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

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Chemical Name:(3S,4R,5S)-N-(t-butoxycarbonyl)-2-hydroxy-3,4-bis(methoxymethyl)oxy-5-(t-butyldiphenylsiloxymethyl)pyrrolidine
CAS No.:190902-32-0
Molecular Formula:C₃₀H₄₅NO₈Si
Molecular Weight:575.775
Hs Code.:

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

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

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

There total 13 articles about (3S,4R,5S)-N-(t-butoxycarbonyl)-2-hydroxy-3,4-bis(methoxymethyl)oxy-5-(t-butyldiphenylsiloxymethyl)pyrrolidine 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: 95.0%

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

: 190902-32-0
(3S,4R,5S)-N-(t-butoxycarbonyl)-2-hydroxy-3,4-bis(methoxymethyl)oxy-5-(t-butyldiphenylsiloxymethyl)pyrrolidine

Guidance literature:: With lithium triethylborohydride; In tetrahydrofuran; at -78 ℃;
DOI:10.1016/S0040-4039(97)00636-9

Reference yield:

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

: 190902-32-0
(3S,4R,5S)-N-(t-butoxycarbonyl)-2-hydroxy-3,4-bis(methoxymethyl)oxy-5-(t-butyldiphenylsiloxymethyl)pyrrolidine

Guidance literature:: Multi-step reaction with 9 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

9: 95 percent / LiEt₃BH / tetrahydrofuran / 0.5 h / -78 °C

With 1H-imidazole; dmap; lithium borohydride; N-methyl-2-indolinone; tetrapropylammonium perruthennate; ammonium cerium(IV) nitrate; tetrabutyl ammonium fluoride; lithium triethylborohydride; 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 / 9: Reduction;
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

: 190902-32-0
(3S,4R,5S)-N-(t-butoxycarbonyl)-2-hydroxy-3,4-bis(methoxymethyl)oxy-5-(t-butyldiphenylsiloxymethyl)pyrrolidine

Guidance literature:: Multi-step reaction with 5 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

5: 95 percent / LiEt₃BH / tetrahydrofuran / 0.5 h / -78 °C

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