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

Base Information

Chemical Name:(5R,8R,9S)-8-(tert-butyldiphenylsiloxymethyl)-9-hydroxy-9-methoxycarbonyl-1,7-dioxaspiro[4.4]non-3-ene-2,6-dione
CAS No.:215173-31-2
Molecular Formula:C₂₆H₂₈O₈Si
Molecular Weight:496.589
Hs Code.:

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

There total 12 articles about (5R,8R,9S)-8-(tert-butyldiphenylsiloxymethyl)-9-hydroxy-9-methoxycarbonyl-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: 42.0%

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

: 215173-31-2
(5R,8R,9S)-8-(tert-butyldiphenylsiloxymethyl)-9-hydroxy-9-methoxycarbonyl-1,7-dioxaspiro[4.4]non-3-ene-2,6-dione

: (4R,5R,8R,9S)-8-(tert-butyldiphenylsiloxymethyl)-9-hydroxy-9-methoxycarbonyl-4-phenylthio-1,7-dioxaspiro[4.4]non-3-ene-2,6-dione

Guidance literature:: With titanium tetrachloride; In dichloromethane; at 0 - 20 ℃; for 1.5h;
DOI:10.1021/jo011157s

Reference yield: 40.0%

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

: 215173-31-2
(5R,8R,9S)-8-(tert-butyldiphenylsiloxymethyl)-9-hydroxy-9-methoxycarbonyl-1,7-dioxaspiro[4.4]non-3-ene-2,6-dione

Guidance literature:: With titanium tetrachloride; In dichloromethane; at 0 - 20 ℃; for 2h;
DOI:10.1021/jo981684k

Reference yield:

: 93499-93-5
dimethyl O-tetrahydro-2H-pyran-2-yl-D-tartrate

: 215173-31-2
(5R,8R,9S)-8-(tert-butyldiphenylsiloxymethyl)-9-hydroxy-9-methoxycarbonyl-1,7-dioxaspiro[4.4]non-3-ene-2,6-dione

Guidance literature:: Multi-step reaction with 6 steps

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

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

2.1: 1.30 g / imidazole / CH₂Cl₂ / 1 h / 0 °C

3.1: 96 percent / dicyclohexylcarbodiimide; 4-(N,N-dimethylamino)pyridine / CH₂Cl₂ / 5 h / 20 °C

4.1: 95 percent / Me₂AlCl / CH₂Cl₂; various solvent(s) / 4 h / -25 - 20 °C

5.1: 98 percent / Dess-Martin periodinane / CH₂Cl₂ / 0.25 h / 20 °C

6.1: 42 percent / TiCl₄ / CH₂Cl₂ / 1.5 h / 0 - 20 °C

With 1H-imidazole; dmap; dimethylsulfide borane complex; dimethylaluminum chloride; titanium tetrachloride; Dess-Martin periodane; dicyclohexyl-carbodiimide; In tetrahydrofuran; dichloromethane; 5.1: Dess-Martin oxidation;
DOI:10.1021/jo011157s