(2S,3S)-4-(3,4-bis-(difluoromethoxy)phenyl)-3-(tert-butoxycarbonylamino)-2-hydroxybutyl acetate

Base Information

• Chemical Name: (2S,3S)-4-(3,4-bis-(difluoromethoxy)phenyl)-3-(tert-butoxycarbonylamino)-2-hydroxybutyl acetate
• CAS No.: 1373754-48-3
• Molecular Formula: C₁₉H₂₅F₄NO₇
• Molecular Weight: 455.404

Synonyms:(2S,3S)-4-(3,4-bis-(difluoromethoxy)phenyl)-3-(tert-butoxycarbonylamino)-2-hydroxybutyl acetate

Chemical Property of (2S,3S)-4-(3,4-bis-(difluoromethoxy)phenyl)-3-(tert-butoxycarbonylamino)-2-hydroxybutyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-4-(3,4-bis-(difluoromethoxy)phenyl)-3-(tert-butoxycarbonylamino)-2-hydroxybutyl acetate

There total 6 articles about (2S,3S)-4-(3,4-bis-(difluoromethoxy)phenyl)-3-(tert-butoxycarbonylamino)-2-hydroxybutyl acetate 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-(3,4-bis(difluoromethoxy)phenyl)-3-(tert-butoxycarbonylamino)-2-oxobutyl acetate (1373754-45-0) → (2S,3S)-4-(3,4-bis-(difluoromethoxy)phenyl)-3-(tert-butoxycarbonylamino)-2-hydroxybutyl acetate (1373754-48-3)

Guidance literature:

With lithium tri-t-butoxyaluminum hydride; In tetrahydrofuran; methanol; ethanol; at -78 - 20 ℃; for 1.25h;

DOI:10.1021/jm300119p

Reference yield:

trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate (121056-95-9,89524-98-1) → (2S,3S)-4-(3,4-bis-(difluoromethoxy)phenyl)-3-(tert-butoxycarbonylamino)-2-hydroxybutyl acetate (1373754-48-3)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 2.33 h / 0 - 20 °C

2.1: hydrogen; (1R,2S)-2-tert-butyl-1-((1R,2S)-2-tertbutyl-2,3-dihydro-1H-isophosphindol-1-yl)-2,3-dihydro-1H-isophosphindole / methanol / 2 h / 2585.81 Torr / Sealed tube

3.1: lithium hydroxide / tetrahydrofuran / 1.5 h / 0 °C

4.1: triethylamine; isobutyl chloroformate / tetrahydrofuran / 2 h / 0 °C

4.2: 2 h

5.1: hydrogen bromide / tetrahydrofuran / 0.17 h / 0 °C

5.2: 0.5 h / 20 °C

6.1: lithium tri-t-butoxyaluminum hydride / methanol; tetrahydrofuran; ethanol / 1.25 h / -78 - 20 °C

With (1R,2S)-2-tert-butyl-1-((1R,2S)-2-tertbutyl-2,3-dihydro-1H-isophosphindol-1-yl)-2,3-dihydro-1H-isophosphindole; isobutyl chloroformate; hydrogen bromide; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium tri-t-butoxyaluminum hydride; triethylamine; lithium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane;

DOI:10.1021/jm300119p

Reference yield:

(Z)-methyl 3-(3,4-bis(difluoromethoxy)phenyl)-2-(tert-butoxycarbonylamino)acrylate (1373754-40-5) → (2S,3S)-4-(3,4-bis-(difluoromethoxy)phenyl)-3-(tert-butoxycarbonylamino)-2-hydroxybutyl acetate (1373754-48-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: hydrogen; (1R,2S)-2-tert-butyl-1-((1R,2S)-2-tertbutyl-2,3-dihydro-1H-isophosphindol-1-yl)-2,3-dihydro-1H-isophosphindole / methanol / 2 h / 2585.81 Torr / Sealed tube

2.1: lithium hydroxide / tetrahydrofuran / 1.5 h / 0 °C

3.1: triethylamine; isobutyl chloroformate / tetrahydrofuran / 2 h / 0 °C

3.2: 2 h

4.1: hydrogen bromide / tetrahydrofuran / 0.17 h / 0 °C

4.2: 0.5 h / 20 °C

5.1: lithium tri-t-butoxyaluminum hydride / methanol; tetrahydrofuran; ethanol / 1.25 h / -78 - 20 °C

With (1R,2S)-2-tert-butyl-1-((1R,2S)-2-tertbutyl-2,3-dihydro-1H-isophosphindol-1-yl)-2,3-dihydro-1H-isophosphindole; isobutyl chloroformate; hydrogen bromide; hydrogen; lithium tri-t-butoxyaluminum hydride; triethylamine; lithium hydroxide; In tetrahydrofuran; methanol; ethanol;

DOI:10.1021/jm300119p

upstream raw materials:

(S)-4-(3,4-bis(difluoromethoxy)phenyl)-3-(tert-butoxycarbonylamino)-2-oxobutyl acetate

trimethyl 2-(tert-butoxycarbonylamino)phosphonoacetate

(Z)-methyl 3-(3,4-bis(difluoromethoxy)phenyl)-2-(tert-butoxycarbonylamino)acrylate

(S)-methyl 3-(3,4-bis(difluoromethoxy)phenyl)-2-(tert-butoxycarbonylamino)propanoate

Downstream raw materials:

(4S)-tert-butyl 4-(3,4-bis(difluoromethoxy)benzyl)-5-formyl-2,2-dimethyloxazolidine-3-carboxylate

(4S,5R)-tertbutyl 4-(3,4-bis(difluoromethoxy)benzyl)-2,2-dimethyl-5-(((S)-6′-neopentyl-3′,4′-dihydrospiro[cyclobutane-1,2′-pyrano[2,3-b]-pyridine]-4′-ylamino)methyl)oxazolidine-3-carboxylate

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