(2S,4S)-N-allyloxycarbonyl-2-[(Z)-3-allyloxycarbonylamino-1-propenyl]-4-tritylthiopyrrolidine

Base Information

Chemical Name:(2S,4S)-N-allyloxycarbonyl-2-[(Z)-3-allyloxycarbonylamino-1-propenyl]-4-tritylthiopyrrolidine
CAS No.:147505-57-5
Molecular Formula:C₃₄H₃₆N₂O₄S
Molecular Weight:568.737
Hs Code.:

Synonyms:(2S,4S)-N-allyloxycarbonyl-2-[(Z)-3-allyloxycarbonylamino-1-propenyl]-4-tritylthiopyrrolidine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2S,4S)-N-allyloxycarbonyl-2-[(Z)-3-allyloxycarbonylamino-1-propenyl]-4-tritylthiopyrrolidine

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Technology Process of (2S,4S)-N-allyloxycarbonyl-2-[(Z)-3-allyloxycarbonylamino-1-propenyl]-4-tritylthiopyrrolidine

There total 9 articles about (2S,4S)-N-allyloxycarbonyl-2-[(Z)-3-allyloxycarbonylamino-1-propenyl]-4-tritylthiopyrrolidine 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: 73.0%

: 2937-50-0
Allyl chloroformate

: 1027894-06-9
(3S,5S)-N-allyloxycarbonyl-5-[(Z)-3-azido-1-propenyl]-3-tritylthiopyrrolidine

: 147505-57-5
(2S,4S)-N-allyloxycarbonyl-2-[(Z)-3-allyloxycarbonylamino-1-propenyl]-4-tritylthiopyrrolidine

Guidance literature:: With triethylamine; triphenylphosphine; In tetrahydrofuran; water; at 20 ℃;
DOI:10.7164/antibiotics.50.586

Reference yield:

: 3695-77-0
triphenylmethanethiol

: 147505-57-5
(2S,4S)-N-allyloxycarbonyl-2-[(Z)-3-allyloxycarbonylamino-1-propenyl]-4-tritylthiopyrrolidine

Guidance literature:: Multi-step reaction with 8 steps

1: 70 percent / NaH / dimethylformamide / 3.5 h / 4 - 20 °C

2: 77 percent / LiCl; NaBH₄ / tetrahydrofuran; ethanol / 17 h / 4 °C

3: oxalyl chloride; NEt₃ / CH₂Cl₂; dimethylsulfoxide / 1.33 h / -78 - 0 °C

4: 75 percent / 18-crown-6; KN(TMS)2 / tetrahydrofuran; toluene / 1.5 h / -78 °C

5: 49 percent / DIBAL-H / toluene / 1.3 h / -78 °C

6: NEt₃ / tetrahydrofuran / 0.5 h / 4 °C

7: 93 percent / NaN₃ / dimethylformamide / 1 h / 50 °C

8: 73 percent / PPh₃; NEt₃ / tetrahydrofuran; H₂O / 20 °C

With sodium tetrahydroborate; sodium azide; oxalyl dichloride; 18-crown-6 ether; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Reduction / 3: Swern oxidation / 4: Horner -Emmons reaction / 5: Reduction / 6: Substitution / 7: Substitution / 8: Substitution;
DOI:10.7164/antibiotics.50.586

Reference yield:

: 126408-14-8
methyl (2S,4R)-N-(allyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylate

: 147505-57-5
(2S,4S)-N-allyloxycarbonyl-2-[(Z)-3-allyloxycarbonylamino-1-propenyl]-4-tritylthiopyrrolidine

Guidance literature:: Multi-step reaction with 9 steps

1: NEt₃ / tetrahydrofuran / 0.5 h / 4 °C

2: 70 percent / NaH / dimethylformamide / 3.5 h / 4 - 20 °C

3: 77 percent / LiCl; NaBH₄ / tetrahydrofuran; ethanol / 17 h / 4 °C

4: oxalyl chloride; NEt₃ / CH₂Cl₂; dimethylsulfoxide / 1.33 h / -78 - 0 °C

5: 75 percent / 18-crown-6; KN(TMS)2 / tetrahydrofuran; toluene / 1.5 h / -78 °C

6: 49 percent / DIBAL-H / toluene / 1.3 h / -78 °C

7: NEt₃ / tetrahydrofuran / 0.5 h / 4 °C

8: 93 percent / NaN₃ / dimethylformamide / 1 h / 50 °C

9: 73 percent / PPh₃; NEt₃ / tetrahydrofuran; H₂O / 20 °C

With sodium tetrahydroborate; sodium azide; oxalyl dichloride; 18-crown-6 ether; potassium hexamethylsilazane; sodium hydride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; lithium chloride; In tetrahydrofuran; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; 1: Substitution / 2: Substitution / 3: Reduction / 4: Swern oxidation / 5: Horner -Emmons reaction / 6: Reduction / 7: Substitution / 8: Substitution / 9: Substitution;
DOI:10.7164/antibiotics.50.586