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

Base Information

• Chemical Name: (2S,3S,4S,5R)-2-N-benzylhydroxylamine-5-tert-butoxycarbonylamine-1,6-diphenyl-3,4-O-isopropylidene-3,4-hexanediol
• CAS No.: 219586-74-0
• Molecular Formula: C₃₃H₄₂N₂O₅
• Molecular Weight: 546.707
• Mol file: 219586-74-0.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 3 articles about (2S,3S,4S,5R)-2-N-benzylhydroxylamine-5-tert-butoxycarbonylamine-1,6-diphenyl-3,4-O-isopropylidene-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: 23.0%

(Z)-N-<(2S,3S,4R)-4-N-tert-butoxycarbonylamine-2,3-O-isopropylidenedioxy-5-phenylpentylidene>benzylamine N-oxide (219586-69-3) + benzylmagnesium chloride (6921-34-2) → (2S,3S,4S,5R)-2-N-benzylhydroxylamine-5-tert-butoxycarbonylamine-1,6-diphenyl-3,4-O-isopropylidene-3,4-hexanediol (219586-74-0) + (2R,3S,4S,5R)-2-N-benzylhydroxylamine-5-tert-butoxycarbonylamine-1,6-diphenyl-3,4-O-isopropylidene-3,4-hexanediol (219586-73-9)

Guidance literature:

In tetrahydrofuran; diethyl ether; at -78 ℃; for 5h;

DOI:10.1021/jo980980u

Reference yield:

[(R)-1-((4S,5R)-5-Formyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-phenyl-ethyl]-carbamic acid tert-butyl ester → (2S,3S,4S,5R)-2-N-benzylhydroxylamine-5-tert-butoxycarbonylamine-1,6-diphenyl-3,4-O-isopropylidene-3,4-hexanediol (219586-74-0)

Guidance literature:

Multi-step reaction with 2 steps

1: MgSO₄ / CH₂Cl₂ / 4 h / Ambient temperature

2: 23 percent / tetrahydrofuran; diethyl ether / 5 h / -78 °C

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

DOI:10.1021/jo980980u

Reference yield:

(2S,3S)-4-tert-butoxycarbonylamino-2,3-O-isopropylidene-5-phenyl-1,2,3-pentantriol → (2S,3S,4S,5R)-2-N-benzylhydroxylamine-5-tert-butoxycarbonylamine-1,6-diphenyl-3,4-O-isopropylidene-3,4-hexanediol (219586-74-0)

Guidance literature:

Multi-step reaction with 3 steps

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

2: MgSO₄ / CH₂Cl₂ / 4 h / Ambient temperature

3: 23 percent / tetrahydrofuran; diethyl ether / 5 h / -78 °C

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

DOI:10.1021/jo980980u

upstream raw materials:

(Z)-N-<(2S,3S,4R)-4-N-tert-butoxycarbonylamine-2,3-O-isopropylidenedioxy-5-phenylpentylidene>benzylamine N-oxide

benzylmagnesium chloride

Downstream raw materials:

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

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