(4R,5S,E)-((2S,3R,E)-6-(allyloxy)-3-((2-methoxyethoxy)methoxy)-6-oxohex-4-en-2-yl) 5-((S)-3-(4-methoxybenzyloxy)butanoyloxy)-4-((2-methoxyethoxy)methoxy)hex-2-enoate

Base Information

Chemical Name:(4R,5S,E)-((2S,3R,E)-6-(allyloxy)-3-((2-methoxyethoxy)methoxy)-6-oxohex-4-en-2-yl) 5-((S)-3-(4-methoxybenzyloxy)butanoyloxy)-4-((2-methoxyethoxy)methoxy)hex-2-enoate
CAS No.:861902-88-7
Molecular Formula:C₃₅H₅₂O₁₄
Molecular Weight:696.789
Hs Code.:

(4R,5S,E)-((2S,3R,E)-6-(allyloxy)-3-((2-methoxyethoxy)methoxy)-6-oxohex-4-en-2-yl) 5-((S)-3-(4-methoxybenzyloxy)butanoyloxy)-4-((2-methoxyethoxy)methoxy)hex-2-enoate

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Chemical Property of (4R,5S,E)-((2S,3R,E)-6-(allyloxy)-3-((2-methoxyethoxy)methoxy)-6-oxohex-4-en-2-yl) 5-((S)-3-(4-methoxybenzyloxy)butanoyloxy)-4-((2-methoxyethoxy)methoxy)hex-2-enoate

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Technology Process of (4R,5S,E)-((2S,3R,E)-6-(allyloxy)-3-((2-methoxyethoxy)methoxy)-6-oxohex-4-en-2-yl) 5-((S)-3-(4-methoxybenzyloxy)butanoyloxy)-4-((2-methoxyethoxy)methoxy)hex-2-enoate

There total 7 articles about (4R,5S,E)-((2S,3R,E)-6-(allyloxy)-3-((2-methoxyethoxy)methoxy)-6-oxohex-4-en-2-yl) 5-((S)-3-(4-methoxybenzyloxy)butanoyloxy)-4-((2-methoxyethoxy)methoxy)hex-2-enoate 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:

: 861902-90-1
(E,3R,4S)-4-(4-methoxybenzyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)pent-1-en-3-ol

: 861902-88-7
(4R,5S,E)-((2S,3R,E)-6-(allyloxy)-3-((2-methoxyethoxy)methoxy)-6-oxohex-4-en-2-yl) 5-((S)-3-(4-methoxybenzyloxy)butanoyloxy)-4-((2-methoxyethoxy)methoxy)hex-2-enoate

Guidance literature:: Multi-step reaction with 5 steps

1: iPr₂NEt / CH₂Cl₂ / 41 h / 20 °C

2: 76 mg / HCl / H₂O; tetrahydrofuran / 0.17 h / 20 °C

3: 92 percent / DCC; DMAP; CSA / CH₂Cl₂ / 11 h / 20 °C

4: 88 percent / DDQ; phosphate buffer / CH₂Cl₂ / 3 h / 20 °C / pH 7.2

5: 88 percent / EDCI; DMAP / CH₂Cl₂ / 13 h / 20 °C

With hydrogenchloride; dmap; phosphate buffer; camphor-10-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol0508429

Reference yield:

: 861902-94-5
(S,E)-4-(4-methoxybenzyloxy)-1-(4-methyl-2,6,7-trioxabicyclo[2.2.2]octan-1-yl)pent-1-en-3-one

: 861902-88-7
(4R,5S,E)-((2S,3R,E)-6-(allyloxy)-3-((2-methoxyethoxy)methoxy)-6-oxohex-4-en-2-yl) 5-((S)-3-(4-methoxybenzyloxy)butanoyloxy)-4-((2-methoxyethoxy)methoxy)hex-2-enoate

Guidance literature:: Multi-step reaction with 6 steps

1: 91 percent / LiEt₃BH / tetrahydrofuran; CH₂Cl₂ / 0.17 h / -78 °C

2: iPr₂NEt / CH₂Cl₂ / 41 h / 20 °C

3: 76 mg / HCl / H₂O; tetrahydrofuran / 0.17 h / 20 °C

4: 92 percent / DCC; DMAP; CSA / CH₂Cl₂ / 11 h / 20 °C

5: 88 percent / DDQ; phosphate buffer / CH₂Cl₂ / 3 h / 20 °C / pH 7.2

6: 88 percent / EDCI; DMAP / CH₂Cl₂ / 13 h / 20 °C

With hydrogenchloride; dmap; phosphate buffer; camphor-10-sulfonic acid; lithium triethylborohydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ol0508429

Reference yield:

: 861902-95-6
(E,4R,5S)-4-((2-methoxyethoxy)methoxy)-5-(4-methoxybenzyloxy)hex-2-enoic acid

: 861902-88-7
(4R,5S,E)-((2S,3R,E)-6-(allyloxy)-3-((2-methoxyethoxy)methoxy)-6-oxohex-4-en-2-yl) 5-((S)-3-(4-methoxybenzyloxy)butanoyloxy)-4-((2-methoxyethoxy)methoxy)hex-2-enoate

Guidance literature:: Multi-step reaction with 3 steps

1: 92 percent / DCC; DMAP; CSA / CH₂Cl₂ / 11 h / 20 °C

2: 88 percent / DDQ; phosphate buffer / CH₂Cl₂ / 3 h / 20 °C / pH 7.2

3: 88 percent / EDCI; DMAP / CH₂Cl₂ / 13 h / 20 °C

With dmap; phosphate buffer; camphor-10-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dicyclohexyl-carbodiimide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane;
DOI:10.1021/ol0508429