(1S,2R,5S,6R,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octane-6-carbaldehyde

Base Information

• Chemical Name: (1S,2R,5S,6R,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octane-6-carbaldehyde
• CAS No.: 1352577-34-4
• Molecular Formula: C₃₃H₅₀O₄Si₂
• Molecular Weight: 566.929
• Mol file: 1352577-34-4.mol

Synonyms:(1S,2R,5S,6R,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octane-6-carbaldehyde

Chemical Property of (1S,2R,5S,6R,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octane-6-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,5S,6R,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octane-6-carbaldehyde

There total 10 articles about (1S,2R,5S,6R,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octane-6-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: 97.0%

((1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octan-6-yl)methanol (1352577-38-8) → (1S,2R,5S,6R,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octane-6-carbaldehyde (1352577-34-4)

Guidance literature:

With tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane; at 0 - 23 ℃; for 1.11667h; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.tet.2011.09.079

Reference yield:

(1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-hydroxyethyl)-5-methyl-8-oxabicyclo[3.2.1]octane-6-carboxylic acid (1352577-48-0) → (1S,2R,5S,6R,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octane-6-carbaldehyde (1352577-34-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 16.25 h / 23 - 35 °C / Inert atmosphere

2.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / benzene / 20 h / 75 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / diethyl ether / 42 h / -40 °C / Inert atmosphere

3.2: 1.5 h / -40 - 23 °C / Inert atmosphere

4.1: pyridine; dmap / 21 h / 23 °C / Inert atmosphere

5.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1.12 h / 0 - 23 °C / Inert atmosphere; Molecular sieve

With pyridine; dmap; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; benzotriazol-1-ol; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In diethyl ether; dichloromethane; benzene;

DOI:10.1016/j.tet.2011.09.079

Reference yield:

2-((1S,4R,5S,6S,7S)-4-(tert-butyldimethylsilyloxy)-7-(hydroxymethyl)-1-methyl-8-oxabicyclo[3.2.1]octan-6-yl)ethanol (1352577-49-1) → (1S,2R,5S,6R,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-(tert-butyldiphenylsilyloxy)ethyl)-5-methyl-8-oxabicyclo[3.2.1]octane-6-carbaldehyde (1352577-34-4)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine; dmap / 21 h / 23 °C / Inert atmosphere

2: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 1.12 h / 0 - 23 °C / Inert atmosphere; Molecular sieve

With pyridine; dmap; tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In dichloromethane;

DOI:10.1016/j.tet.2011.09.079

upstream raw materials:

(1S,2R,5S,6S,7S)-2-(tert-butyldimethylsilyloxy)-7-(2-hydroxyethyl)-5-methyl-8-oxabicyclo[3.2.1]octane-6-carboxylic acid

(1S,2S,7S,8S,9R)-9-(tert-butyldimethylsilyloxy)-1-methyl-4,12-dioxa-tricyclo[6.3.1.0(2,7)]dodecan-3-one

(1S,2R,7S,8S,9R)-9-(tert-butyldimethylsilyloxy)-1-methyl-4,12-dioxa-tricyclo[6.3.1.0(2,7)]dodecan-3-one

2-((1S,4R,5S,6S,7S)-4-(tert-butyldimethylsilyloxy)-7-(hydroxymethyl)-1-methyl-8-oxabicyclo[3.2.1]octan-6-yl)ethanol

Downstream raw materials:

tert-butyl((2-(1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)ethoxy)diphenylsilane

(5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)-1-hydroxyethyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one

(5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)ethanoyl)-5-isobutyl-1-(phenylcarbonyl)pyrrolidin-2-one

(5S)-3-(2-((1S,4R,5S,6S,7R)-4-(tert-butyldimethylsilyloxy)-1-methyl-7-((1E,3E)-3-methylpenta-1,3-dienyl)-8-oxabicyclo[3.2.1]octan-6-yl)ethanoyl)-5-isobutyl-1-(phenylcarbonyl)-3-(phenylselanyl)pyrrolidin-2-one