methyl (3S,4R)-3-(N-benzylhydroxyamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-N,O-isopropylidenepentanoate

Base Information

• Chemical Name: methyl (3S,4R)-3-(N-benzylhydroxyamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-N,O-isopropylidenepentanoate
• CAS No.: 213752-98-8
• Molecular Formula: C₂₁H₃₂N₂O₆
• Molecular Weight: 408.495

Synonyms:methyl (3S,4R)-3-(N-benzylhydroxyamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-N,O-isopropylidenepentanoate

Chemical Property of methyl (3S,4R)-3-(N-benzylhydroxyamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-N,O-isopropylidenepentanoate

Chemical Property:

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Technology Process of methyl (3S,4R)-3-(N-benzylhydroxyamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-N,O-isopropylidenepentanoate

There total 4 articles about methyl (3S,4R)-3-(N-benzylhydroxyamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-N,O-isopropylidenepentanoate 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: 100.0%

methyl (3S,4R)-3-(N-benzyl-tert-butyldimethylsiloxyamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-N,O-isopropylidenepentanoate (213752-96-6) → methyl (3S,4R)-3-(N-benzylhydroxyamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-N,O-isopropylidenepentanoate (213752-98-8)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1016/S0040-4039(98)01323-9

Reference yield: 81.0%

N-benzylhydroxylamine hydrochloride (29601-98-7) + N-(tert-butoxycarbonyl)-2,2-dimethyl-4(R)-<2'-carboxymethylethenyl>-oxazolidine (123751-10-0) → methyl (3S,4R)-3-(N-benzylhydroxyamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-N,O-isopropylidenepentanoate (213752-98-8) + methyl (3R,4R)-3-(N-benzylhydroxyamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-N,O-isopropylidenepentanoate (298198-07-9)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1021/jo0002689

Reference yield: 37.0%

N-benzylhydroxylamine hydrochloride (29601-98-7) + tert-butyl (4R)-4-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate (123751-09-7) → methyl (3S,4R)-3-(N-benzylhydroxyamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-N,O-isopropylidenepentanoate (213752-98-8) + methyl (3R,4R)-3-(N-benzylhydroxyamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-N,O-isopropylidenepentanoate (298198-07-9)

Guidance literature:

In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1021/jo0002689

upstream raw materials:

methyl (3S,4R)-3-(N-benzyl-tert-butyldimethylsiloxyamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-N,O-isopropylidenepentanoate

N-benzylhydroxylamine hydrochloride

N-(tert-butoxycarbonyl)-2,2-dimethyl-4(R)-<2'-carboxymethylethenyl>-oxazolidine

tert-butyl (4R)-4-[(1E)-3-methoxy-3-oxoprop-1-en-1-yl]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate

Downstream raw materials:

(R)-4-((S)-1-Benzylamino-2-methoxycarbonyl-ethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

{(R)-1-[(3S,5R)-2-Benzyl-5-(5-methyl-2,4-dioxo-3,4-dihydro-2H-pyrimidin-1-yl)-isoxazolidin-3-yl]-2-oxo-ethyl}-carbamic acid tert-butyl ester

1-{(3S,5S)-2-benzyl-3-[(4R)-3-(tert-butoxycarbonylamino)-2-hydroxyethyl]isoxazolidin-5-yl}thymine

1-{(3S,5S)-2-benzyl-3-[(4R)-3-(tert-butoxycarbonylamino)-2,2-dimethyl-1,3-oxazolidin-4-yl]isoxazolidin-5-yl}uracil

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