4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-ethynyl-6-hydroxy-3,3-dimethyl-7-oxo-, phenylmethyl ester, [2S-(2alpha,5alpha,6beta)]-

Base Information

Chemical Name:4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-ethynyl-6-hydroxy-3,3-dimethyl-7-oxo-, phenylmethyl ester, [2S-(2alpha,5alpha,6beta)]-
CAS No.:121534-37-0
Molecular Formula:C₁₇H₁₇NO₄S
Molecular Weight:331.392
Hs Code.:
DSSTox Substance ID:DTXSID201102710

4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-ethynyl-6-hydroxy-3,3-dimethyl-7-oxo-, phenylmethyl ester, [2S-(2alpha,5alpha,6beta)]-

Synonyms:DTXSID201102710;121534-37-0;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-ethynyl-6-hydroxy-3,3-dimethyl-7-oxo-, phenylmethyl ester, [2S-(2alpha,5alpha,6beta)]-

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Chemical Property of 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-ethynyl-6-hydroxy-3,3-dimethyl-7-oxo-, phenylmethyl ester, [2S-(2alpha,5alpha,6beta)]-

Chemical Property:

XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:5
Exact Mass:331.08782920
Heavy Atom Count:23
Complexity:574

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:CC1(C(N2C(S1)C(C2=O)(C#C)O)C(=O)OCC3=CC=CC=C3)C
Isomeric SMILES:CC1([C@@H](N2[C@H](S1)[C@](C2=O)(C#C)O)C(=O)OCC3=CC=CC=C3)C

Technology Process of 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-ethynyl-6-hydroxy-3,3-dimethyl-7-oxo-, phenylmethyl ester, [2S-(2alpha,5alpha,6beta)]-

There total 5 articles about 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-ethynyl-6-hydroxy-3,3-dimethyl-7-oxo-, phenylmethyl ester, [2S-(2alpha,5alpha,6beta)]- 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: 62.0%

: 94340-07-5
Ethynylcerium(III) dichloride

: 39126-59-5
6-oxopenicillanic acid benzyl ester

: 121534-37-0
benzyl 6α-ethynyl-6β-hydroxypenicillinate

Guidance literature:: with magnesium acetylide;
DOI:10.1016/S0040-4039(00)80677-2

Reference yield:

: 551-16-6
6-Aminopenicillanic Acid

: 121534-37-0
benzyl 6α-ethynyl-6β-hydroxypenicillinate

Guidance literature:: Multi-step reaction with 4 steps

1: 32 percent / 70percent HClO₄, NaNO₂ / H₂O / 0.33 h / -5 - 0 °C

2: 1) Et₃N / 1) DMF, 0 deg C, 2) rt, overnight

3: 98 percent / trifluoroacetic anhydride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

With perchloric acid; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; sodium nitrite; In dichloromethane; water;
DOI:10.1021/jo00058a008

Reference yield:

: 15058-64-7
6-α-hydroxypenicillanic acid

: 121534-37-0
benzyl 6α-ethynyl-6β-hydroxypenicillinate

Guidance literature:: Multi-step reaction with 3 steps

1: 1) Et₃N / 1) DMF, 0 deg C, 2) rt, overnight

2: 98 percent / trifluoroacetic anhydride, dimethyl sulfoxide / CH₂Cl₂ / 1 h / -78 °C

With dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In dichloromethane;
DOI:10.1021/jo00058a008