(3S,4R,5S,6R)-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)-1,2-epoxyheptane

Base Information

• Chemical Name: (3S,4R,5S,6R)-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)-1,2-epoxyheptane
• CAS No.: 898801-53-1
• Molecular Formula: C₄₂H₅₀O₆Si
• Molecular Weight: 678.941
• Mol file: 898801-53-1.mol

Synonyms:(3S,4R,5S,6R)-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)-1,2-epoxyheptane

Chemical Property of (3S,4R,5S,6R)-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)-1,2-epoxyheptane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,5S,6R)-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)-1,2-epoxyheptane

There total 9 articles about (3S,4R,5S,6R)-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)-1,2-epoxyheptane 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: 87.0%

(3S,4R,5S,6R)-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)heptene (898801-59-7) → (3S,4R,5S,6R)-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)-1,2-epoxyheptane (898801-53-1)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 20 ℃; for 60h;

DOI:10.1055/s-2006-939693

Reference yield:

(2R,3S,4S,5S)-4,5-dibenzyloxyhept-6-en-1,2,3-triol (898801-57-5) → (3S,4R,5S,6R)-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)-1,2-epoxyheptane (898801-53-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 83 percent / TEA; DMAP / CH₂Cl₂ / 72 h / 0 - 20 °C

2: 93 percent / CSA / methanol / 0.42 h / 20 °C

3: 87 percent / MCPBA / CH₂Cl₂ / 60 h / 0 - 20 °C

With dmap; TEA; camphor-10-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;

DOI:10.1055/s-2006-939693

Reference yield:

(2R,3S,4R,5S)-4,5-di-O-benzyl-1,3-O-benzylidenehept-6-ene-1,2,3,4,5-pentaol (958265-80-0) → (3S,4R,5S,6R)-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)-1,2-epoxyheptane (898801-53-1)

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / CSA; 1,3-propanedithiol / methanol / 15 h / 20 °C

2: 83 percent / TEA; DMAP / CH₂Cl₂ / 72 h / 0 - 20 °C

3: 93 percent / CSA / methanol / 0.42 h / 20 °C

4: 87 percent / MCPBA / CH₂Cl₂ / 60 h / 0 - 20 °C

With 1.3-propanedithiol; dmap; TEA; camphor-10-sulfonic acid; 3-chloro-benzenecarboperoxoic acid; In methanol; dichloromethane;

DOI:10.1055/s-2006-939693

upstream raw materials:

(3S,4R,5S,6R)-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)heptene

(2R,3S,4S,5S)-4,5-dibenzyloxyhept-6-en-1,2,3-triol

(2R,3S,4R,5S)-4,5-di-O-benzyl-1,3-O-benzylidenehept-6-ene-1,2,3,4,5-pentaol

(2R,3S,4S,5S)-4,5-dibenzyloxy-1-(tert-butyldiphenylsilyloxy)hept-6-en-2,3-diol

Downstream raw materials:

(3R,4S,5S,6R)-1-azido-3,4-dibenzyloxy-7-(tert-butyldiphenylsilyloxy)-5,6-(cyclopentylidenedioxy)heptan-2-one

(1S,3R,4S,5S,6R)-1-azidomethyl-3-(tert-butyldiphenylsilyloxymethyl)-5,6-dibenzyloxy-2,7-dioxabicyclo[2.2.1]heptane

(1R,3S,4R,5S,6R)-1-azidomethyl-5,6-dibenzyloxy-2,7-dioxabicyclo[2.2.1]heptane-3-carboxylic acid

(1S,3R,4S,5S,6R)-1-azidomethyl-5,6-dibenzyloxy-3-hydroxymethyl-2,7-dioxabicyclo[2.2.1]heptane