(6R,10S,E)-6-(tert-butyldiphenylsilyloxy)-10-propyl-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one

Base Information

Chemical Name:(6R,10S,E)-6-(tert-butyldiphenylsilyloxy)-10-propyl-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one
CAS No.:1372609-34-1
Molecular Formula:C₂₈H₃₈O₃Si
Molecular Weight:450.693
Hs Code.:

Synonyms:(6R,10S,E)-6-(tert-butyldiphenylsilyloxy)-10-propyl-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one

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Chemical Property of (6R,10S,E)-6-(tert-butyldiphenylsilyloxy)-10-propyl-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one

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Technology Process of (6R,10S,E)-6-(tert-butyldiphenylsilyloxy)-10-propyl-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one

There total 8 articles about (6R,10S,E)-6-(tert-butyldiphenylsilyloxy)-10-propyl-3,4,5,6,9,10-hexahydro-2H-oxecin-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: 59.0%

: 1372609-33-0
(S)-hept-1-en-4-yl (R)-5-(tert-butyldiphenylsilyloxy)hept-6-enoate

: (6R,10S,Z)-6-(tert-butyldiphenylsilyloxy)-10-propyl-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one

: 1372609-34-1
(6R,10S,E)-6-(tert-butyldiphenylsilyloxy)-10-propyl-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one

Guidance literature:: With Grubbs catalyst first generation; In dichloromethane; at 55 ℃; for 22h; optical yield given as %de; stereoselective reaction;
DOI:10.1002/ejoc.201101601

Reference yield:

: 1373131-81-7
(R)-5-(tert-butyldiphenylsilyloxy)hept-6-enoic acid

: (6R,10S,Z)-6-(tert-butyldiphenylsilyloxy)-10-propyl-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one

: 1372609-34-1
(6R,10S,E)-6-(tert-butyldiphenylsilyloxy)-10-propyl-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one

Guidance literature:: Multi-step reaction with 2 steps

1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 8.17 h / 0 - 20 °C

2: Grubbs catalyst first generation / dichloromethane / 22 h / 55 °C

With Grubbs catalyst first generation; dmap; dicyclohexyl-carbodiimide; In dichloromethane;
DOI:10.1002/ejoc.201101601

Reference yield:

: 111-29-5
1 ,5-pentanediol

: (6R,10S,Z)-6-(tert-butyldiphenylsilyloxy)-10-propyl-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one

: 1372609-34-1
(6R,10S,E)-6-(tert-butyldiphenylsilyloxy)-10-propyl-3,4,5,6,9,10-hexahydro-2H-oxecin-2-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: sodium hydride / tetrahydrofuran / 0.17 h / 0 °C

1.2: 4 h / 0 - 20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.5 h / -78 °C

2.2: 0.5 h / 0 °C

3.1: tetrahydrofuran / 2 h / 0 - 20 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: titanium(IV) isopropylate; diethyl (2R,3R)-tartrate / dichloromethane / 0.5 h / -20 °C / Molecular sieve

4.2: 5 h / -20 °C / Molecular sieve

5.1: 1H-imidazole / dichloromethane / 2 h / 0 - 20 °C

6.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 4 h / Reflux

7.1: dipyridinium dichromate / N,N-dimethyl-formamide / 10 h / 20 °C

8.1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 8.17 h / 0 - 20 °C

9.1: Grubbs catalyst first generation / dichloromethane / 22 h / 55 °C

With 1H-imidazole; Grubbs catalyst first generation; titanium(IV) isopropylate; dmap; dipyridinium dichromate; oxalyl dichloride; diethyl (2R,3R)-tartrate; water; sodium hydride; dimethyl sulfoxide; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2.1: Swern oxidation / 2.2: Swern oxidation;
DOI:10.1002/ejoc.201101601