(E)-1-[(2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5-methyltetrahydropyran-2-yl]-6-methylhept-3-en-2-one

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Chemical Name:(E)-1-[(2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5-methyltetrahydropyran-2-yl]-6-methylhept-3-en-2-one
CAS No.:617715-00-1
Molecular Formula:C₄₉H₇₀O₇Si
Molecular Weight:799.176
Hs Code.:

(E)-1-[(2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5-methyltetrahydropyran-2-yl]-6-methylhept-3-en-2-one

Synonyms:(E)-1-[(2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5-methyltetrahydropyran-2-yl]-6-methylhept-3-en-2-one

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Chemical Property of (E)-1-[(2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5-methyltetrahydropyran-2-yl]-6-methylhept-3-en-2-one

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Technology Process of (E)-1-[(2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5-methyltetrahydropyran-2-yl]-6-methylhept-3-en-2-one

There total 9 articles about (E)-1-[(2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5-methyltetrahydropyran-2-yl]-6-methylhept-3-en-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: 75.0%

: 617715-15-8
(E)-1-[(2S,5S,6R)-6-((S)-3-{(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-[2-(4-methoxy-benzyloxy)-ethyl]-tetrahydro-pyran-2-yl}-2-methoxy-propyl)-5-methyl-tetrahydro-pyran-2-yl]-6-methyl-hept-3-en-2-ol

: 617715-00-1
(E)-1-[(2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5-methyltetrahydropyran-2-yl]-6-methylhept-3-en-2-one

Guidance literature:: With sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane;
DOI:10.1002/anie.200351817

Reference yield:

: 617714-99-5
2-[(2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5-methyltetrahydropyran-2-yl]acetaldehyde

: 617715-00-1
(E)-1-[(2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5-methyltetrahydropyran-2-yl]-6-methylhept-3-en-2-one

Guidance literature:: Multi-step reaction with 2 steps

1.1: Cp₂Zr(H)Cl / CH₂Cl₂ / 20 °C

1.2: dimethylzinc / CH₂Cl₂ / -78 °C

1.3: 87 percent / CH₂Cl₂ / 1 h / -78 - 0 °C

2.1: 75 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

With Schwartz's reagent; sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; 2.1: Dess-Martin oxidation;
DOI:10.1002/anie.200351817

Reference yield:

: 617714-97-3
(2R,6S)-2-[(2S,5S,8S)-8,10-bis-(tert-butyldimethylsilanyloxy)-2-methoxy-5-methyl-4-oxodecyl]-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-4-one

: 617715-00-1
(E)-1-[(2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5-methyltetrahydropyran-2-yl]-6-methylhept-3-en-2-one

Guidance literature:: Multi-step reaction with 9 steps

1.1: 84 percent / lithium tri-sec-butylborohydride / tetrahydrofuran / 1.5 h / -78 °C

2.1: 73 percent / imidazole / dimethylformamide / 40 h

3.1: 95 percent / LiAlH₄; (-)-N-methylephedrine; N-ethylaniline / diethyl ether / 2 h / -78 °C

4.1: 100 percent / pyridine / CH₂Cl₂

5.1: 84 percent / HF*pyridine; pyridine / tetrahydrofuran

6.1: 73 percent / sodium hydride / benzene / 16 h / 60 °C

7.1: 95 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

8.1: Cp₂Zr(H)Cl / CH₂Cl₂ / 20 °C

8.2: dimethylzinc / CH₂Cl₂ / -78 °C

8.3: 87 percent / CH₂Cl₂ / 1 h / -78 - 0 °C

9.1: 75 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

With pyridine; 1H-imidazole; lithium aluminium tetrahydride; Schwartz's reagent; (-)-N-methylephedrine; L-Selectride; sodium hydride; sodium hydrogencarbonate; Dess-Martin periodane; pyridine hydrogenfluoride; N-ethyl-N-phenylamine; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide; benzene; 3.1: Terashima reduction / 7.1: Dess-Martin oxidation / 9.1: Dess-Martin oxidation;
DOI:10.1002/anie.200351817