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

Base Information

Chemical Name:methyl (3S,4R)-3-(N-benzyl-tert-butyldimethylsiloxyamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-N,O-isopropylidenepentanoate
CAS No.:213752-96-6
Molecular Formula:C₂₇H₄₆N₂O₆Si
Molecular Weight:522.758
Hs Code.:

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

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

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

There total 1 articles about methyl (3S,4R)-3-(N-benzyl-tert-butyldimethylsiloxyamino)-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: 79.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 77086-38-5
ketene t-butyldimethylsilyl methyl acetal

: 158723-45-6,188965-45-9
(Z)-N-[(4R)-3-(tert-butoxycarbonyl)-2,2-dimethyl-1,3-oxazolidin-4-yl]benzylamine N-oxide

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

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

Guidance literature:: In dichloromethane; at -80 - -70 ℃; for 2h;
DOI:10.1021/jo0002689

Reference yield: 100.0%

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

: 213752-98-8
methyl (3S,4R)-3-(N-benzylhydroxyamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-N,O-isopropylidenepentanoate

Guidance literature:: With pyridine hydrogenfluoride; In tetrahydrofuran; at 0 ℃; for 1h;
DOI:10.1016/S0040-4039(98)01323-9

Reference yield:

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

: 213752-99-9
methyl (3S,4R)-3-benzamido-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-N,O-isopropylidenepentanoate

Guidance literature:: Multi-step reaction with 4 steps

1: 88 percent / HF-pyridine complex / tetrahydrofuran / 1 h / 0 °C

2: Zn; Cu(OAc)2 / acetic acid; H₂O / 1 h / 70 °C

3: H₂ / Pd/C / methanol / 4 h / 2585.81 Torr

4: 0.463 g / pyridine / CH₂Cl₂ / 16 h

With pyridine; copper diacetate; hydrogen; pyridine hydrogenfluoride; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; acetic acid; 1: Substitution / 2: Reduction / 3: Hydrogenolysis / 4: Acylation;
DOI:10.1021/jo0002689