(3S,4R,5S)-N-(t-butoxycarbonyl)-3,4-bis(methoxymethyl)oxy-5-(t-butyldiphenylsiloxymethyl)-2-pyrrolidinone

Base Information

Chemical Name:(3S,4R,5S)-N-(t-butoxycarbonyl)-3,4-bis(methoxymethyl)oxy-5-(t-butyldiphenylsiloxymethyl)-2-pyrrolidinone
CAS No.:190902-31-9
Molecular Formula:C₃₀H₄₃NO₈Si
Molecular Weight:573.759
Hs Code.:

Synonyms:(3S,4R,5S)-N-(t-butoxycarbonyl)-3,4-bis(methoxymethyl)oxy-5-(t-butyldiphenylsiloxymethyl)-2-pyrrolidinone

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Chemical Property of (3S,4R,5S)-N-(t-butoxycarbonyl)-3,4-bis(methoxymethyl)oxy-5-(t-butyldiphenylsiloxymethyl)-2-pyrrolidinone

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Technology Process of (3S,4R,5S)-N-(t-butoxycarbonyl)-3,4-bis(methoxymethyl)oxy-5-(t-butyldiphenylsiloxymethyl)-2-pyrrolidinone

There total 11 articles about (3S,4R,5S)-N-(t-butoxycarbonyl)-3,4-bis(methoxymethyl)oxy-5-(t-butyldiphenylsiloxymethyl)-2-pyrrolidinone 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:

: 166542-99-0
(2S,3R)-2,3-bis(methoxymethoxy)-4-<(t-butyldimethylsilyl)oxy>butanal

: 190902-31-9
(3S,4R,5S)-N-(t-butoxycarbonyl)-3,4-bis(methoxymethyl)oxy-5-(t-butyldiphenylsiloxymethyl)-2-pyrrolidinone

Guidance literature:: Multi-step reaction with 8 steps

1: 96 percent / tetrahydrofuran / 1 h / 20 °C

2: 87 percent / TBAF / tetrahydrofuran / 2 h / 20 °C

3: NMO; TPAP / CH₂Cl₂ / 1 h / Heating

4: methanol / 0.5 h

5: 41 percent / LiBH₄ / tetrahydrofuran / 20 h / 20 °C

6: 92 percent / imidazole / dimethylformamide / 6 h

7: 82 percent / CAN / acetonitrile; H₂O / 0 - 20 °C

8: Et₃N; DMAP / CH₂Cl₂

With 1H-imidazole; dmap; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; ammonium cerium(IV) nitrate; tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: Condensation / 2: Substitution / 3: Cyclization / 4: Hydrolysis / 5: Reduction / 6: Substitution / 7: Substitution / 8: Acylation;
DOI:10.1016/S0040-4020(99)00459-7

Reference yield:

: 190902-21-7
(3S,4R,5RS)-N-(4-methoxybenzyl)-3,4-bis(methoxymethyl)oxy-5-cyano-2-pyrrolidinone

: 190902-31-9
(3S,4R,5S)-N-(t-butoxycarbonyl)-3,4-bis(methoxymethyl)oxy-5-(t-butyldiphenylsiloxymethyl)-2-pyrrolidinone

Guidance literature:: Multi-step reaction with 5 steps

1: methanol / 0.5 h

2: 41 percent / LiBH₄ / tetrahydrofuran / 20 h / 20 °C

3: 92 percent / imidazole / dimethylformamide / 6 h

4: 82 percent / CAN / acetonitrile; H₂O / 0 - 20 °C

5: Et₃N; DMAP / CH₂Cl₂

With 1H-imidazole; dmap; lithium borohydride; ammonium cerium(IV) nitrate; triethylamine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: Hydrolysis / 2: Reduction / 3: Substitution / 4: Substitution / 5: Acylation;
DOI:10.1016/S0040-4020(99)00459-7

Reference yield:

: 190902-22-8
(3S,4R,5RS)-N-(4-methoxybenzyl)-3,4-bis(methoxymethyl)oxy-5-methoxycarbonyl-2-pyrrolidinone

: 190902-31-9
(3S,4R,5S)-N-(t-butoxycarbonyl)-3,4-bis(methoxymethyl)oxy-5-(t-butyldiphenylsiloxymethyl)-2-pyrrolidinone

Guidance literature:: Multi-step reaction with 4 steps

1: 41 percent / LiBH₄ / tetrahydrofuran / 20 h / 20 °C

2: 92 percent / imidazole / dimethylformamide / 6 h

3: 82 percent / CAN / acetonitrile; H₂O / 0 - 20 °C

4: Et₃N; DMAP / CH₂Cl₂

With 1H-imidazole; dmap; lithium borohydride; ammonium cerium(IV) nitrate; triethylamine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 1: Reduction / 2: Substitution / 3: Substitution / 4: Acylation;
DOI:10.1016/S0040-4020(99)00459-7