(5R,8R,9S)-8-tert-butyldiphenylsiloxymethyl-9-methoxycarbonyl-9-trimethylsiloxy-1,7-dioxaspiro[4.4]non-3-ene-2,6-dione

Base Information

Chemical Name:(5R,8R,9S)-8-tert-butyldiphenylsiloxymethyl-9-methoxycarbonyl-9-trimethylsiloxy-1,7-dioxaspiro[4.4]non-3-ene-2,6-dione
CAS No.:215173-32-3
Molecular Formula:C₂₉H₃₆O₈Si₂
Molecular Weight:568.771
Hs Code.:

Synonyms:(5R,8R,9S)-8-tert-butyldiphenylsiloxymethyl-9-methoxycarbonyl-9-trimethylsiloxy-1,7-dioxaspiro[4.4]non-3-ene-2,6-dione

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Chemical Property of (5R,8R,9S)-8-tert-butyldiphenylsiloxymethyl-9-methoxycarbonyl-9-trimethylsiloxy-1,7-dioxaspiro[4.4]non-3-ene-2,6-dione

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Technology Process of (5R,8R,9S)-8-tert-butyldiphenylsiloxymethyl-9-methoxycarbonyl-9-trimethylsiloxy-1,7-dioxaspiro[4.4]non-3-ene-2,6-dione

There total 11 articles about (5R,8R,9S)-8-tert-butyldiphenylsiloxymethyl-9-methoxycarbonyl-9-trimethylsiloxy-1,7-dioxaspiro[4.4]non-3-ene-2,6-dione 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: 54.0%

: 75-77-4
chloro-trimethyl-silane

: 215173-30-1
methyl (3R)-4-tert-butyldiphenylsiloxy-3-(5-phenylthio-2-furoyloxy)-2-oxobutanoate

: 215173-32-3
(5R,8R,9S)-8-tert-butyldiphenylsiloxymethyl-9-methoxycarbonyl-9-trimethylsiloxy-1,7-dioxaspiro[4.4]non-3-ene-2,6-dione

Guidance literature:: Multistep reaction.;
DOI:10.1021/jo011157s

Reference yield:

: 13171-64-7
Dimethyl D-tartrate

: 215173-32-3
(5R,8R,9S)-8-tert-butyldiphenylsiloxymethyl-9-methoxycarbonyl-9-trimethylsiloxy-1,7-dioxaspiro[4.4]non-3-ene-2,6-dione

Guidance literature:: Multi-step reaction with 7 steps

1.1: 62 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 72 h

2.1: BH₃*SMe₂ / tetrahydrofuran / 2 h / 20 °C

2.2: NaBH₄ / tetrahydrofuran / 2 h / 0 - 20 °C

3.1: 1.30 g / imidazole / CH₂Cl₂ / 1 h / 0 °C

4.1: 96 percent / dicyclohexylcarbodiimide; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 5 h / 20 °C

5.1: 95 percent / Me₂AlCl / CH₂Cl₂; various solvent(s) / 4 h / -25 - 20 °C

6.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 20 °C

With 1H-imidazole; dmap; dimethylsulfide borane complex; dimethylaluminum chloride; pyridinium p-toluenesulfonate; Dess-Martin periodane; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 6.1: Dess-Martin oxidation;
DOI:10.1021/jo011157s

Reference yield:

: 93499-95-7,102573-08-0
(2S,3R)-3,4-Dihydroxy-2-(tetrahydro-pyran-2-yloxy)-butyric acid methyl ester

: 215173-32-3
(5R,8R,9S)-8-tert-butyldiphenylsiloxymethyl-9-methoxycarbonyl-9-trimethylsiloxy-1,7-dioxaspiro[4.4]non-3-ene-2,6-dione

Guidance literature:: Multi-step reaction with 5 steps

1: 1.30 g / imidazole / CH₂Cl₂ / 1 h / 0 °C

2: 96 percent / dicyclohexylcarbodiimide; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 5 h / 20 °C

3: 95 percent / Me₂AlCl / CH₂Cl₂; various solvent(s) / 4 h / -25 - 20 °C

4: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 20 °C

With 1H-imidazole; dmap; dimethylaluminum chloride; Dess-Martin periodane; dicyclohexyl-carbodiimide; In dichloromethane; 4: Dess-Martin oxidation;
DOI:10.1021/jo011157s