(8R,5Z)-((2R,3S)-1-(tert-Butyldiphenylsilyloxy)-3-hydroxypent-4-en-2-yl) 8-hydroxydeca-5,9-dienoate

Base Information

Chemical Name:(8R,5Z)-((2R,3S)-1-(tert-Butyldiphenylsilyloxy)-3-hydroxypent-4-en-2-yl) 8-hydroxydeca-5,9-dienoate
CAS No.:1330680-39-1
Molecular Formula:C₃₁H₄₂O₅Si
Molecular Weight:522.757
Hs Code.:

Synonyms:(8R,5Z)-((2R,3S)-1-(tert-Butyldiphenylsilyloxy)-3-hydroxypent-4-en-2-yl) 8-hydroxydeca-5,9-dienoate

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Chemical Property of (8R,5Z)-((2R,3S)-1-(tert-Butyldiphenylsilyloxy)-3-hydroxypent-4-en-2-yl) 8-hydroxydeca-5,9-dienoate

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Technology Process of (8R,5Z)-((2R,3S)-1-(tert-Butyldiphenylsilyloxy)-3-hydroxypent-4-en-2-yl) 8-hydroxydeca-5,9-dienoate

There total 17 articles about (8R,5Z)-((2R,3S)-1-(tert-Butyldiphenylsilyloxy)-3-hydroxypent-4-en-2-yl) 8-hydroxydeca-5,9-dienoate 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: 93.0%

: 1330680-38-0
(3R,5Z)-((2R,3S)-1-(tert-butyldiphenylsilyloxy)-3-(4-methoxybenzyloxy)pent-4-en-2-yl)-8-(4-methoxybenzyloxy)deca-5,9-dienoate

: 1330680-39-1
(8R,5Z)-((2R,3S)-1-(tert-Butyldiphenylsilyloxy)-3-hydroxypent-4-en-2-yl) 8-hydroxydeca-5,9-dienoate

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 0 - 20 ℃; for 2h; Inert atmosphere; aq. phosphate buffer;
DOI:10.1039/c1ob05335c

Reference yield:

: 954416-30-9
(4R)-4-((S)-1-(4-methoxybenzyloxy)allyl)-2,2-dimethyl-1,3-dioxolane

: 1330680-39-1
(8R,5Z)-((2R,3S)-1-(tert-Butyldiphenylsilyloxy)-3-hydroxypent-4-en-2-yl) 8-hydroxydeca-5,9-dienoate

Guidance literature:: Multi-step reaction with 4 steps

1: methanol; camphor-10-sulfonic acid / 2 h / 0 - 20 °C / Inert atmosphere

2: 1H-imidazole / tetrahydrofuran; dichloromethane / 3 h / 20 °C / Inert atmosphere

3: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 5 h / 0 °C / Inert atmosphere

4: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2 h / 0 - 20 °C / Inert atmosphere; aq. phosphate buffer

With 1H-imidazole; methanol; dmap; camphor-10-sulfonic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water;
DOI:10.1039/c1ob05335c

Reference yield:

: 954416-31-0
(2R,3S)-3-(4-methoxybenzyloxy)pent-4-ene-1,2-diol

: 1330680-39-1
(8R,5Z)-((2R,3S)-1-(tert-Butyldiphenylsilyloxy)-3-hydroxypent-4-en-2-yl) 8-hydroxydeca-5,9-dienoate

Guidance literature:: Multi-step reaction with 3 steps

1: 1H-imidazole / tetrahydrofuran; dichloromethane / 3 h / 20 °C / Inert atmosphere

2: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 5 h / 0 °C / Inert atmosphere

3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 2 h / 0 - 20 °C / Inert atmosphere; aq. phosphate buffer

With 1H-imidazole; dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water;
DOI:10.1039/c1ob05335c