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

Base Information

Chemical Name:(S)-2-((E)-(1R,2R)-2-Acetoxy-4-methoxycarbonyl-4-methoxycarbonylamino-1-phenylacetoxy-but-3-enyl)-aziridine-1-carboxylic acid benzyl ester
CAS No.:213454-21-8
Molecular Formula:C₂₈H₃₀N₂O₁₀
Molecular Weight:554.554
Hs Code.:

Synonyms:(S)-2-((E)-(1R,2R)-2-Acetoxy-4-methoxycarbonyl-4-methoxycarbonylamino-1-phenylacetoxy-but-3-enyl)-aziridine-1-carboxylic acid benzyl ester

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Chemical Property of (S)-2-((E)-(1R,2R)-2-Acetoxy-4-methoxycarbonyl-4-methoxycarbonylamino-1-phenylacetoxy-but-3-enyl)-aziridine-1-carboxylic acid benzyl ester

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Technology Process of (S)-2-((E)-(1R,2R)-2-Acetoxy-4-methoxycarbonyl-4-methoxycarbonylamino-1-phenylacetoxy-but-3-enyl)-aziridine-1-carboxylic acid benzyl ester

There total 8 articles about (S)-2-((E)-(1R,2R)-2-Acetoxy-4-methoxycarbonyl-4-methoxycarbonylamino-1-phenylacetoxy-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

: 213454-21-8
(S)-2-((E)-(1R,2R)-2-Acetoxy-4-methoxycarbonyl-4-methoxycarbonylamino-1-phenylacetoxy-but-3-enyl)-aziridine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 9 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: 99 percent / KO-t-Bu / tetrahydrofuran / -43 °C

8.1: O₃

8.2: (CH₃)2S

9.1: LiCl; i-Pr₂NEt / acetonitrile

With dmap; camphor-10-sulfonic acid; hydrogen fluoride; potassium tert-butylate; ozone; ethylene glycol; triethylamine; N-ethyl-N,N-diisopropylamine; 2`,3`-dideoxycytidine; lithium chloride; magnesium bromide; In tetrahydrofuran; 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: Cyclization / 8.1: ozonization / 8.2: Reduction / 9.1: olefination;
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

: 213454-21-8
(S)-2-((E)-(1R,2R)-2-Acetoxy-4-methoxycarbonyl-4-methoxycarbonylamino-1-phenylacetoxy-but-3-enyl)-aziridine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: Et₃N

2.1: DDC; DMAP

3.1: HF

4.1: Et₃N

5.1: 99 percent / KO-t-Bu / tetrahydrofuran / -43 °C

6.1: O₃

6.2: (CH₃)2S

7.1: LiCl; i-Pr₂NEt / acetonitrile

With dmap; hydrogen fluoride; potassium tert-butylate; ozone; triethylamine; N-ethyl-N,N-diisopropylamine; 2`,3`-dideoxycytidine; lithium chloride; In tetrahydrofuran; acetonitrile; 1.1: mesylation / 2.1: Esterification / 3.1: desilylation / 4.1: Acetylation / 5.1: Cyclization / 6.1: ozonization / 6.2: Reduction / 7.1: olefination;
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

: 213454-21-8
(S)-2-((E)-(1R,2R)-2-Acetoxy-4-methoxycarbonyl-4-methoxycarbonylamino-1-phenylacetoxy-but-3-enyl)-aziridine-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 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: 99 percent / KO-t-Bu / tetrahydrofuran / -43 °C

7.1: O₃

7.2: (CH₃)2S

8.1: LiCl; i-Pr₂NEt / acetonitrile

With dmap; camphor-10-sulfonic acid; hydrogen fluoride; potassium tert-butylate; ozone; ethylene glycol; triethylamine; N-ethyl-N,N-diisopropylamine; 2`,3`-dideoxycytidine; lithium chloride; In tetrahydrofuran; acetonitrile; 1.1: Ring cleavage / 2.1: mesylation / 3.1: Esterification / 4.1: desilylation / 5.1: Acetylation / 6.1: Cyclization / 7.1: ozonization / 7.2: Reduction / 8.1: olefination;
DOI:10.1021/ja992274w