(1'R,3S,5S)-2-allyl-6-(tert-butyldiphenylsilanyloxy)benzoic acid 2-hydroxy-5-(1'-methylbut-3'-enyl)tetrahydrofuran-3-yl ester

Base Information

Chemical Name:(1'R,3S,5S)-2-allyl-6-(tert-butyldiphenylsilanyloxy)benzoic acid 2-hydroxy-5-(1'-methylbut-3'-enyl)tetrahydrofuran-3-yl ester
CAS No.:335163-21-8
Molecular Formula:C₃₅H₄₂O₅Si
Molecular Weight:570.801
Hs Code.:

Synonyms:(1'R,3S,5S)-2-allyl-6-(tert-butyldiphenylsilanyloxy)benzoic acid 2-hydroxy-5-(1'-methylbut-3'-enyl)tetrahydrofuran-3-yl ester

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1'R,3S,5S)-2-allyl-6-(tert-butyldiphenylsilanyloxy)benzoic acid 2-hydroxy-5-(1'-methylbut-3'-enyl)tetrahydrofuran-3-yl ester

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Technology Process of (1'R,3S,5S)-2-allyl-6-(tert-butyldiphenylsilanyloxy)benzoic acid 2-hydroxy-5-(1'-methylbut-3'-enyl)tetrahydrofuran-3-yl ester

There total 11 articles about (1'R,3S,5S)-2-allyl-6-(tert-butyldiphenylsilanyloxy)benzoic acid 2-hydroxy-5-(1'-methylbut-3'-enyl)tetrahydrofuran-3-yl ester 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: 90.0%

: 335163-28-5
(1'R,3S,5S)-2-allyl-6-(tert-butyldiphenylsilanyloxy)benzoic acid 5-(1'-methylbut-3'-enyl)-2-oxo-tetrahydrofuran-3-yl ester

: 335163-21-8
(1'R,3S,5S)-2-allyl-6-(tert-butyldiphenylsilanyloxy)benzoic acid 2-hydroxy-5-(1'-methylbut-3'-enyl)tetrahydrofuran-3-yl ester

Guidance literature:: With diisobutylaluminium hydride; In diethyl ether; toluene; at -78 ℃; for 0.5h;
DOI:10.1021/jo0301550

Reference yield:

: 335163-26-3
(1'R,3R,5S)-5-(1'-methylbut-3'-enyl)tetrahydrofuran-2,3-diol

: 335163-21-8
(1'R,3S,5S)-2-allyl-6-(tert-butyldiphenylsilanyloxy)benzoic acid 2-hydroxy-5-(1'-methylbut-3'-enyl)tetrahydrofuran-3-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 95 percent / Ag₂CO₃*celite / benzene / 1 h / Heating

2: 90 percent / diethyl azodicarboxylate; Ph₃P / tetrahydrofuran / -78 - 20 °C

3: 98 percent / imidazole; DMAP / dimethylformamide / 5 h / 20 °C

4: 90 percent / DIBAL-H / diethyl ether; toluene / 0.5 h / -78 °C

With 1H-imidazole; dmap; diisobutylaluminium hydride; triphenylphosphine; silver carbonate; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; toluene; benzene; 2: Mitsunobu reaction;
DOI:10.1021/jo0301550

Reference yield:

: 335163-22-9
(1'R,3R,5S)-3-hydroxy-5-(1'-methylbut-3'-enyl)dihydrofuran-2-one

: 335163-21-8
(1'R,3S,5S)-2-allyl-6-(tert-butyldiphenylsilanyloxy)benzoic acid 2-hydroxy-5-(1'-methylbut-3'-enyl)tetrahydrofuran-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / diethyl azodicarboxylate; Ph₃P / tetrahydrofuran / -78 - 20 °C

2: 98 percent / imidazole; DMAP / dimethylformamide / 5 h / 20 °C

3: 90 percent / DIBAL-H / diethyl ether; toluene / 0.5 h / -78 °C

With 1H-imidazole; dmap; diisobutylaluminium hydride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide; toluene; 1: Mitsunobu reaction;
DOI:10.1021/jo0301550