racemic 5(R)-1-aza-4(R)-carboxy-6(R)-hydroxy-4(R)-(phenylseleno)bicyclo<3.3.0>octane lactone

Base Information

Chemical Name:racemic 5(R)-1-aza-4(R)-carboxy-6(R)-hydroxy-4(R)-(phenylseleno)bicyclo<3.3.0>octane lactone
CAS No.:85365-61-3
Molecular Formula:C₁₄H₁₅NO₂Se
Molecular Weight:308.239
Hs Code.:

Synonyms:

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Chemical Property of racemic 5(R)-1-aza-4(R)-carboxy-6(R)-hydroxy-4(R)-(phenylseleno)bicyclo<3.3.0>octane lactone

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Technology Process of racemic 5(R)-1-aza-4(R)-carboxy-6(R)-hydroxy-4(R)-(phenylseleno)bicyclo<3.3.0>octane lactone

There total 30 articles about racemic 5(R)-1-aza-4(R)-carboxy-6(R)-hydroxy-4(R)-(phenylseleno)bicyclo<3.3.0>octane lactone 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: 92.0%

: C₁₇H₂₁NOS₂Se

: 85365-61-3,98717-29-4
racemic 5(R)-1-aza-4(R)-carboxy-6(R)-hydroxy-4(R)-(phenylseleno)bicyclo<3.3.0>octane lactone

Guidance literature:: With calcium carbonate; mercury dichloride; In water; acetonitrile; for 0.5h; Ambient temperature;
DOI:10.1021/jo00223a002

Reference yield:

: 25471-73-2
7-Oxo-8α-pyrrolizidin-1α-carbonsaeure-methylester

: 85365-61-3,98717-29-4
5(R)-1-aza-4(R)-carboxy-6(R)-hydroxy-4(R)-(phenylseleno)bicyclo<3.3.0>octane lactone

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / H₂ / PtO₂ / methanol / 1.5 h / 760 Torr / Ambient temperature

2: 75 percent / EtONa, 3-A molecular sieve / ethanol / 2.5 h / Heating

3: 1.) LDA / 1.) THF, -70 deg C, 1.5 h, 2.) a) THF, -70 deg C, 1 h, b) -40 deg C, 1.5 h

With 3 A molecular sieve; hydrogen; sodium ethanolate; lithium diisopropyl amide; platinum(IV) oxide; In methanol; ethanol;
DOI:10.1021/jo00223a002

Reference yield:

: 85319-62-6
1-aza-4-(1,3-dithian-2-ylidene)-6(S)-(acetyloxy)bicyclo<3.3.0>octan-8-one

: 85365-61-3,98717-29-4
5(R)-1-aza-4(R)-carboxy-6(R)-hydroxy-4(R)-(phenylseleno)bicyclo<3.3.0>octane lactone

Guidance literature:: Multi-step reaction with 6 steps

1: 82 percent / LiAlH₄ / tetrahydrofuran / 2 h / Heating

2: 71 percent / aq. HCl, HgCl₂, trifluoroacetic acid / 8 h / Heating

3: 72 percent / trifluoroacetic anhydride, Me₂SO / CH₂Cl₂ / 1 h / -65 °C

4: 97 percent / H₂ / PtO₂ / methanol / 1.5 h / 760 Torr / Ambient temperature

5: 75 percent / EtONa, 3-A molecular sieve / ethanol / 2.5 h / Heating

6: 1.) LDA / 1.) THF, -70 deg C, 1.5 h, 2.) a) THF, -70 deg C, 1 h, b) -40 deg C, 1.5 h

With hydrogenchloride; lithium aluminium tetrahydride; 3 A molecular sieve; hydrogen; sodium ethanolate; dimethyl sulfoxide; trifluoroacetic acid; trifluoroacetic anhydride; mercury dichloride; lithium diisopropyl amide; platinum(IV) oxide; In tetrahydrofuran; methanol; ethanol; dichloromethane;
DOI:10.1021/jo00223a002