(2S,3R)-2-{[(R)-4-((4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-3-hydroxy-butyric acid

Base Information

Chemical Name:(2S,3R)-2-{[(R)-4-((4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-3-hydroxy-butyric acid
CAS No.:223923-68-0
Molecular Formula:C₃₆H₅₅N₃O₁₀
Molecular Weight:689.847
Hs Code.:

(2S,3R)-2-{[(R)-4-((4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-3-hydroxy-butyric acid

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Chemical Property of (2S,3R)-2-{[(R)-4-((4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-3-hydroxy-butyric acid

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Technology Process of (2S,3R)-2-{[(R)-4-((4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-3-hydroxy-butyric acid

There total 11 articles about (2S,3R)-2-{[(R)-4-((4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-3-hydroxy-butyric acid 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:

: 134440-96-3
(2S,3R)-N-tert-butoxycarbonyl-2-methyl-3-amino-4-hydroxy methyl butanoate

: 223923-68-0
(2S,3R)-2-{[(R)-4-((4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-3-hydroxy-butyric acid

Guidance literature:: Multi-step reaction with 5 steps

1: 123 mg / oxalyl chloride / CH₂Cl₂ / 1 h / -78 °C

2: 1.) n-BuLi / 1.) THF, -78 deg C (15 min), 0 deg C (30 min), 2.) THF, -> room temp., 20 h

3: 98 percent / aq. LiOH / tetrahydrofuran / 68 h / Ambient temperature

4: 79 percent / 2,4,6-collidine, HATU / dimethylformamide / 14.5 h / Ambient temperature

5: TBAF*H₂O / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) room temp., 5.5 h

With 2,4,6-trimethyl-pyridine; lithium hydroxide; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo982145i

Reference yield:

: 134440-97-4
(2R,3S)-2-(tert-butoxycarbonyl)amino-3-methoxycarbonyl-3-methylbutanal

: 223923-68-0
(2S,3R)-2-{[(R)-4-((4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-3-hydroxy-butyric acid

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) n-BuLi / 1.) THF, -78 deg C (15 min), 0 deg C (30 min), 2.) THF, -> room temp., 20 h

2: 98 percent / aq. LiOH / tetrahydrofuran / 68 h / Ambient temperature

3: 79 percent / 2,4,6-collidine, HATU / dimethylformamide / 14.5 h / Ambient temperature

4: TBAF*H₂O / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) room temp., 5.5 h

With 2,4,6-trimethyl-pyridine; lithium hydroxide; n-butyllithium; tetrabutyl ammonium fluoride; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; N,N-dimethyl-formamide;
DOI:10.1021/jo982145i

Reference yield:

: 82706-51-2
E-(2S,3R)-(N-Boc-amino)-3-methyl-4-hexenoic acid

: 223923-68-0
(2S,3R)-2-{[(R)-4-((4E,6E)-(2S,3S,8S,9S)-3-tert-Butoxycarbonylamino-9-methoxy-2,6,8-trimethyl-10-phenyl-deca-4,6-dienoylamino)-4-methoxycarbonyl-butyryl]-methyl-amino}-3-hydroxy-butyric acid

Guidance literature:: Multi-step reaction with 10 steps

1: 95 percent / NaHCO₃ / dimethylformamide / 24 h / Ambient temperature

2: 90 percent / LiAlH₄ / diethyl ether / 1.5 h / Ambient temperature

3: 96 percent / imidazole / dimethylformamide / 15 h / Ambient temperature

4: 90 percent / O₃, NaOH / 2.25 h / -78 °C

5: 84 percent / NBS / dimethylsulfoxide / 2 h / 10 °C

6: 123 mg / oxalyl chloride / CH₂Cl₂ / 1 h / -78 °C

7: 1.) n-BuLi / 1.) THF, -78 deg C (15 min), 0 deg C (30 min), 2.) THF, -> room temp., 20 h

8: 98 percent / aq. LiOH / tetrahydrofuran / 68 h / Ambient temperature

9: 79 percent / 2,4,6-collidine, HATU / dimethylformamide / 14.5 h / Ambient temperature

10: TBAF*H₂O / tetrahydrofuran / 1.) 0 deg C, 2 h, 2.) room temp., 5.5 h

With 1H-imidazole; 2,4,6-trimethyl-pyridine; lithium hydroxide; sodium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; ozone; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In tetrahydrofuran; diethyl ether; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/jo982145i