(2R,3R,5R,6S,7S,8R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsilyloxy)-7-hydroxy-8-hydroxymethyl-5-(4-methoxybenzyloxy)-4,4-dimethylcyclooctanone

Base Information

• Chemical Name: (2R,3R,5R,6S,7S,8R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsilyloxy)-7-hydroxy-8-hydroxymethyl-5-(4-methoxybenzyloxy)-4,4-dimethylcyclooctanone
• CAS No.: 409319-61-5
• Molecular Formula: C₃₉H₅₄O₈Si
• Molecular Weight: 678.938

Synonyms:(2R,3R,5R,6S,7S,8R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsilyloxy)-7-hydroxy-8-hydroxymethyl-5-(4-methoxybenzyloxy)-4,4-dimethylcyclooctanone

Chemical Property of (2R,3R,5R,6S,7S,8R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsilyloxy)-7-hydroxy-8-hydroxymethyl-5-(4-methoxybenzyloxy)-4,4-dimethylcyclooctanone

Chemical Property:

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Technology Process of (2R,3R,5R,6S,7S,8R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsilyloxy)-7-hydroxy-8-hydroxymethyl-5-(4-methoxybenzyloxy)-4,4-dimethylcyclooctanone

There total 7 articles about (2R,3R,5R,6S,7S,8R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsilyloxy)-7-hydroxy-8-hydroxymethyl-5-(4-methoxybenzyloxy)-4,4-dimethylcyclooctanone 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: 45.0%

(2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(t-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxiranyl-7-oxapentanal (409319-63-7) → (2R,3R,5R,6S,7R,8S)-2,6-bis(benzyloxy)-3-(t-butyldimethylsilyloxy)-7-hydroxy-8-hydroxymethyl-5-(4-methoxybenzyloxy)-4,4-dimethylcyclooctanone (409319-74-0) + (2R,3R,5R,6S,7S,8R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsilyloxy)-7-hydroxy-8-hydroxymethyl-5-(4-methoxybenzyloxy)-4,4-dimethylcyclooctanone (409319-61-5)

Guidance literature:

With samarium diiodide; isopropyl alcohol; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1246/cl.2002.82

Reference yield: 12.0%

(2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(t-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxiranyl-7-oxapentanal (409319-63-7) → (2R,3R,5R,6R)-2,6-Bis-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-9-hydroxy-3-(4-methoxy-benzyloxy)-4,4-dimethyl-7-oxo-nonanal + (2R,3R,5R,6S,7R,8S)-2,6-bis(benzyloxy)-3-(t-butyldimethylsilyloxy)-7-hydroxy-8-hydroxymethyl-5-(4-methoxybenzyloxy)-4,4-dimethylcyclooctanone (409319-74-0) + (2R,3R,5R,6S,7S,8R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsilyloxy)-7-hydroxy-8-hydroxymethyl-5-(4-methoxybenzyloxy)-4,4-dimethylcyclooctanone (409319-61-5)

Guidance literature:

With samarium diiodide; water; In tetrahydrofuran; at -78 ℃;

DOI:10.1246/bcsj.78.677

Reference yield: 10.0%

(2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(t-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxiranyl-7-oxapentanal (409319-63-7) → (4S,5R,7S)-4-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-2-hydroxymethyl-5-(4-methoxy-benzyloxy)-6,6-dimethyl-cyclooctanone + (2R,3R,5R,6S,7R,8S)-2,6-bis(benzyloxy)-3-(t-butyldimethylsilyloxy)-7-hydroxy-8-hydroxymethyl-5-(4-methoxybenzyloxy)-4,4-dimethylcyclooctanone (409319-74-0) + (2R,3R,5R,6S,7S,8R)-2,6-bis(benzyloxy)-3-(t-butyldimethylsilyloxy)-7-hydroxy-8-hydroxymethyl-5-(4-methoxybenzyloxy)-4,4-dimethylcyclooctanone (409319-61-5)

Guidance literature:

With samarium diiodide; In tetrahydrofuran; at -78 ℃;

DOI:10.1246/cl.2002.82

upstream raw materials:

(2R,3R,5R,6R)-2,6-bis(benzyloxy)-5-(t-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)-4,4-dimethyl-7-oxiranyl-7-oxapentanal

(2R,3R,5R,6S)-2,6-Dibenzyloxy-3,7-bis(tert-butyldimethylsiloxy)-5-(p-methoxybenzyloxy)-4,4-dimethylheptanal

(2S,3R,5R,6S)-2,6-bis(benzyloxy)-3-(t-butyldimethylsilyloxy)-5-(4-methoxybenzyloxy)-4,4-dimethyl-1-oxiranylheptane-1,7-diol

(2S,3R,5R,6S)-2,6-bis(benzyloxy)-5-(t-butyldimethylsilyloxy)-3-(4-methoxybenzyloxy)-4,4-dimethylnon-8-ene-1,7-diol

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