(2S,4S)-Methyl 4-acetoxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate

Base Information

• Chemical Name: (2S,4S)-Methyl 4-acetoxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate
• CAS No.: 128359-95-5
• Molecular Formula: C₁₄H₂₅NO₆Si
• Molecular Weight: 331.441
• Mol file: 128359-95-5.mol

Synonyms:(2S,4S)-Methyl 4-acetoxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate

Chemical Property of (2S,4S)-Methyl 4-acetoxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-Methyl 4-acetoxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate

There total 1 articles about (2S,4S)-Methyl 4-acetoxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate 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:

L-4-hydroxyproline methyl ester hydrochloride (40216-83-9) → (2S,4S)-Methyl 4-acetoxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate (128359-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 82 percent / Et₃N / acetonitrile / 16 h / Ambient temperature

2: 63 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 16 h / 25 °C

With triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; acetonitrile;

DOI:10.1021/jo00304a035

Reference yield: 56.0%

O-benzyl 2,2,2-trichloroacetimidate (81927-55-1) + (2S,4S)-Methyl 4-acetoxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate (128359-95-5) → (2S,4S)-4-acetoxy-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-phenylmethyl diester (128359-96-6)

Guidance literature:

With trifluorormethanesulfonic acid; In cyclohexane; for 1h;

DOI:10.1021/jo00304a035

Reference yield:

(2S,4S)-Methyl 4-acetoxy-1-<<2-(trimethylsilyl)ethyl>oxycarbonyl>pyrrolidine-2-carboxylate (128359-95-5) → (2S,4S,5R)-4-<(2-acetamido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranosyl)oxy>-5-<(benzyloxy)methyl>-1,2-pyrrolidinedicarboxylic acid bis(phenylmethyl ester) (129001-57-6)

Guidance literature:

Multi-step reaction with 11 steps

1: 1) Et₄NOTs, 2) Ac₂O, Et₃N / 1) graphite electrodes, 5.5 F mol^-1, 2) CH₂Cl₂

2: 77 percent / AcOH, H₂SO₄

3: 86 percent / TsOH

4: 67 percent / (Bu₃Sn)2 / benzene / Irradiation

5: 82 percent / TFA, aq. NaHCO₃ / CH₂Cl₂

6: 1) O₃, 2) NaBH₄ / 1) MeOH, CH₂Cl₂

7: 91 percent / Ag₂O / CH₂Cl₂ / Heating

8: 72 percent / Ti(O-i-Pr)4 / 110 °C

9: 42 percent / BF₃*Et₂O, 4-Angstroem sieves / -40 °C

10: 80 percent

11: 74 percent / KOH, H₂O, MeOH

With methanol; potassium hydroxide; sodium tetrahydroborate; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; water; bis(tri-n-butyltin); acetic anhydride; sodium hydrogencarbonate; tetraethylammonium tosylate; toluene-4-sulfonic acid; ozone; acetic acid; triethylamine; trifluoroacetic acid; silver(l) oxide; titanium(IV) isopropylate; In dichloromethane; benzene;

DOI:10.1021/jo00305a007

upstream raw materials:

L-4-hydroxyproline methyl ester hydrochloride

Downstream raw materials:

(2S,4S)-4-acetoxy-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-phenylmethyl diester

(2S,4S,5R)-4-hydroxy-5-(hydroxymethyl)pyrrolidine-2-carboxylic acid

(5R,4S,2S)-4-acetoxy-5-(hydroxymethyl)-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester

(5R,4S,2S)-4-acetoxy-5-<(E)-1-<2-(methoxycarbonyl)ethenyl>>-1,2-pyrrolidinedicarboxylic acid 2-methyl 1-(phenylmethyl) diester