Benzoic acid (3aR,4R,6R,6aS)-6-benzyloxyamino-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester

Base Information

• Chemical Name: Benzoic acid (3aR,4R,6R,6aS)-6-benzyloxyamino-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester
• CAS No.: 138946-58-4
• Molecular Formula: C₂₂H₂₅NO₅
• Molecular Weight: 383.444
• Mol file: 138946-58-4.mol

Synonyms:Benzoic acid (3aR,4R,6R,6aS)-6-benzyloxyamino-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester

Chemical Property of Benzoic acid (3aR,4R,6R,6aS)-6-benzyloxyamino-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (3aR,4R,6R,6aS)-6-benzyloxyamino-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester

There total 5 articles about Benzoic acid (3aR,4R,6R,6aS)-6-benzyloxyamino-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester 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: 42.0%

Benzoic acid (S)-1-[(4S,5S)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-bromo-ethyl ester (138946-51-7,138946-52-8) → Benzoic acid (3aR,4R,6R,6aS)-6-benzyloxyamino-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester (138946-58-4) + (4S,5R)-2,2-Dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde O-benzyl-oxime + (4S,5R)-2,2-Dimethyl-5-vinyl-[1,3]dioxolane-4-carbaldehyde O-benzyl-oxime

Guidance literature:

With samarium diiodide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; at -40 - -5 ℃; for 2.5h; Yields of byproduct given; further reagent; tributyltin hydride, AIBN;

DOI:10.1021/jo970987w

Reference yield:

Benzoic acid (S)-1-[(4S,5S)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-bromo-ethyl ester (138946-51-7,138946-52-8) → Benzoic acid (3aR,4R,6R,6aS)-6-benzyloxyamino-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester (138946-58-4) + Benzoic acid (3aR,4R,6S,6aS)-6-benzyloxyamino-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester (139015-09-1)

Guidance literature:

With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 2h; Yield given. Yields of byproduct given. Title compound not separated from byproducts; Heating;

DOI:10.1016/S0957-4166(00)86136-4

Reference yield:

O-benzylhydoxylamine hydrochloride (2687-43-6) → Benzoic acid (3aR,4R,6R,6aS)-6-benzyloxyamino-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl ester (138946-58-4)

Guidance literature:

Multi-step reaction with 3 steps

1: pyridine / CH₂Cl₂ / Heating

2: pyridine / Ambient temperature

3: tributyltin hydride, AIBN / toluene / 1) 5.5 h; 2) reflux, 5 h

With pyridine; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In dichloromethane; toluene;

DOI:10.1021/jo970987w

upstream raw materials:

Benzoic acid (S)-1-[(4S,5S)-5-(benzyloxyimino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-bromo-ethyl ester

O-benzylhydoxylamine hydrochloride

(3R,4S,5S)-5-(bromomethyl)-3,4-O-isopropylidenetetrahydrofuran-2,3,4-triol

5-bromo-2,3-O-isopropylidene-2,3,4-trihydroxypentanal-O-benzyl oxime