(2S,3S,6S,8aR)-8a-Ethyl-6-hydroxymethyl-3-methoxymethyl-6-methyl-5-[(1E,3Z)-3-methyl-6-(2-methyl-[1,3]dioxolan-2-yl)-hexa-1,3-dienyl]-2-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ol

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Chemical Name:(2S,3S,6S,8aR)-8a-Ethyl-6-hydroxymethyl-3-methoxymethyl-6-methyl-5-[(1E,3Z)-3-methyl-6-(2-methyl-[1,3]dioxolan-2-yl)-hexa-1,3-dienyl]-2-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ol
CAS No.:228396-10-9
Molecular Formula:C₃₀H₄₅NO₆
Molecular Weight:515.69
Hs Code.:

(2S,3S,6S,8aR)-8a-Ethyl-6-hydroxymethyl-3-methoxymethyl-6-methyl-5-[(1E,3Z)-3-methyl-6-(2-methyl-[1,3]dioxolan-2-yl)-hexa-1,3-dienyl]-2-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ol

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Chemical Property of (2S,3S,6S,8aR)-8a-Ethyl-6-hydroxymethyl-3-methoxymethyl-6-methyl-5-[(1E,3Z)-3-methyl-6-(2-methyl-[1,3]dioxolan-2-yl)-hexa-1,3-dienyl]-2-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ol

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Technology Process of (2S,3S,6S,8aR)-8a-Ethyl-6-hydroxymethyl-3-methoxymethyl-6-methyl-5-[(1E,3Z)-3-methyl-6-(2-methyl-[1,3]dioxolan-2-yl)-hexa-1,3-dienyl]-2-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ol

There total 12 articles about (2S,3S,6S,8aR)-8a-Ethyl-6-hydroxymethyl-3-methoxymethyl-6-methyl-5-[(1E,3Z)-3-methyl-6-(2-methyl-[1,3]dioxolan-2-yl)-hexa-1,3-dienyl]-2-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ol 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:

: 101979-99-1
(2S,3S,8aR)-8a-Ethyl-3-hydroxymethyl-2-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-one

: 228396-10-9
(2S,3S,6S,8aR)-8a-Ethyl-6-hydroxymethyl-3-methoxymethyl-6-methyl-5-[(1E,3Z)-3-methyl-6-(2-methyl-[1,3]dioxolan-2-yl)-hexa-1,3-dienyl]-2-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ol

Guidance literature:: Multi-step reaction with 7 steps

2: n-BuLi

3: TBAF / tetrahydrofuran / Ambient temperature

4: 87 percent / s-BuLi / tetrahydrofuran / -78 °C

5: NaH

6: 85 percent / LiBH₄ / methanol; diethyl ether / 0 °C

7: 1.) t-BuLi / 1.) Et₂O, -78 deg C

With lithium borohydride; n-butyllithium; tetrabutyl ammonium fluoride; tert.-butyl lithium; sec.-butyllithium; sodium hydride; In tetrahydrofuran; methanol; diethyl ether;
DOI:10.1016/S0040-4039(99)00454-2

Reference yield:

: 228396-09-6
(Z)-(5-bromo-3-methylpent-3-en-1-yn-1-yl)trimethylsilane

: 228396-10-9
(2S,3S,6S,8aR)-8a-Ethyl-6-hydroxymethyl-3-methoxymethyl-6-methyl-5-[(1E,3Z)-3-methyl-6-(2-methyl-[1,3]dioxolan-2-yl)-hexa-1,3-dienyl]-2-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ol

Guidance literature:: Multi-step reaction with 6 steps

1: NaH

2: NaCl / dimethylsulfoxide; H₂O / 190 °C

3: pTSA

4: NaOH / tetrahydrofuran

5: 1.) Cp₂ZrHCl; 2.) NBS / 1.) THF

6: 1.) t-BuLi / 1.) Et₂O, -78 deg C

With sodium hydroxide; N-Bromosuccinimide; Schwartz's reagent; tert.-butyl lithium; sodium hydride; toluene-4-sulfonic acid; sodium chloride; In tetrahydrofuran; water; dimethyl sulfoxide;
DOI:10.1016/S0040-4039(99)00454-2

Reference yield:

: (Z)-6-Methyl-8-trimethylsilanyl-oct-5-en-7-yn-2-one

: 228396-10-9
(2S,3S,6S,8aR)-8a-Ethyl-6-hydroxymethyl-3-methoxymethyl-6-methyl-5-[(1E,3Z)-3-methyl-6-(2-methyl-[1,3]dioxolan-2-yl)-hexa-1,3-dienyl]-2-phenyl-hexahydro-oxazolo[3,2-a]pyridin-5-ol

Guidance literature:: Multi-step reaction with 4 steps

1: pTSA

2: NaOH / tetrahydrofuran

3: 1.) Cp₂ZrHCl; 2.) NBS / 1.) THF

4: 1.) t-BuLi / 1.) Et₂O, -78 deg C

With sodium hydroxide; N-Bromosuccinimide; Schwartz's reagent; tert.-butyl lithium; toluene-4-sulfonic acid; In tetrahydrofuran;
DOI:10.1016/S0040-4039(99)00454-2