(3S,6R,7R,12S,10E)-12-(benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-3,7-dimethyloxacyclododec-10-en-2-one

Base Information

• Chemical Name: (3S,6R,7R,12S,10E)-12-(benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-3,7-dimethyloxacyclododec-10-en-2-one
• CAS No.: 1123785-03-4
• Molecular Formula: C₂₇H₄₄O₄Si
• Molecular Weight: 460.729

Synonyms:(3S,6R,7R,12S,10E)-12-(benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-3,7-dimethyloxacyclododec-10-en-2-one

Chemical Property of (3S,6R,7R,12S,10E)-12-(benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-3,7-dimethyloxacyclododec-10-en-2-one

Chemical Property:

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Technology Process of (3S,6R,7R,12S,10E)-12-(benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-3,7-dimethyloxacyclododec-10-en-2-one

There total 37 articles about (3S,6R,7R,12S,10E)-12-(benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-3,7-dimethyloxacyclododec-10-en-2-one 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: 42.0%

(2S,5R,6R,11S,9E)-12-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-11-hydroxy-2,6-dimethyldodec-9-enoic acid (1123785-57-8) → (3S,6R,7R,12S,10E)-12-(benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-3,7-dimethyloxacyclododec-10-en-2-one (1123785-03-4)

Guidance literature:

(2S,5R,6R,11S,9E)-12-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-11-hydroxy-2,6-dimethyldodec-9-enoic acid; With [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; 1-ethoxyacetylene; In toluene; at 0 - 20 ℃; for 0.5h;

With camphor-10-sulfonic acid; In toluene; at 20 - 50 ℃; for 2h; diastereoselective reaction;

DOI:10.1016/j.tetlet.2008.11.088

Reference yield:

(2S,5R,6R,11S,9E)-12-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-11-hydroxy-2,6-dimethyldodec-9-enoic acid (1123785-57-8) → (3S,6R,7R,12S,10E)-12-(benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-3,7-dimethyloxacyclododec-10-en-2-one (1123785-03-4) + (3R,6R,7R,12S,10E)-12-(benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-3,7-dimethyloxacyclododec-10-en-2-one (1123785-59-0)

Guidance literature:

(2S,5R,6R,11S,9E)-12-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-11-hydroxy-2,6-dimethyldodec-9-enoic acid; With 2,4,6-trichlorobenzoyl chloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 20 ℃;

With dmap; In benzene; at 80 ℃;

DOI:10.1016/j.tetlet.2008.11.088

Reference yield:

ethoxyvinyl ester → (3S,6R,7R,12S,10E)-12-(benzyloxymethyl)-6-(tert-butyldimethylsilyloxy)-3,7-dimethyloxacyclododec-10-en-2-one (1123785-03-4)

Guidance literature:

With camphor-10-sulfonic acid; In toluene; at 50 ℃; for 2h;

DOI:10.1016/j.tetasy.2012.07.006

upstream raw materials:

(2S,5R,6R,11S,9E)-12-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-11-hydroxy-2,6-dimethyldodec-9-enoic acid

(S)-4-benzyl-3-((S)-2-methylpent-4-enoyl)oxazolidin-2-one

(4R,5R,8S,)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4,8-dimethylnonan-1-ol

5-((4R,5R,8S,)-9-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-4,8-dimethylnonylsulfonyl)-1-phenyl-1H-tetrazole

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