(S)-2-[(E)-(1R,2R)-2-Acetoxy-1-(2-methoxy-acetoxy)-pent-3-enyl]-aziridine-1-carboxylic acid benzyl ester

Base Information

• Chemical Name: (S)-2-[(E)-(1R,2R)-2-Acetoxy-1-(2-methoxy-acetoxy)-pent-3-enyl]-aziridine-1-carboxylic acid benzyl ester
• CAS No.: 250735-64-9
• Molecular Formula: C₂₀H₂₅NO₇
• Molecular Weight: 391.421
• Mol file: 250735-64-9.mol

Synonyms:(S)-2-[(E)-(1R,2R)-2-Acetoxy-1-(2-methoxy-acetoxy)-pent-3-enyl]-aziridine-1-carboxylic acid benzyl ester

Chemical Property of (S)-2-[(E)-(1R,2R)-2-Acetoxy-1-(2-methoxy-acetoxy)-pent-3-enyl]-aziridine-1-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-[(E)-(1R,2R)-2-Acetoxy-1-(2-methoxy-acetoxy)-pent-3-enyl]-aziridine-1-carboxylic acid benzyl ester

There total 8 articles about (S)-2-[(E)-(1R,2R)-2-Acetoxy-1-(2-methoxy-acetoxy)-pent-3-enyl]-aziridine-1-carboxylic acid benzyl 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: 99.0%

Methoxy-acetic acid (E)-(1R,2R)-2-acetoxy-1-((R)-1-benzyloxycarbonylamino-2-iodo-ethyl)-pent-3-enyl ester (250735-63-8) → (S)-2-[(E)-(1R,2R)-2-Acetoxy-1-(2-methoxy-acetoxy)-pent-3-enyl]-aziridine-1-carboxylic acid benzyl ester (250735-64-9)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran; at -43 ℃;

DOI:10.1021/ja992274w

Reference yield:

(4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde (117833-92-8) → (S)-2-[(E)-(1R,2R)-2-Acetoxy-1-(2-methoxy-acetoxy)-pent-3-enyl]-aziridine-1-carboxylic acid benzyl ester (250735-64-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: MgBr₂*Et₂O / -20 °C

1.2: 95 percent / CH₂Cl₂ / 25 °C

2.1: 93 percent / camphorsulfonic acid; ethylene glycol / tetrahydrofuran / 50 °C

3.1: Et₃N

4.1: DDC; DMAP

5.1: HF

6.1: Et₃N

7.1: 89 percent / NaI

8.1: 99 percent / KO-t-Bu / tetrahydrofuran / -43 °C

With dmap; camphor-10-sulfonic acid; hydrogen fluoride; potassium tert-butylate; ethylene glycol; triethylamine; 2`,3`-dideoxycytidine; sodium iodide; magnesium bromide; In tetrahydrofuran; 1.1: complexation / 1.2: Addition / 2.1: Ring cleavage / 3.1: mesylation / 4.1: Esterification / 5.1: desilylation / 6.1: Acetylation / 7.1: Iodination / 8.1: Cyclization;

DOI:10.1021/ja992274w

Reference yield:

[(E)-(1S,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-1-hydroxymethyl-hex-4-enyl]-carbamic acid benzyl ester (213454-12-7) → (S)-2-[(E)-(1R,2R)-2-Acetoxy-1-(2-methoxy-acetoxy)-pent-3-enyl]-aziridine-1-carboxylic acid benzyl ester (250735-64-9)

Guidance literature:

Multi-step reaction with 6 steps

1: Et₃N

2: DDC; DMAP

3: HF

4: Et₃N

5: 89 percent / NaI

6: 99 percent / KO-t-Bu / tetrahydrofuran / -43 °C

With dmap; hydrogen fluoride; potassium tert-butylate; triethylamine; 2`,3`-dideoxycytidine; sodium iodide; In tetrahydrofuran; 1: mesylation / 2: Esterification / 3: desilylation / 4: Acetylation / 5: Iodination / 6: Cyclization;

DOI:10.1021/ja992274w

upstream raw materials:

Methoxy-acetic acid (E)-(1R,2R)-2-acetoxy-1-((R)-1-benzyloxycarbonylamino-2-iodo-ethyl)-pent-3-enyl ester

(4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde

[(E)-(1S,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-1-hydroxymethyl-hex-4-enyl]-carbamic acid benzyl ester

(S)-4-[(E)-(1R,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-pent-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

Downstream raw materials:

(S)-2-[(1R,2S)-2-Acetoxy-1-(2-methoxy-acetoxy)-3-oxo-propyl]-aziridine-1-carboxylic acid benzyl ester

(S)-2-((E)-(1R,2S)-2-Acetoxy-4-acetylamino-3-bromo-1-hydroxy-4-methoxycarbonyl-but-3-enyl)-aziridine-1-carboxylic acid benzyl ester

(S)-2-((E)-(1R,2S)-2-Acetoxy-4-acetylamino-3-bromo-4-methoxycarbonyl-1-trimethylsilanyloxy-but-3-enyl)-aziridine-1-carboxylic acid benzyl ester

(S)-2-[(E)-(1R,2S)-2-Acetoxy-4-acetylamino-3-bromo-1-(2-methoxy-acetoxy)-4-methoxycarbonyl-but-3-enyl]-aziridine-1-carboxylic acid benzyl ester