(E)-(R)-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-ol

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Chemical Name:(E)-(R)-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-ol
CAS No.:617715-01-2
Molecular Formula:C₄₉H₇₂O₇Si
Molecular Weight:801.192
Hs Code.:

(E)-(R)-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-ol

Synonyms:(E)-(R)-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-ol

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Chemical Property of (E)-(R)-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-ol

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Technology Process of (E)-(R)-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-ol

There total 10 articles about (E)-(R)-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-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: 65.0%

: 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

: (E)-(S)-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-ol

: 617715-01-2
(E)-(R)-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-ol

Guidance literature:: (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; With borane-THF; (S)-1-methyl-3,3-diphenyl-hexahydropyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; toluene; at -10 ℃; for 0.166667h;

With water; In tetrahydrofuran; toluene; at -10 - 20 ℃; for 0.166667h; optical yield given as %de;
DOI:10.1016/j.tet.2011.05.020

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

: 617715-01-2
(E)-(R)-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-ol

Guidance literature:: Multi-step reaction with 3 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

3.1: (S)-2-methyloxazaborolidine; borane-tetrahydrofuran complex / -10 °C

With Schwartz's reagent; borane-THF; (R)-2-methyl-oxazaborolidine; sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; 2.1: Dess-Martin oxidation / 3.1: Corey-Bakshi-Shibata borohydride reduction;
DOI:10.1002/anie.200351817

Reference yield:

: 617715-14-7
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]-ethanol

: 617715-01-2
(E)-(R)-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-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 95 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

2.1: Cp₂Zr(H)Cl / CH₂Cl₂ / 20 °C

2.2: dimethylzinc / CH₂Cl₂ / -78 °C

2.3: 87 percent / CH₂Cl₂ / 1 h / -78 - 0 °C

3.1: 75 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

4.1: (S)-2-methyloxazaborolidine; borane-tetrahydrofuran complex / -10 °C

With Schwartz's reagent; borane-THF; (R)-2-methyl-oxazaborolidine; sodium hydrogencarbonate; Dess-Martin periodane; In dichloromethane; 1.1: Dess-Martin oxidation / 3.1: Dess-Martin oxidation / 4.1: Corey-Bakshi-Shibata borohydride reduction;
DOI:10.1002/anie.200351817