(2R,3S,4S,5R)-2-N-benzylhydroxylamine-1,6-diphenyl-3,4-O-isopropylidene-5-(N-trifluoroacetyl)benzylamine-3,4-hexanediol

Base Information

• Chemical Name: (2R,3S,4S,5R)-2-N-benzylhydroxylamine-1,6-diphenyl-3,4-O-isopropylidene-5-(N-trifluoroacetyl)benzylamine-3,4-hexanediol
• CAS No.: 219586-71-7
• Molecular Formula: C₃₇H₃₉F₃N₂O₄
• Molecular Weight: 632.723
• Mol file: 219586-71-7.mol

Synonyms:

Chemical Property of (2R,3S,4S,5R)-2-N-benzylhydroxylamine-1,6-diphenyl-3,4-O-isopropylidene-5-(N-trifluoroacetyl)benzylamine-3,4-hexanediol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R)-2-N-benzylhydroxylamine-1,6-diphenyl-3,4-O-isopropylidene-5-(N-trifluoroacetyl)benzylamine-3,4-hexanediol

There total 5 articles about (2R,3S,4S,5R)-2-N-benzylhydroxylamine-1,6-diphenyl-3,4-O-isopropylidene-5-(N-trifluoroacetyl)benzylamine-3,4-hexanediol 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: 15.0%

(Z)-N-<(2S,3S,4R)-2,3-O-isopropylidenedioxy-5-phenyl-4-(N-trifluoroacetoxybenzylamino)pentylidene>benzylamine N-oxide (219586-67-1) + benzylmagnesium chloride (6921-34-2) → (2S,3S,4S,5R)-2-N-benzylhydroxylamine-1,6-diphenyl-3,4-O-isopropylidene-5-(N-trifluoroacetyl)benzylamine-3,4-hexanediol (219586-72-8) + (2R,3S,4S,5R)-2-N-benzylhydroxylamine-1,6-diphenyl-3,4-O-isopropylidene-5-(N-trifluoroacetyl)benzylamine-3,4-hexanediol (219586-71-7)

Guidance literature:

In tetrahydrofuran; diethyl ether; at -78 ℃; for 3h;

DOI:10.1021/jo980980u

Reference yield:

(2S,3S)-1-O-benzyl-2,3-O-isopropylidene-5-phenyl-4-(N-trifluoroacetyl)benzylamine-1,2,3-pentantriol → (2R,3S,4S,5R)-2-N-benzylhydroxylamine-1,6-diphenyl-3,4-O-isopropylidene-5-(N-trifluoroacetyl)benzylamine-3,4-hexanediol (219586-71-7)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / Pd(OH)2 / ethyl acetate / 24 h / 760 Torr / Ambient temperature

2: 1.) (COCl)2, DMSO, 2.) DIPEA / 1.) CH₂Cl₂, -78 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C to 0 deg C

3: MgSO₄ / CH₂Cl₂ / 4 h / Ambient temperature

4: 74 percent / tetrahydrofuran; diethyl ether / 3 h / -78 °C

With oxalyl dichloride; hydrogen; magnesium sulfate; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine; palladium dihydroxide; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate;

DOI:10.1021/jo980980u

Reference yield:

N-benzyl hydroxylalmine (622-30-0) → (2R,3S,4S,5R)-2-N-benzylhydroxylamine-1,6-diphenyl-3,4-O-isopropylidene-5-(N-trifluoroacetyl)benzylamine-3,4-hexanediol (219586-71-7)

Guidance literature:

Multi-step reaction with 2 steps

1: MgSO₄ / CH₂Cl₂ / 4 h / Ambient temperature

2: 74 percent / tetrahydrofuran; diethyl ether / 3 h / -78 °C

With magnesium sulfate; In tetrahydrofuran; diethyl ether; dichloromethane;

DOI:10.1021/jo980980u

upstream raw materials:

(Z)-N-<(2S,3S,4R)-2,3-O-isopropylidenedioxy-5-phenyl-4-(N-trifluoroacetoxybenzylamino)pentylidene>benzylamine N-oxide

benzylmagnesium chloride

N-benzyl hydroxylalmine

Downstream raw materials:

(2R,3S,4S,5R)-2,5-diamino-1,6-diphenyl-3,4-hexanediol

(2R,3S,4S,5R)-2,5-bis(phenylmethylamino)-3,4-O-isopropylidene-1,6-diphenyl-3,4-hexanediol

(4R,5S,6S,7R)-hexahydro-5,6-isopropylidenedioxy-4,7-bis(phenylmethyl)-2H-diazapin-2-one

XL₀₇₅