((1R,3S,4S)-4-tert-Butoxycarbonylamino-3-hydroxy-5-phenoxy-1-phenoxymethyl-pentyl)-carbamic acid tert-butyl ester

Base Information

Chemical Name:((1R,3S,4S)-4-tert-Butoxycarbonylamino-3-hydroxy-5-phenoxy-1-phenoxymethyl-pentyl)-carbamic acid tert-butyl ester
CAS No.:211994-16-0
Molecular Formula:C₂₈H₄₀N₂O₇
Molecular Weight:516.635
Hs Code.:

Synonyms:((1R,3S,4S)-4-tert-Butoxycarbonylamino-3-hydroxy-5-phenoxy-1-phenoxymethyl-pentyl)-carbamic acid tert-butyl ester

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Chemical Property of ((1R,3S,4S)-4-tert-Butoxycarbonylamino-3-hydroxy-5-phenoxy-1-phenoxymethyl-pentyl)-carbamic acid tert-butyl ester

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Technology Process of ((1R,3S,4S)-4-tert-Butoxycarbonylamino-3-hydroxy-5-phenoxy-1-phenoxymethyl-pentyl)-carbamic acid tert-butyl ester

There total 12 articles about ((1R,3S,4S)-4-tert-Butoxycarbonylamino-3-hydroxy-5-phenoxy-1-phenoxymethyl-pentyl)-carbamic acid tert-butyl ester 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: 59.0%

: 211994-14-8
{(S)-1-[(4R,5R)-5-((S)-1-tert-Butoxycarbonylamino-2-phenoxy-ethyl)-2-thioxo-[1,3]dioxolan-4-yl]-2-phenoxy-ethyl}-carbamic acid tert-butyl ester

: 1054653-06-3
[(R)-2-((4S,5S)-2-Oxo-4-phenoxymethyl-oxazolidin-5-yl)-1-phenoxymethyl-ethyl]-carbamic acid tert-butyl ester

: {(S)-1-[(4R,5R)-5-((S)-1-tert-Butoxycarbonylamino-2-phenoxy-ethyl)-[1,3]dioxolan-4-yl]-2-phenoxy-ethyl}-carbamic acid tert-butyl ester

: {(S)-1-[(4R,5R)-5-((S)-1-tert-Butoxycarbonylamino-2-phenoxy-ethyl)-2-oxo-[1,3]oxathiolan-4-yl]-2-phenoxy-ethyl}-carbamic acid tert-butyl ester

: 211994-16-0
((1R,3S,4S)-4-tert-Butoxycarbonylamino-3-hydroxy-5-phenoxy-1-phenoxymethyl-pentyl)-carbamic acid tert-butyl ester

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 1.16667h; Heating;
DOI:10.1021/jo971562c

Reference yield: 56.0%

: 24424-99-5
di-tert-butyl dicarbonate

: 1054653-06-3
[(R)-2-((4S,5S)-2-Oxo-4-phenoxymethyl-oxazolidin-5-yl)-1-phenoxymethyl-ethyl]-carbamic acid tert-butyl ester

: 211994-16-0
((1R,3S,4S)-4-tert-Butoxycarbonylamino-3-hydroxy-5-phenoxy-1-phenoxymethyl-pentyl)-carbamic acid tert-butyl ester

Guidance literature:: With barium dihydroxide;
DOI:10.1021/jo971562c

Reference yield:

: 211993-82-7
2,5-diazido-2,5-dideoxy-3,4-O-isopropylidene-1,6-di-O-phenyl-L-iditol

: 211994-16-0
((1R,3S,4S)-4-tert-Butoxycarbonylamino-3-hydroxy-5-phenoxy-1-phenoxymethyl-pentyl)-carbamic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 96 percent / acetyl chloride / methanol / 24 h / Ambient temperature

2: H₂ / Pd/C / ethyl acetate / 16 h

3: 28 percent / Et₃N / CH₂Cl₂ / Ambient temperature

4: 0.050 g / CrO₃, Ac₂O, pyridine / CH₂Cl₂ / 3 h

5: 1.) NaBH₄, 2.) Ba(OH)2*8H₂O / 1.) MeOH, 1 h, 2.) H₂O, 80 deg C, 24 h

6: ethyl acetate / 4 h

7: 70 percent / tetrahydrofuran / 22 h / 55 °C

8: Bu₃SnH, 2,2'-azobis(isobutyronitrile) / toluene / 0.83 h / Heating

9: 56 percent / 1.) Ba(OH)2

With pyridine; chromium(VI) oxide; barium dihydroxide; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); hydrogen; tri-n-butyl-tin hydride; acetic anhydride; triethylamine; acetyl chloride; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; toluene;
DOI:10.1021/jo971562c