(3S,4R,5R)-3-(N-benzylhydroxylamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-O-isopropylidene-1-hexene

Base Information

Chemical Name:(3S,4R,5R)-3-(N-benzylhydroxylamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-O-isopropylidene-1-hexene
CAS No.:299409-54-4
Molecular Formula:C₂₁H₃₂N₂O₄
Molecular Weight:376.496
Hs Code.:

Synonyms:(3S,4R,5R)-3-(N-benzylhydroxylamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-O-isopropylidene-1-hexene

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Chemical Property of (3S,4R,5R)-3-(N-benzylhydroxylamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-O-isopropylidene-1-hexene

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Technology Process of (3S,4R,5R)-3-(N-benzylhydroxylamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-O-isopropylidene-1-hexene

There total 4 articles about (3S,4R,5R)-3-(N-benzylhydroxylamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-O-isopropylidene-1-hexene 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: 87.0%

: 1826-67-1
vinyl magnesium bromide

: 299409-53-3
(Z)-N-{[(4S,5R)-3-(tert-butoxycarbonyl)-2,2,5-trimethyl-1,3-oxazolidin-4-yl]methylidene}benzylamine N-oxide

: 299409-54-4
(3S,4R,5R)-3-(N-benzylhydroxylamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-O-isopropylidene-1-hexene

: (3R,4R,5R)-3-(N-benzylhydroxylamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-O-isopropylidene-1-hexene

Guidance literature:: In tetrahydrofuran; at -30 ℃; for 2h;
DOI:10.1080/00397910008087449

Reference yield:

: 77-76-9
2,2-dimethoxy-propane

: [(1R,2S)-2-(Benzyl-hydroxy-amino)-1-((R)-1-hydroxy-ethyl)-but-3-enyl]-carbamic acid tert-butyl ester

: 299409-54-4
(3S,4R,5R)-3-(N-benzylhydroxylamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-O-isopropylidene-1-hexene

Guidance literature:: With boron trifluoride diethyl etherate; In acetone; at 20 ℃; for 2h;
DOI:10.1080/00397910008087449

Reference yield:

: (Z)-N-<(2R,3R)-2-(tert-butoxycarbonylamino)-3-(tert-butyldiphenylsiloxy)butylidene>benzylamine N-oxide

: 299409-54-4
(3S,4R,5R)-3-(N-benzylhydroxylamino)-4-(tert-butoxycarbonylamino)-5-hydroxy-4,5-O-isopropylidene-1-hexene

Guidance literature:: Multi-step reaction with 3 steps

1: 79 percent / tetrahydrofuran / 2 h / -30 °C

2: Bu₄NF / tetrahydrofuran / 1 h / 20 °C

3: 28 mg / BF₃*Et₂O / acetone / 2 h / 20 °C

With boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; In tetrahydrofuran; acetone; 1: Addition / 2: desilylation / 3: cyclocondensation;
DOI:10.1080/00397910008087449