(+/-)-epi-benzyl 3-acetylamino-O-benzylnocardicinate

Base Information

• Chemical Name: (+/-)-epi-benzyl 3-acetylamino-O-benzylnocardicinate
• CAS No.: 75986-12-8
• Molecular Formula: C₂₇H₂₆N₂O₅
• Molecular Weight: 458.514
• Mol file: 75986-12-8.mol

Synonyms:

Chemical Property of (+/-)-epi-benzyl 3-acetylamino-O-benzylnocardicinate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (+/-)-epi-benzyl 3-acetylamino-O-benzylnocardicinate

There total 26 articles about (+/-)-epi-benzyl 3-acetylamino-O-benzylnocardicinate 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:

benzyl N-(2-bromo-2-propenyl)-p-benzyloxyphenylglycinate (75986-03-7) → (+/-)-benzyl 3-acetylamino-O-benzylnocardicinate (75986-12-8,75986-13-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 62.7 percent / 2 molpercent Pd(OAc)2, 8 molpercent PPh₃, 1.2 mol. equiv. Bu₃N / hexamethylphosphoric acid triamide / 38 h / 80 °C / 3040 Torr

2: 83 percent / OsO₄

3: 72.8 percent / NaIO₄

4: 65.4 percent / NH₂OH*HCl / pyridine

5: NaOAc

6: H₂ / PtO₂

With palladium diacetate; sodium periodate; osmium(VIII) oxide; tributyl-amine; hydroxylamine hydrochloride; hydrogen; sodium acetate; triphenylphosphine; platinum(IV) oxide; In pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1039/c39800000770

Reference yield:

benzyl N-(2-bromo-2-propenyl)-p-benzyloxyphenylglycinate (75986-03-7) → (+/-)-epi-benzyl 3-acetylamino-O-benzylnocardicinate (75986-12-8,75986-13-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 62.7 percent / 2 molpercent Pd(OAc)2, 8 molpercent PPh₃, 1.2 mol. equiv. Bu₃N / hexamethylphosphoric acid triamide / 38 h / 80 °C / 3040 Torr

2: 83 percent / OsO₄

3: 72.8 percent / NaIO₄

4: 65.4 percent / NH₂OH*HCl / pyridine

5: NaOAc

6: H₂ / PtO₂

With palladium diacetate; sodium periodate; osmium(VIII) oxide; tributyl-amine; hydroxylamine hydrochloride; hydrogen; sodium acetate; triphenylphosphine; platinum(IV) oxide; In pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1039/c39800000770

Reference yield:

α-amino-4-(phenylmethoxy)benzeneacetic acid phenylmethyl ester HCl (75986-02-6) → (+/-)-epi-benzyl 3-acetylamino-O-benzylnocardicinate (75986-12-8,75986-13-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 81.6 percent / K₂CO₃

2: 62.7 percent / 2 molpercent Pd(OAc)2, 8 molpercent PPh₃, 1.2 mol. equiv. Bu₃N / hexamethylphosphoric acid triamide / 38 h / 80 °C / 3040 Torr

3: 83 percent / OsO₄

4: 72.8 percent / NaIO₄

5: 65.4 percent / NH₂OH*HCl / pyridine

6: NaOAc

7: H₂ / PtO₂

With palladium diacetate; sodium periodate; osmium(VIII) oxide; tributyl-amine; hydroxylamine hydrochloride; hydrogen; sodium acetate; potassium carbonate; triphenylphosphine; platinum(IV) oxide; In pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1039/c39800000770

upstream raw materials:

acetic anhydride

(+/-)-dibenzyl 3-ANA

benzyl α-(3-hydroxyimino-2-oxo-1-azetidinyl)-p-benzyloxyphenylacetate

benzyl bromide

Refernces

• 1、 Chiba, Katsumi,Mori, Miwako,Ban, Yoshio. "A Novel Synthesis of (+/-)-3-Aminonocardinic Acid". . p. 770 - 772. Retrieved 2007/10/02.