cis-1-<(2R,3aR,4R,5R,6aS)-5-(<(1,1-dimethylethyl)dimethylsilyl>oxy)-2-ethoxyhexahydro-2H-cyclopentafuran-4-yl>-1-octene-3-one

Base Information

• Chemical Name: cis-1-<(2R,3aR,4R,5R,6aS)-5-(<(1,1-dimethylethyl)dimethylsilyl>oxy)-2-ethoxyhexahydro-2H-cyclopentafuran-4-yl>-1-octene-3-one
• CAS No.: 130608-88-7
• Molecular Formula: C₂₃H₄₂O₄Si
• Molecular Weight: 410.67
• Mol file: 130608-88-7.mol

Synonyms:cis-1-<(2R,3aR,4R,5R,6aS)-5-(<(1,1-dimethylethyl)dimethylsilyl>oxy)-2-ethoxyhexahydro-2H-cyclopentafuran-4-yl>-1-octene-3-one

Chemical Property of cis-1-<(2R,3aR,4R,5R,6aS)-5-(<(1,1-dimethylethyl)dimethylsilyl>oxy)-2-ethoxyhexahydro-2H-cyclopentafuran-4-yl>-1-octene-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of cis-1-<(2R,3aR,4R,5R,6aS)-5-(<(1,1-dimethylethyl)dimethylsilyl>oxy)-2-ethoxyhexahydro-2H-cyclopentafuran-4-yl>-1-octene-3-one

There total 1 articles about cis-1-<(2R,3aR,4R,5R,6aS)-5-(<(1,1-dimethylethyl)dimethylsilyl>oxy)-2-ethoxyhexahydro-2H-cyclopentafuran-4-yl>-1-octene-3-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: 12.0%

oct-1-yn-3-one (27593-19-7) + (1,1-dimethylethyl) (<(1R,4S)-4-(1-ethoxy-2-bromoethoxy)-2-cyclopentene-1-yl>oxy)dimethylsilane (130513-23-4) → 1,3,5-tri(hexane-1-one-1-yl)benzene (14269-14-8) + cis-1-<(2R,3aR,4R,5R,6aS)-5-(<(1,1-dimethylethyl)dimethylsilyl>oxy)-2-ethoxyhexahydro-2H-cyclopentafuran-4-yl>-1-octene-3-one (130608-88-7) + trans-1-<(2R,3aR,4R,5R,6aS)-5-(<(1,1-dimethylethyl)dimethylsilyl>oxy)-2-ethoxyhexahydro-2H-cyclopentafuran-4-yl>-1-octene-3-one (130607-55-5) + trans-1-<(2S,3aR,4R,5R,6aS)-5-(<(1,1-dimethylethyl)dimethylsilyl>oxy)-2-ethoxyhexahydro-2H-cyclopentafuran-4-yl>-1-octene-3-one (130607-56-6)

Guidance literature:

hydroxocobalamine hydrochloride; In N,N-dimethyl-formamide; for 44h; Further byproducts given; Irradiation; electrolysis in 0.3M LiClO₄ at 0.9V;

DOI:10.1016/S0040-4020(01)85455-7

Reference yield:

(E)-1-[(3aR,4R,5R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-2-ethoxy-hexahydro-cyclopenta[b]furan-4-yl]-oct-1-en-3-one (104015-24-9,108741-24-8,108741-25-9,130607-55-5,130607-56-6,130607-57-7,130608-88-7,136235-16-0,136235-17-1) → prostaglandin F2α (37658-84-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / (S)-BINAl-H / tetrahydrofuran / -100 °C

2: 98 percent / 1.5percent aqueous hydrochloric acid / tetrahydrofuran / Ambient temperature

3: 62 percent / potassium tert-butoxide / tetrahydrofuran / Ambient temperature

With hydrogenchloride; (-)-(S)-BINAL-H; potassium tert-butylate; In tetrahydrofuran;

DOI:10.1021/ja00280a043

Reference yield:

(E)-1-[(3aR,4R,5R,6aS)-5-(tert-Butyl-dimethyl-silanyloxy)-2-ethoxy-hexahydro-cyclopenta[b]furan-4-yl]-oct-1-en-3-one (104015-24-9,108741-24-8,108741-25-9,130607-55-5,130607-56-6,130607-57-7,130608-88-7,136235-16-0,136235-17-1) → (3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol (51388-75-1,59829-49-1,59829-50-4,59829-51-5,59829-52-6,85550-76-1,85550-82-9,136235-23-9,136235-24-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / (S)-BINAl-H / tetrahydrofuran / -100 °C

2: 98 percent / 1.5percent aqueous hydrochloric acid / tetrahydrofuran / Ambient temperature

With hydrogenchloride; (-)-(S)-BINAL-H; In tetrahydrofuran;

DOI:10.1021/ja00280a043

upstream raw materials:

oct-1-yn-3-one

(1,1-dimethylethyl) (<(1R,4S)-4-(1-ethoxy-2-bromoethoxy)-2-cyclopentene-1-yl>oxy)dimethylsilane

Downstream raw materials:

prostaglandin F_2α

(3aR,4R,5R,6a5)-4-[(E,3S)-3-Hydroxy-1-octenyl]perhydrocyclopenta[b]fura n-2,5-diol