(3S,4S)-benzyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-methyl-5-oxopentanoate

Base Information

Chemical Name:(3S,4S)-benzyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-methyl-5-oxopentanoate
CAS No.:1443753-93-2
Molecular Formula:C₂₁H₃₁NO₅
Molecular Weight:377.481
Hs Code.:

Synonyms:(3S,4S)-benzyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-methyl-5-oxopentanoate

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Chemical Property of (3S,4S)-benzyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-methyl-5-oxopentanoate

Chemical Property:

Purity/Quality:

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Technology Process of (3S,4S)-benzyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-methyl-5-oxopentanoate

There total 8 articles about (3S,4S)-benzyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-methyl-5-oxopentanoate 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:

: C₁₄H₂₅NO₅

: 100-39-0
benzyl bromide

: 1443753-93-2
(3S,4S)-benzyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-methyl-5-oxopentanoate

Guidance literature:: With sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 20 ℃; for 24h; Inert atmosphere;
DOI:10.1016/j.bmc.2012.05.036

Reference yield:

: 1210057-70-7
(S) ethyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-methyl-5-oxo-2-pentenoate

: 1443753-93-2
(3S,4S)-benzyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-methyl-5-oxopentanoate

Guidance literature:: Multi-step reaction with 3 steps

1: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 12 h / 20 °C

2: water; lithium hydroxide monohydrate / tetrahydrofuran / 12 h / 0 - 20 °C

3: sodium hydrogencarbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

With lithium hydroxide monohydrate; palladium 10% on activated carbon; water; hydrogen; sodium hydrogencarbonate; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1016/j.bmc.2012.05.036

Reference yield:

: 95715-85-8
2-(tert-butoxycarbonylamino)-3-hydroxypropionic acid methyl ester

: 1443753-93-2
(3S,4S)-benzyl N,O-isopropylidenyl-4-(N-tert-butyloxycarbonylamino)-3-methyl-5-oxopentanoate

Guidance literature:: Multi-step reaction with 8 steps

1: boron trifluoride diethyl etherate / acetone / 2 h / 20 °C

2: water; lithium hydroxide monohydrate / methanol / 4 h / 20 °C

3: (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine / 3 h / 20 °C

4: tetrahydrofuran / 1 h / -78 °C

5: sodium hydride / 24 h / 0 °C

6: palladium 10% on activated carbon; hydrogen / methanol; ethyl acetate / 12 h / 20 °C

7: water; lithium hydroxide monohydrate / tetrahydrofuran / 12 h / 0 - 20 °C

8: sodium hydrogencarbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere

With lithium hydroxide monohydrate; palladium 10% on activated carbon; boron trifluoride diethyl etherate; water; hydrogen; sodium hydride; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; In tetrahydrofuran; methanol; ethyl acetate; N,N-dimethyl-formamide; acetone;
DOI:10.1016/j.bmc.2012.05.036