cis-4-(R)-<6-(Methoxycarbonyl)hex-1-enyl>-2(R)-phenylthiazolidine-3-carboxylic acid methyl ester

Base Information

• Chemical Name: cis-4-(R)-<6-(Methoxycarbonyl)hex-1-enyl>-2(R)-phenylthiazolidine-3-carboxylic acid methyl ester
• CAS No.: 151415-02-0
• Molecular Formula: C₁₉H₂₅NO₄S
• Molecular Weight: 363.478

Synonyms:cis-4-(R)-<6-(Methoxycarbonyl)hex-1-enyl>-2(R)-phenylthiazolidine-3-carboxylic acid methyl ester

Chemical Property of cis-4-(R)-<6-(Methoxycarbonyl)hex-1-enyl>-2(R)-phenylthiazolidine-3-carboxylic acid methyl ester

Chemical Property:

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Technology Process of cis-4-(R)-<6-(Methoxycarbonyl)hex-1-enyl>-2(R)-phenylthiazolidine-3-carboxylic acid methyl ester

There total 4 articles about cis-4-(R)-<6-(Methoxycarbonyl)hex-1-enyl>-2(R)-phenylthiazolidine-3-carboxylic acid methyl 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%

diazomethane (186581-53-3,908094-01-9,334-88-3) + cis-4-(R)-<6-(Methoxycarbonyl)hex-1-enyl>-2(R)-phenylthiazolidine-3-carboxylic acid (1027086-34-5) → cis-4-(R)-<6-(Methoxycarbonyl)hex-1-enyl>-2(R)-phenylthiazolidine-3-carboxylic acid methyl ester (151415-02-0)

Guidance literature:

In diethyl ether; at 0 ℃;

DOI:10.1016/S0040-4039(00)79354-3 DOI:10.1021/jo00107a009

Reference yield:

(5-carboxypentyl)triphenylphosphonium bromide (50889-29-7) → cis-4-(R)-<6-(Methoxycarbonyl)hex-1-enyl>-2(R)-phenylthiazolidine-3-carboxylic acid methyl ester (151415-02-0)

Guidance literature:

Multi-step reaction with 2 steps

1: LDA / tetrahydrofuran; hexane / 1.) room temp., 30 min, 2.) room temp., 1 h

2: 99 percent / diethyl ether / 0 °C

With lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane;

DOI:10.1021/jo00107a009

Reference yield:

6-bromohexanoic acid (4224-70-8) → cis-4-(R)-<6-(Methoxycarbonyl)hex-1-enyl>-2(R)-phenylthiazolidine-3-carboxylic acid methyl ester (151415-02-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / acetonitrile / 16 h / Heating

2: LDA / tetrahydrofuran; hexane / 1.) room temp., 30 min, 2.) room temp., 1 h

3: 99 percent / diethyl ether / 0 °C

With lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; hexane; acetonitrile;

DOI:10.1021/jo00107a009

upstream raw materials:

diazomethane

cis-4-(R)-<6-(Methoxycarbonyl)hex-1-enyl>-2(R)-phenylthiazolidine-3-carboxylic acid

6-bromohexanoic acid

(5-carboxypentyl)triphenylphosphonium bromide

Downstream raw materials:

biotin

5-[(3aS,6aR)-1-Benzyl-2-oxo-hexahydro-thieno[3,4-d]imidazol-(4Z)-ylidene]-pentanoic acid methyl ester

N-(Phenylmethyl)-3(R)-bromo-2(R)-(carbomethoxybutyl)tetrahydrothiophene-4(S)-carbamoyl azide

Δ^2,3,N-(Phenylmethyl)-2-(carbomethoxybutyl)dihydrothiophene-4(S)-carbamoyl azide

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