(4S,5R,9S)-8-(Z)-benzylidene-4-ethyl-2,2-dimethyl-9-triisopropylsiloxy-1,3-dioxa-7-azaspiro[4.4]nonan-6-one

Base Information

Chemical Name:(4S,5R,9S)-8-(Z)-benzylidene-4-ethyl-2,2-dimethyl-9-triisopropylsiloxy-1,3-dioxa-7-azaspiro[4.4]nonan-6-one
CAS No.:474915-81-6
Molecular Formula:C₂₆H₄₁NO₄Si
Molecular Weight:459.701
Hs Code.:

Synonyms:(4S,5R,9S)-8-(Z)-benzylidene-4-ethyl-2,2-dimethyl-9-triisopropylsiloxy-1,3-dioxa-7-azaspiro[4.4]nonan-6-one

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Chemical Property of (4S,5R,9S)-8-(Z)-benzylidene-4-ethyl-2,2-dimethyl-9-triisopropylsiloxy-1,3-dioxa-7-azaspiro[4.4]nonan-6-one

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Technology Process of (4S,5R,9S)-8-(Z)-benzylidene-4-ethyl-2,2-dimethyl-9-triisopropylsiloxy-1,3-dioxa-7-azaspiro[4.4]nonan-6-one

There total 7 articles about (4S,5R,9S)-8-(Z)-benzylidene-4-ethyl-2,2-dimethyl-9-triisopropylsiloxy-1,3-dioxa-7-azaspiro[4.4]nonan-6-one 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: 92.0%

: 474915-79-2
(2R,3S)-2,3-O-isopropylidene-2-[(S)-1-triisopropylsiloxy-3-phenyl-2-propynyl]pentanamide

: (4S,5R,9S)-8-(E)-benzylidene-4-ethyl-2,2-dimethyl-9-triisopropylsiloxy-1,3-dioxa-7-azaspiro[4.4]nonan-6-one

: 474915-81-6
(4S,5R,9S)-8-(Z)-benzylidene-4-ethyl-2,2-dimethyl-9-triisopropylsiloxy-1,3-dioxa-7-azaspiro[4.4]nonan-6-one

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 1h;
DOI:10.1021/ja0276826

Reference yield:

: (4R,5S)-5-Ethyl-2,2-dimethyl-4-(3-phenyl-propynoyl)-[1,3]dioxolane-4-carboxylic acid methyl ester

: 474915-81-6
(4S,5R,9S)-8-(Z)-benzylidene-4-ethyl-2,2-dimethyl-9-triisopropylsiloxy-1,3-dioxa-7-azaspiro[4.4]nonan-6-one

Guidance literature:: Multi-step reaction with 6 steps

1: NaBH₄; CeCl₃ / ethanol

2: 98 percent / 2,6-lutidine / CH₂Cl₂ / 13 h / 20 °C

3: LiOH / 2-methyl-propan-2-ol / 48 h / 110 °C

4: oxalyl chloride; Et₃N; DMF / CH₂Cl₂ / 4 h / 20 °C

5: 273 mg / liq. NH₃ / 1 h / 20 °C

6: 92 percent / NaH / dimethylformamide / 1 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; sodium tetrahydroborate; cerium(III) chloride; oxalyl dichloride; ammonia; sodium hydride; triethylamine; N,N-dimethyl-formamide; In ethanol; dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ja0276826

Reference yield:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 474915-81-6
(4S,5R,9S)-8-(Z)-benzylidene-4-ethyl-2,2-dimethyl-9-triisopropylsiloxy-1,3-dioxa-7-azaspiro[4.4]nonan-6-one

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 13 h / 20 °C

2: LiOH / 2-methyl-propan-2-ol / 48 h / 110 °C

3: oxalyl chloride; Et₃N; DMF / CH₂Cl₂ / 4 h / 20 °C

4: 273 mg / liq. NH₃ / 1 h / 20 °C

5: 92 percent / NaH / dimethylformamide / 1 h / 20 °C

With 2,6-dimethylpyridine; lithium hydroxide; oxalyl dichloride; ammonia; sodium hydride; triethylamine; N,N-dimethyl-formamide; In dichloromethane; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/ja0276826