(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

Base Information

• Chemical Name: (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
• CAS No.: 313944-59-1
• Molecular Formula: C₃₃H₄₆O₇Si
• Molecular Weight: 582.81
• Mol file: 313944-59-1.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 5 articles about (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 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: 62.0%

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) → (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)

Guidance literature:

With pyridinium chlorochromate;

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

Reference yield:

(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) → (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)

Guidance literature:

Multi-step reaction with 4 steps

1: 100 percent / iPr₂NEt

2: 96 percent / LiAlH₄

3: 96 percent / PPTS / methanol

4: 62 percent / PCC

With lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; N-ethyl-N,N-diisopropylamine; pyridinium chlorochromate; In methanol; 1: Etherification / 2: Reduction / 3: Substitution / 4: Oxidation;

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

Reference yield:

(1S,2R,3S,4S,5R,8S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(tert-butyl-diphenyl-silanyloxymethyl)-1,8-bis-methoxymethoxy-2-methyl-bicyclo[2.2.2]octane-2-carboxylic acid methyl ester (313944-66-0) → (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)

Guidance literature:

Multi-step reaction with 3 steps

1: 96 percent / LiAlH₄

2: 96 percent / PPTS / methanol

3: 62 percent / PCC

With lithium aluminium tetrahydride; pyridinium p-toluenesulfonate; pyridinium chlorochromate; In methanol; 1: Reduction / 2: Substitution / 3: Oxidation;

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

upstream raw materials:

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

(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

(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,2S,3S,4S,5R,8S)-3-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(tert-butyl-diphenyl-silanyloxymethyl)-1,8-bis-methoxymethoxy-2-methyl-bicyclo[2.2.2]oct-2-yl]-methanol

Downstream raw materials:

((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

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

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

C₃₃H₄₆O₆Si