acetic acid (R)-(E)-1-((2S,5S,6R)-6-((S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-(2-hydroxyethyl)tetrahydropyran-2-yl]-2-methoxypropyl)-5-methyltetrahydropyran-2-ylmethyl)-5-methylhex-2-enyl ester

Base Information

Chemical Name:acetic acid (R)-(E)-1-((2S,5S,6R)-6-((S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-(2-hydroxyethyl)tetrahydropyran-2-yl]-2-methoxypropyl)-5-methyltetrahydropyran-2-ylmethyl)-5-methylhex-2-enyl ester
CAS No.:617715-16-9
Molecular Formula:C₄₃H₆₆O₇Si
Molecular Weight:723.078
Hs Code.:

acetic acid (R)-(E)-1-((2S,5S,6R)-6-((S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-(2-hydroxyethyl)tetrahydropyran-2-yl]-2-methoxypropyl)-5-methyltetrahydropyran-2-ylmethyl)-5-methylhex-2-enyl ester

Synonyms:acetic acid (R)-(E)-1-((2S,5S,6R)-6-((S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-(2-hydroxyethyl)tetrahydropyran-2-yl]-2-methoxypropyl)-5-methyltetrahydropyran-2-ylmethyl)-5-methylhex-2-enyl ester

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Chemical Property of acetic acid (R)-(E)-1-((2S,5S,6R)-6-((S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-(2-hydroxyethyl)tetrahydropyran-2-yl]-2-methoxypropyl)-5-methyltetrahydropyran-2-ylmethyl)-5-methylhex-2-enyl ester

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Technology Process of acetic acid (R)-(E)-1-((2S,5S,6R)-6-((S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-(2-hydroxyethyl)tetrahydropyran-2-yl]-2-methoxypropyl)-5-methyltetrahydropyran-2-ylmethyl)-5-methylhex-2-enyl ester

There total 12 articles about acetic acid (R)-(E)-1-((2S,5S,6R)-6-((S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-(2-hydroxyethyl)tetrahydropyran-2-yl]-2-methoxypropyl)-5-methyltetrahydropyran-2-ylmethyl)-5-methylhex-2-enyl ester 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: 100.0%

: 617715-02-3
acetic acid (R,E)-1-((2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilyloxy)-6-(2-(4-methoxybenzyloxy)ethyl)tetrahydro-2H-pyran-2-yl)-2-methoxypropyl)-5-methyltetrahydro-2H-pyran-2-yl)-6-methylhept-3-en-2-yl ester

: 617715-16-9
acetic acid (R)-(E)-1-((2S,5S,6R)-6-((S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-(2-hydroxyethyl)tetrahydropyran-2-yl]-2-methoxypropyl)-5-methyltetrahydropyran-2-ylmethyl)-5-methylhex-2-enyl ester

Guidance literature:: With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In phosphate buffer; dichloromethane; tert-butyl alcohol; for 1.5h; pH=7;
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

: 617715-16-9
acetic acid (R)-(E)-1-((2S,5S,6R)-6-((S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-(2-hydroxyethyl)tetrahydropyran-2-yl]-2-methoxypropyl)-5-methyltetrahydropyran-2-ylmethyl)-5-methylhex-2-enyl ester

Guidance literature:: Multi-step reaction with 6 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

5.1: 97 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂

6.1: 100 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; aq. phosphate buffer; 2-methyl-propan-2-ol / 1.5 h / pH 7

With pyridine; dmap; Schwartz's reagent; borane-THF; (R)-2-methyl-oxazaborolidine; sodium hydrogencarbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In phosphate buffer; dichloromethane; tert-butyl alcohol; 1.1: Dess-Martin oxidation / 3.1: Dess-Martin oxidation / 4.1: Corey-Bakshi-Shibata borohydride reduction;
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

: 617715-16-9
acetic acid (R)-(E)-1-((2S,5S,6R)-6-((S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-(2-hydroxyethyl)tetrahydropyran-2-yl]-2-methoxypropyl)-5-methyltetrahydropyran-2-ylmethyl)-5-methylhex-2-enyl ester

Guidance literature:: Multi-step reaction with 5 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

4.1: 97 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂

5.1: 100 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; aq. phosphate buffer; 2-methyl-propan-2-ol / 1.5 h / pH 7

With pyridine; dmap; Schwartz's reagent; borane-THF; (R)-2-methyl-oxazaborolidine; sodium hydrogencarbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In phosphate buffer; dichloromethane; tert-butyl alcohol; 2.1: Dess-Martin oxidation / 3.1: Corey-Bakshi-Shibata borohydride reduction;
DOI:10.1002/anie.200351817