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

Base Information

• Chemical Name: (2R,3S,4S,5S)-2,5-bis(N-benzylhydroxylamine)-3,4-O-isopropylidene-1,6-diphenyl-3,4-hexanediol
• CAS No.: 207561-63-5
• Molecular Formula: C₃₅H₄₀N₂O₄
• Molecular Weight: 552.714
• Mol file: 207561-63-5.mol

Synonyms:(2R,3S,4S,5S)-2,5-bis(N-benzylhydroxylamine)-3,4-O-isopropylidene-1,6-diphenyl-3,4-hexanediol

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (2R,3S,4S,5S)-2,5-bis(N-benzylhydroxylamine)-3,4-O-isopropylidene-1,6-diphenyl-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: 24.0%

(Z,Z)-N,N-<(4S,5S)-2,2-dimethyl-4,5-dimethylethenyl-1,3-dioxolane>-bis(benzylamine N-oxide) (207561-61-3) + benzylmagnesium chloride (6921-34-2) → (2S,3S,4S,5S)-2,5-bis(N-benzylhydroxylamine)-3,4-O-isopropylidene-1,6-diphenyl-3,4-hexanediol (207561-62-4) + (2R,3S,4S,5S)-2,5-bis(N-benzylhydroxylamine)-3,4-O-isopropylidene-1,6-diphenyl-3,4-hexanediol (207561-63-5)

Guidance literature:

In tetrahydrofuran; diethyl ether; at -78 ℃; for 3h; Product distribution; effect of additives; other solvent;

DOI:10.1021/jo980980u

Reference yield:

(2R,3S,4S,5S)-2,5-bis(N-benzylhydroxylamine)-3,4-O-isopropylidene-1,6-diphenyl-3,4-hexanediol (207561-63-5) → (R)-1-[(4S,5S)-5-((S)-1-Amino-2-phenyl-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-phenyl-ethylamine (218271-99-9)

Guidance literature:

With hydrogen; palladium hydroxide - carbon; In ethanol; acetic acid; for 18h; under 2280 Torr;

DOI:10.1016/S0040-4039(98)00330-X

Reference yield:

(2R,3S,4S,5S)-2,5-bis(N-benzylhydroxylamine)-3,4-O-isopropylidene-1,6-diphenyl-3,4-hexanediol (207561-63-5) → (2R,3S,4S,5S)-2,5-diamino-1,6-diphenyl-3,4-hexanediol (207561-64-6)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / Pd(OH)2 / acetic acid; ethanol / 18 h / 2280 Torr / Ambient temperature

2: HCl / H₂O / 3 h / 90 °C

With hydrogenchloride; hydrogen; palladium dihydroxide; In ethanol; water; acetic acid;

DOI:10.1021/jo980980u

upstream raw materials:

(Z,Z)-N,N-<(4S,5S)-2,2-dimethyl-4,5-dimethylethenyl-1,3-dioxolane>-bis(benzylamine N-oxide)

benzylmagnesium chloride

Downstream raw materials:

(R)-1-[(4S,5S)-5-((S)-1-Amino-2-phenyl-ethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-phenyl-ethylamine

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