(3S,5S)-3-tert-butyldimethylsilyloxy-5-hydroxy-8-[2-phenyl-4-(R)-(triphenylmethyloxy)methyl-1,3-dioxan-6(S)-yl]-octan-7-on-1-oic acid-2(S)-napthylethanol ester

Base Information

Chemical Name:(3S,5S)-3-tert-butyldimethylsilyloxy-5-hydroxy-8-[2-phenyl-4-(R)-(triphenylmethyloxy)methyl-1,3-dioxan-6(S)-yl]-octan-7-on-1-oic acid-2(S)-napthylethanol ester
CAS No.:203454-79-9
Molecular Formula:C₅₆H₆₄O₈Si
Molecular Weight:893.205
Hs Code.:

(3S,5S)-3-tert-butyldimethylsilyloxy-5-hydroxy-8-[2-phenyl-4-(R)-(triphenylmethyloxy)methyl-1,3-dioxan-6(S)-yl]-octan-7-on-1-oic acid-2(S)-napthylethanol ester

Synonyms:(3S,5S)-3-tert-butyldimethylsilyloxy-5-hydroxy-8-[2-phenyl-4-(R)-(triphenylmethyloxy)methyl-1,3-dioxan-6(S)-yl]-octan-7-on-1-oic acid-2(S)-napthylethanol ester

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Chemical Property of (3S,5S)-3-tert-butyldimethylsilyloxy-5-hydroxy-8-[2-phenyl-4-(R)-(triphenylmethyloxy)methyl-1,3-dioxan-6(S)-yl]-octan-7-on-1-oic acid-2(S)-napthylethanol ester

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Technology Process of (3S,5S)-3-tert-butyldimethylsilyloxy-5-hydroxy-8-[2-phenyl-4-(R)-(triphenylmethyloxy)methyl-1,3-dioxan-6(S)-yl]-octan-7-on-1-oic acid-2(S)-napthylethanol ester

There total 8 articles about (3S,5S)-3-tert-butyldimethylsilyloxy-5-hydroxy-8-[2-phenyl-4-(R)-(triphenylmethyloxy)methyl-1,3-dioxan-6(S)-yl]-octan-7-on-1-oic acid-2(S)-napthylethanol 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: 80.0%

: 139278-09-4
(S)-1-(2-naphthyl)ethyl (3S)-4-formyl-3-(tert-butyldimethylsiloxy)butanoate

: 187819-45-0
[2R,4S,6S]-4-(propan-2-one)-6-[(2-triphenylmethyloxy)-ethyl]-2-phenyl-1,3-dioxane

: 203454-79-9
(3S,5S)-3-tert-butyldimethylsilyloxy-5-hydroxy-8-[2-phenyl-4-(R)-(triphenylmethyloxy)methyl-1,3-dioxan-6(S)-yl]-octan-7-on-1-oic acid-2(S)-napthylethanol ester

: (3S,5S)-3-tert-butyldimethylsilyloxy-5-hydroxy-8-[2-phenyl-4-(R)-(triphenylmethyloxy)methyl-1,3-dioxan-6(S)-yl]-octan-7-on-1-oic acid-2(S)-napthylethanol ester

Guidance literature:: With di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In diethyl ether; at -78 ℃; for 0.5h; Title compound not separated from byproducts;
DOI:10.1021/ja027640h

Reference yield:

: 139278-09-4
(S)-1-(2-naphthyl)ethyl (3S)-4-formyl-3-(tert-butyldimethylsiloxy)butanoate

: C₄₁H₄₉BO₄

: (1S)-1-(2-naphthyl)ethyl (3S,5R)-3-tert-butyldimethylsilyloxy-5-hydroxy-8-[2-phenyl-4(R)-(triphenylmethyloxy)-methyl-1,3-dioxan-6-(S)-yl]-octan-7-on-1-oate

: 203454-79-9
(3S,5S)-3-tert-butyldimethylsilyloxy-5-hydroxy-8-[2-phenyl-4-(R)-(triphenylmethyloxy)methyl-1,3-dioxan-6(S)-yl]-octan-7-on-1-oic acid-2(S)-napthylethanol ester

Guidance literature:: In diethyl ether; at -78 ℃; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
DOI:10.1021/jo962417m

Reference yield:

: 65291-30-7
(R)-(+)-trityl glycidyl ether

: 203454-79-9
(3S,5S)-3-tert-butyldimethylsilyloxy-5-hydroxy-8-[2-phenyl-4-(R)-(triphenylmethyloxy)methyl-1,3-dioxan-6(S)-yl]-octan-7-on-1-oic acid-2(S)-napthylethanol ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: CuI / tetrahydrofuran / 1 h / -78 °C

1.2: 32.54 g / tetrahydrofuran / 1.5 h / -78 °C

2.1: O₃ / CH₂Cl₂ / 0.67 h / -78 °C

2.2: PPh₃ / CH₂Cl₂ / 5 h / 20 °C

2.3: 73 percent / CH₂Cl₂ / 14 h / 20 °C

3.1: 76 percent / t-BuOK / tetrahydrofuran / 2.5 h / 0 °C

4.1: 81 percent / diethyl ether / 1.5 h / -78 °C

5.1: Hunig's base / diethyl ether / 0.75 h / -78 °C

6.1: diethyl ether

With copper(l) iodide; potassium tert-butylate; ozone; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; 1.1: Metallation / 1.2: Condensation / 2.1: Oxidation / 2.2: Reduction / 2.3: Condensation / 3.1: Addition / 4.1: Methylation / 5.1: Substitution / 6.1: Condensation;
DOI:10.1016/S0040-4020(99)00438-X