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

Base Information

Chemical Name:(1S)-1-(2-naphthyl)ethyl (3S,5S)-3-tert-butyldimethylsilyloxy-5-methoxy-8-[2-phenyl-4(R)-(triphenylmethyloxy)-methyl-1,3-dioxan-6-(S)-yl]-octan-7-on-1-oate
CAS No.:203454-81-3
Molecular Formula:C₅₇H₆₆O₈Si
Molecular Weight:907.232
Hs Code.:

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

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

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

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

There total 8 articles about (1S)-1-(2-naphthyl)ethyl (3S,5S)-3-tert-butyldimethylsilyloxy-5-methoxy-8-[2-phenyl-4(R)-(triphenylmethyloxy)-methyl-1,3-dioxan-6-(S)-yl]-octan-7-on-1-oate 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: 91.0%

: 420-37-1
trimethoxonium tetrafluoroborate

: 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

: 203454-81-3
(1S)-1-(2-naphthyl)ethyl (3S,5S)-3-tert-butyldimethylsilyloxy-5-methoxy-8-[2-phenyl-4(R)-(triphenylmethyloxy)-methyl-1,3-dioxan-6-(S)-yl]-octan-7-on-1-oate

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; In dichloromethane; at 20 ℃; for 0.833333h;
DOI:10.1016/S0040-4020(99)00438-X

Reference yield:

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

: 203454-81-3
(1S)-1-(2-naphthyl)ethyl (3S,5S)-3-tert-butyldimethylsilyloxy-5-methoxy-8-[2-phenyl-4(R)-(triphenylmethyloxy)-methyl-1,3-dioxan-6-(S)-yl]-octan-7-on-1-oate

Guidance literature:: Multi-step reaction with 2 steps

1: diethyl ether

2: 91 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 0.83 h / 20 °C

With 2,6-di-tert-butyl-4-methylpyridine; In diethyl ether; dichloromethane; 1: Condensation / 2: Methylation;
DOI:10.1016/S0040-4020(99)00438-X

Reference yield:

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

: 203454-81-3
(1S)-1-(2-naphthyl)ethyl (3S,5S)-3-tert-butyldimethylsilyloxy-5-methoxy-8-[2-phenyl-4(R)-(triphenylmethyloxy)-methyl-1,3-dioxan-6-(S)-yl]-octan-7-on-1-oate

Guidance literature:: Multi-step reaction with 7 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

7.1: 91 percent / 2,6-di-tert-butyl-4-methylpyridine / CH₂Cl₂ / 0.83 h / 20 °C

With copper(l) iodide; 2,6-di-tert-butyl-4-methylpyridine; 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 / 7.1: Methylation;
DOI:10.1016/S0040-4020(99)00438-X