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

Base Information

• Chemical Name: benzyl α-(3-hydroxy-3-hydroxymethyl-2-oxo-1-azetidinyl)-p-benzyloxyphenylacetate
• CAS No.: 75986-06-0
• Molecular Formula: C₂₆H₂₅NO₆
• Molecular Weight: 447.488
• Mol file: 75986-06-0.mol

Synonyms:benzyl α-(3-hydroxy-3-hydroxymethyl-2-oxo-1-azetidinyl)-p-benzyloxyphenylacetate

Chemical Property of benzyl α-(3-hydroxy-3-hydroxymethyl-2-oxo-1-azetidinyl)-p-benzyloxyphenylacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl α-(3-hydroxy-3-hydroxymethyl-2-oxo-1-azetidinyl)-p-benzyloxyphenylacetate

There total 7 articles about benzyl α-(3-hydroxy-3-hydroxymethyl-2-oxo-1-azetidinyl)-p-benzyloxyphenylacetate 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: 83.0%

benzyl α-(2-oxo-3-methylene-1-azetidinyl)-p-benzyloxyphenylacetate (75986-04-8) → benzyl α-(3-hydroxy-3-hydroxymethyl-2-oxo-1-azetidinyl)-p-benzyloxyphenylacetate (75986-06-0)

Guidance literature:

With N-ethylmorpholine N-oxide; osmium(VIII) oxide; In dichloromethane; water; acetone; tert-butyl alcohol; for 168h;

DOI:10.1016/S0040-4020(01)96430-0

Reference yield:

benzyl N-(2-bromo-2-propenyl)-p-benzyloxyphenylglycinate (75986-03-7) → benzyl α-(3-hydroxy-3-hydroxymethyl-2-oxo-1-azetidinyl)-p-benzyloxyphenylacetate (75986-06-0)

Guidance literature:

Multi-step reaction with 2 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

With palladium diacetate; osmium(VIII) oxide; tributyl-amine; triphenylphosphine; In 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) → benzyl α-(3-hydroxy-3-hydroxymethyl-2-oxo-1-azetidinyl)-p-benzyloxyphenylacetate (75986-06-0)

Guidance literature:

Multi-step reaction with 3 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

With palladium diacetate; osmium(VIII) oxide; tributyl-amine; potassium carbonate; triphenylphosphine; In N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1039/c39800000770

upstream raw materials:

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

benzyl bromide

p-hydroxyphenylglycine

benzyl N-(2-bromo-2-propenyl)-p-benzyloxyphenylglycinate

Downstream raw materials:

Benzyl (+/-)-(αR^*,3S^*)-3-Amino-α--2-oxo-1-azetidineacetate Hydrotosylate

Benzyl (+/-)-(αR^*,3R^*)-3-Amino-α--2-oxo-1-azetidineacetate Hydrotosylate

(+/-)-dibenzyl 3-ANA

(+/-)-epi-dibenzyl 3-ANA

Refernces

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