(1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[2-thioxopyrrolidin-4(R)-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid isobutyryloxymethyl ester

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Chemical Name:(1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[2-thioxopyrrolidin-4(R)-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid isobutyryloxymethyl ester
CAS No.:141628-82-2
Molecular Formula:C₁₉H₂₆N₂O₆S₂
Molecular Weight:442.557
Hs Code.:

(1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[2-thioxopyrrolidin-4(R)-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid isobutyryloxymethyl ester

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Chemical Property of (1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[2-thioxopyrrolidin-4(R)-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid isobutyryloxymethyl ester

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Technology Process of (1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[2-thioxopyrrolidin-4(R)-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid isobutyryloxymethyl ester

There total 4 articles about (1R,5S,6S)-6-[1(R)-Hydroxyethyl]-1-methyl-2-[2-thioxopyrrolidin-4(R)-ylsulfanyl]-1-carba-2-penem-3-carboxylic acid isobutyryloxymethyl 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: 83.0%

: 63379-62-4
isobutyryloxymethyl iodide

: sodium (4R,5R,6S)-6-[(R)-1-(hydroxy)ethyl]-3-[(R)-pyrrolidine-2-thion-4-ylthio]-4-methyl-7-oxo-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

: 141628-82-2
TA-949

Guidance literature:: With 1-methyl-pyrrolidin-2-one; 4 A molecular sieve; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at -15 - -10 ℃; for 1.5h;
DOI:10.1021/jo991461+

Reference yield:

: 153471-13-7
allyl (4R,5R,6S)-6-[(R)-1-(hydroxy)ethyl]-3-[(R)-pyrrolidine-2-thion-4-ylthio]-4-methyl-7-oxo-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

: 141628-82-2
TA-949

Guidance literature:: Multi-step reaction with 2 steps

1: 87 percent / NaHCO₃; dimedone; Pd(OAc)3, P(OEt)3 / tetrahydrofuran; H₂O / 0.75 h / 35 - 37 °C

2: 83 percent / 4 Angstroem molecular sieves; N-methylpyrrolidone; DIPEA / dimethylformamide / 1.5 h / -15 - -10 °C

With 1-methyl-pyrrolidin-2-one; palladium(III) acetate; 4 A molecular sieve; sodium hydrogencarbonate; dimedone; N-ethyl-N,N-diisopropylamine; triethyl phosphite; In tetrahydrofuran; water; N,N-dimethyl-formamide; 1: Hydrolysis / 2: Esterification;
DOI:10.1021/jo991461+

Reference yield:

: 153471-14-8
allyl (4R,5R,6S)-6-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-3-[(R)-pyrrolidine-2-thion-4-ylthio]-4-methyl-7-oxo-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

: 141628-82-2
TA-949

Guidance literature:: Multi-step reaction with 3 steps

1: 90 percent / NH₄F*HF; N-methylpyrrolidone / dimethylformamide / 108 h / 20 °C

2: 87 percent / NaHCO₃; dimedone; Pd(OAc)3, P(OEt)3 / tetrahydrofuran; H₂O / 0.75 h / 35 - 37 °C

3: 83 percent / 4 Angstroem molecular sieves; N-methylpyrrolidone; DIPEA / dimethylformamide / 1.5 h / -15 - -10 °C

With 1-methyl-pyrrolidin-2-one; ammonium fluoride; palladium(III) acetate; 4 A molecular sieve; hydrogen fluoride; sodium hydrogencarbonate; dimedone; N-ethyl-N,N-diisopropylamine; triethyl phosphite; In tetrahydrofuran; water; N,N-dimethyl-formamide; 1: Substitution / 2: Hydrolysis / 3: Esterification;
DOI:10.1021/jo991461+