl-8-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3S,4S,5R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-methoxymethoxy-2-methyl-8-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

There total 1 articles about (1S,2R,3S,4S,5R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-methoxymethoxy-2-methyl-8-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl 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: 65.0%

5-(tert-butyl-dimethyl-silanyloxy)-2-methyl-pent-2-enoic acid methyl ester + 5-(tert-butyl-diphenyl-silanyloxymethyl)-3-methoxymethoxy-cyclohex-2-enone → (1S,2R,3S,4S,5R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-methoxymethoxy-2-methyl-8-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester (313944-58-0)

Guidance literature:

With lithium diisopropyl amide; In tetrahydrofuran; at 20 ℃;

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

Reference yield: 73.0%

(1S,2R,3S,4S,5R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-methoxymethoxy-2-methyl-8-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester (313944-58-0) → (1S,2R,3S,4S,5R,8S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(tert-butyl-diphenyl-silanyloxymethyl)-8-hydroxy-1-methoxymethoxy-2-methyl-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester (313944-65-9)

Guidance literature:

With sodium tetrahydroborate;

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

Reference yield:

(1S,2R,3S,4S,5R)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(tert-butyl-diphenyl-silanyloxymethyl)-1-methoxymethoxy-2-methyl-8-oxo-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester (313944-58-0) → (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 8 steps

1: 73 percent / NaBH₄

2: 100 percent / iPr₂NEt

3: 96 percent / LiAlH₄

4: 96 percent / PPTS / methanol

5: 62 percent / PCC

6: 74 percent / SmI₂ / tetrahydrofuran; hexamethylphosphoric acid triamide / 20 °C

7: 91 percent / Ph₃P; DEAD

8: 99 percent / Super-Hydride

With sodium tetrahydroborate; lithium aluminium tetrahydride; samarium diiodide; pyridinium p-toluenesulfonate; lithium triethylborohydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; pyridinium chlorochromate; diethylazodicarboxylate; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; 1: Reduction / 2: Etherification / 3: Reduction / 4: Substitution / 5: Oxidation / 6: Cyclization / 7: Epoxidation / 8: Reduction;

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

Downstream raw materials:

(1S,2R,3S,4S,5R,8S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(tert-butyl-diphenyl-silanyloxymethyl)-8-hydroxy-1-methoxymethoxy-2-methyl-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester

(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

(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

C₃₃H₄₆O₆Si