5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-formyl-8-oxo-7-[(2-thienylacetyl)amino]-, diphenylmethyl ester, (6R-trans)-

Base Information

Chemical Name:5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-formyl-8-oxo-7-[(2-thienylacetyl)amino]-, diphenylmethyl ester, (6R-trans)-
CAS No.:33741-82-1
Molecular Formula:C₂₇H₂₂N₂O₅S₂
Molecular Weight:518.614
Hs Code.:
NSC Number:687544
DSSTox Substance ID:DTXSID201102265
ChEMBL ID:CHEMBL1964963

Synonyms:NSC687544;CHEMBL1964963;SCHEMBL11586007;DTXSID201102265;NSC-687544;NCI60_031514;33741-82-1;5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-formyl-8-oxo-7-[(2-thienylacetyl)amino]-, diphenylmethyl ester, (6R-trans)-

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Chemical Property of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-formyl-8-oxo-7-[(2-thienylacetyl)amino]-, diphenylmethyl ester, (6R-trans)-

Chemical Property:

XLogP3:3.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:9
Exact Mass:518.09701415
Heavy Atom Count:36
Complexity:879

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Canonical SMILES:C1C(=C(N2C(S1)C(C2=O)NC(=O)CC3=CC=CS3)C(=O)OC(C4=CC=CC=C4)C5=CC=CC=C5)C=O
Isomeric SMILES:C1C(=C(N2[C@H](S1)[C@@H](C2=O)NC(=O)CC3=CC=CS3)C(=O)OC(C4=CC=CC=C4)C5=CC=CC=C5)C=O

Technology Process of 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-formyl-8-oxo-7-[(2-thienylacetyl)amino]-, diphenylmethyl ester, (6R-trans)-

There total 8 articles about 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-formyl-8-oxo-7-[(2-thienylacetyl)amino]-, diphenylmethyl ester, (6R-trans)- 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: 95.0%

: 53493-27-9
3-formyl-7-thienylacetamidoceph-3-em-4-carboxylic acid

: 908093-98-1
diazodiphenylmethane

: 33741-82-1
benzhydryl 3-formyl-7-thienylacetamidoceph-3-em-4-carboxylate

Guidance literature:: In tetrahydrofuran; for 0.5h; Ambient temperature;
DOI:10.1248/cpb.28.2116

Reference yield:

: N-(1-Oxo-7-trimethylsilanyloxy-2,2a-dihydro-1H,4H-6-oxa-3-thia-7b-aza-cyclobuta[e]inden-2-yl)-2-thiophen-2-yl-acetamide

: 33741-82-1
(6R)-3-formyl-8-oxo-7t-(2-thiophen-2-yl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Guidance literature:: Multi-step reaction with 3 steps

1: bromine / dimethylformamide / 0 °C

2: dimethylsulfoxide / Ambient temperature

3: tetrahydrofuran

With bromine; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1248/cpb.28.1339

Reference yield:

: 876026-57-2
N-((5aR)-1,7-dioxo-(5ar)-1,4,6,7-tetrahydro-3H,5aH-azeto[2,1-b]furo[3,4-d][1,3]thiazin-6t-yl)-2-thiophen-2-yl-acetamide

: 33741-82-1
(6R)-3-formyl-8-oxo-7t-(2-thiophen-2-yl-acetylamino)-(6rH)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Guidance literature:: Multi-step reaction with 4 steps

1: triethylamine / dimethylformamide / Ambient temperature

2: bromine / dimethylformamide / 0 °C

3: dimethylsulfoxide / Ambient temperature

4: tetrahydrofuran

With bromine; triethylamine; In tetrahydrofuran; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1248/cpb.28.1339