(2S,3S,4S)-N-carbobenzyloxy-2-methyl-2-(carboxycyclopropyl)glycine

Base Information

• Chemical Name: (2S,3S,4S)-N-carbobenzyloxy-2-methyl-2-(carboxycyclopropyl)glycine
• CAS No.: 537040-14-5
• Molecular Formula: C₁₅H₁₇NO₆
• Molecular Weight: 307.303
• Mol file: 537040-14-5.mol

Synonyms:(2S,3S,4S)-N-carbobenzyloxy-2-methyl-2-(carboxycyclopropyl)glycine

Chemical Property of (2S,3S,4S)-N-carbobenzyloxy-2-methyl-2-(carboxycyclopropyl)glycine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4S)-N-carbobenzyloxy-2-methyl-2-(carboxycyclopropyl)glycine

There total 3 articles about (2S,3S,4S)-N-carbobenzyloxy-2-methyl-2-(carboxycyclopropyl)glycine 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: 100.0%

(2R,4S)-4-((R)-2-Methoxycarbonyl-cyclopropyl)-4-methyl-5-oxo-2-phenyl-oxazolidine-3-carboxylic acid benzyl ester → (2S,3S,4S)-N-carbobenzyloxy-2-methyl-2-(carboxycyclopropyl)glycine (537040-14-5)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; water; at 25 ℃;

DOI:10.1016/S0957-4166(03)00049-1

Reference yield:

(2R,4R)-3-<(Benzyloxy)carbonyl>-4-methyl-2-phenyl-1,3-oxazolidin-5-one (135923-86-3,135923-87-4,143564-89-0) → (2S,3S,4S)-N-carbobenzyloxy-2-methyl-2-(carboxycyclopropyl)glycine (537040-14-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: KHMDS / tetrahydrofuran / 0.75 h / -78 °C

1.2: 62 percent / tetrahydrofuran / 0.75 h / -78 °C

2.1: 67 percent / Pd(OAc)2 / diethyl ether / 20 °C

3.1: 100 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 25 °C

With lithium hydroxide; potassium hexamethylsilazane; palladium diacetate; In tetrahydrofuran; diethyl ether; water;

DOI:10.1016/S0957-4166(03)00049-1

Reference yield:

(2R,4S)-2-phenyl-3-(carbobenzyloxy)-4-methyl-4-[(3-methoxy)carbonyl-(1E)-propenyl]oxazolidin-5-one (537040-12-3) → (2S,3S,4S)-N-carbobenzyloxy-2-methyl-2-(carboxycyclopropyl)glycine (537040-14-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 67 percent / Pd(OAc)2 / diethyl ether / 20 °C

2: 100 percent / LiOH*H₂O / tetrahydrofuran; H₂O / 25 °C

With lithium hydroxide; palladium diacetate; In tetrahydrofuran; diethyl ether; water;

DOI:10.1016/S0957-4166(03)00049-1

upstream raw materials:

(2R,4R)-3-<(Benzyloxy)carbonyl>-4-methyl-2-phenyl-1,3-oxazolidin-5-one

(2R,4S)-2-phenyl-3-(carbobenzyloxy)-4-methyl-4-[(3-methoxy)carbonyl-(1E)-propenyl]oxazolidin-5-one

Downstream raw materials:

(2S,3S,4S)-2-methyl-2-(carboxycyclopropyl)glycine