(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

Base Information

Chemical Name:(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
CAS No.:250735-69-4
Molecular Formula:C₂₃H₂₇BrN₂O₁₀
Molecular Weight:571.379
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 12 articles about (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 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:

: 117833-92-8
(4S)-3-benzyloxycarbonyl-2,2-dimethyloxazolidine-4-carbaldehyde

: 250735-69-4
(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

Guidance literature:: Multi-step reaction with 12 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

9.1: O₃

9.2: (CH₃)2S

10.1: LiCl; i-Pr₂NEt / acetonitrile

11.1: N-bromosuccinimide / CHCl₃ / 40 °C

12.1: base

With dmap; N-Bromosuccinimide; camphor-10-sulfonic acid; hydrogen fluoride; potassium tert-butylate; ozone; ethylene glycol; triethylamine; N-ethyl-N,N-diisopropylamine; 2`,3`-dideoxycytidine; sodium iodide; lithium chloride; magnesium bromide; In tetrahydrofuran; chloroform; acetonitrile; 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 / 9.1: ozonization / 9.2: Reduction / 10.1: olefination / 11.1: Bromination / 12.1: tautomerization;
DOI:10.1021/ja992274w

Reference yield:

: 213454-12-7
[(E)-(1S,2R,3R)-3-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxy-1-hydroxymethyl-hex-4-enyl]-carbamic acid benzyl ester

: 250735-69-4
(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

Guidance literature:: Multi-step reaction with 10 steps

1.1: Et₃N

2.1: DDC; DMAP

3.1: HF

4.1: Et₃N

5.1: 89 percent / NaI

6.1: 99 percent / KO-t-Bu / tetrahydrofuran / -43 °C

7.1: O₃

7.2: (CH₃)2S

8.1: LiCl; i-Pr₂NEt / acetonitrile

9.1: N-bromosuccinimide / CHCl₃ / 40 °C

10.1: base

With dmap; N-Bromosuccinimide; hydrogen fluoride; potassium tert-butylate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; 2`,3`-dideoxycytidine; sodium iodide; lithium chloride; In tetrahydrofuran; chloroform; acetonitrile; 1.1: mesylation / 2.1: Esterification / 3.1: desilylation / 4.1: Acetylation / 5.1: Iodination / 6.1: Cyclization / 7.1: ozonization / 7.2: Reduction / 8.1: olefination / 9.1: Bromination / 10.1: tautomerization;
DOI:10.1021/ja992274w

Reference yield:

: 213454-11-6
(S)-4-[(E)-(1R,2R)-2-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-pent-3-enyl]-2,2-dimethyl-oxazolidine-3-carboxylic acid benzyl ester

: 250735-69-4
(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

Guidance literature:: Multi-step reaction with 11 steps

1.1: 93 percent / camphorsulfonic acid; ethylene glycol / tetrahydrofuran / 50 °C

2.1: Et₃N

3.1: DDC; DMAP

4.1: HF

5.1: Et₃N

6.1: 89 percent / NaI

7.1: 99 percent / KO-t-Bu / tetrahydrofuran / -43 °C

8.1: O₃

8.2: (CH₃)2S

9.1: LiCl; i-Pr₂NEt / acetonitrile

10.1: N-bromosuccinimide / CHCl₃ / 40 °C

11.1: base

With dmap; N-Bromosuccinimide; camphor-10-sulfonic acid; hydrogen fluoride; potassium tert-butylate; ozone; ethylene glycol; triethylamine; N-ethyl-N,N-diisopropylamine; 2`,3`-dideoxycytidine; sodium iodide; lithium chloride; In tetrahydrofuran; chloroform; acetonitrile; 1.1: Ring cleavage / 2.1: mesylation / 3.1: Esterification / 4.1: desilylation / 5.1: Acetylation / 6.1: Iodination / 7.1: Cyclization / 8.1: ozonization / 8.2: Reduction / 9.1: olefination / 10.1: Bromination / 11.1: tautomerization;
DOI:10.1021/ja992274w