(2S,4R,5S)-2,4-dibenzyloxy-6-hydroxy-5,6-N,O-isopropylidene-5-(tert-butoxycarbonylamino)hexanal

Base Information

Chemical Name:(2S,4R,5S)-2,4-dibenzyloxy-6-hydroxy-5,6-N,O-isopropylidene-5-(tert-butoxycarbonylamino)hexanal
CAS No.:149356-12-7
Molecular Formula:C₂₈H₃₇NO₆
Molecular Weight:483.605
Hs Code.:

Synonyms:(2S,4R,5S)-2,4-dibenzyloxy-6-hydroxy-5,6-N,O-isopropylidene-5-(tert-butoxycarbonylamino)hexanal

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Chemical Property of (2S,4R,5S)-2,4-dibenzyloxy-6-hydroxy-5,6-N,O-isopropylidene-5-(tert-butoxycarbonylamino)hexanal

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Technology Process of (2S,4R,5S)-2,4-dibenzyloxy-6-hydroxy-5,6-N,O-isopropylidene-5-(tert-butoxycarbonylamino)hexanal

There total 6 articles about (2S,4R,5S)-2,4-dibenzyloxy-6-hydroxy-5,6-N,O-isopropylidene-5-(tert-butoxycarbonylamino)hexanal 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:

: (S)-4-[(1R,3S)-1,3-Bis-benzyloxy-3-(3-methyl-2,3-dihydro-thiazol-2-yl)-propyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

: 149356-12-7
(2S,4R,5S)-2,4-dibenzyloxy-6-hydroxy-5,6-N,O-isopropylidene-5-(tert-butoxycarbonylamino)hexanal

Guidance literature:: With water; mercury dichloride; In acetonitrile; for 15h; Yield given; Ambient temperature;
DOI:10.1016/S0040-4020(01)80389-6

Reference yield:

: 100-39-0
benzyl bromide

: 149356-12-7
(2S,4R,5S)-2,4-dibenzyloxy-6-hydroxy-5,6-N,O-isopropylidene-5-(tert-butoxycarbonylamino)hexanal

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) NaH / 1.) DMF, 0 deg C, 15 min, 2.) r. t., 12 h

2: acetonitrile / 16 h / Heating

3: NaBH₄ / methanol / 0.5 h / Heating

4: HgCl₂, H₂O / acetonitrile / 15 h / Ambient temperature

With sodium tetrahydroborate; water; sodium hydride; mercury dichloride; In methanol; acetonitrile;
DOI:10.1016/S0040-4020(01)80389-6

Reference yield:

: 128459-42-7
(3R,4S)-N-(tert-Butoxycarbonyl)-4,5-N,O-isopropyliden-4-amino-3,5-dihydroxy-1-(2-thiazolyl)-1-pentanone

: 149356-12-7
(2S,4R,5S)-2,4-dibenzyloxy-6-hydroxy-5,6-N,O-isopropylidene-5-(tert-butoxycarbonylamino)hexanal

Guidance literature:: Multi-step reaction with 5 steps

1: 92 percent / Et₂BOMe, NaBH₄ / tetrahydrofuran; methanol / 6 h / -78 °C

2: 1.) NaH / 1.) DMF, 0 deg C, 15 min, 2.) r. t., 12 h

3: acetonitrile / 16 h / Heating

4: NaBH₄ / methanol / 0.5 h / Heating

5: HgCl₂, H₂O / acetonitrile / 15 h / Ambient temperature

With sodium tetrahydroborate; diethyl methoxy borane; water; sodium hydride; mercury dichloride; In tetrahydrofuran; methanol; acetonitrile;
DOI:10.1016/S0040-4020(01)80389-6