(3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2'-hydroxymethyl-5-thienylcarbonyl)methyl-azetidin-2-one

Base Information

• Chemical Name: (3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2'-hydroxymethyl-5-thienylcarbonyl)methyl-azetidin-2-one
• CAS No.: 88139-99-5
• Molecular Formula: C₄₇H₄₀N₃O₁₂PS
• Molecular Weight: 901.887

Synonyms:(3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2'-hydroxymethyl-5-thienylcarbonyl)methyl-azetidin-2-one

Chemical Property of (3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2'-hydroxymethyl-5-thienylcarbonyl)methyl-azetidin-2-one

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Technology Process of (3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2'-hydroxymethyl-5-thienylcarbonyl)methyl-azetidin-2-one

There total 7 articles about (3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2'-hydroxymethyl-5-thienylcarbonyl)methyl-azetidin-2-one 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: 71.0%

(3S*,4R*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2'-t-butyldimethylsilyloxymethyl-5'-thienylcarbonyl)methyl-azetidin-2-one (88139-94-0) → (3S*,4R*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2'-hydroxymethyl-5-thienylcarbonyl)methyl-azetidin-2-one (88139-99-5)

Guidance literature:

With hydrogenchloride; In tetrahydrofuran; methanol; for 2.5h; Ambient temperature;

DOI:10.1016/S0040-4020(01)92147-7

Reference yield:

5-bromothiophene-2-carboxylic acid (7311-63-9) → (3S*,4R*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2'-hydroxymethyl-5-thienylcarbonyl)methyl-azetidin-2-one (88139-99-5)

Guidance literature:

Multi-step reaction with 4 steps

1: diborane / tetrahydrofuran / 0 deg C, 15 min, RT, overnight

2: 53 percent / imidazole / dimethylformamide / Ambient temperature

4: 71 percent / conc HCl / methanol; tetrahydrofuran / 2.5 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; diborane; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)92147-7

Reference yield:

2-bromo-5-thiophene (88139-90-6) → (3S*,4R*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2'-hydroxymethyl-5-thienylcarbonyl)methyl-azetidin-2-one (88139-99-5)

Guidance literature:

Multi-step reaction with 2 steps

2: 71 percent / conc HCl / methanol; tetrahydrofuran / 2.5 h / Ambient temperature

With hydrogenchloride; In tetrahydrofuran; methanol;

DOI:10.1016/S0040-4020(01)92147-7

upstream raw materials:

(3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(2'-t-butyldimethylsilyloxymethyl-5'-thienylcarbonyl)methyl-azetidin-2-one

5-bromothiophene-2-carboxylic acid

2-bromo-5-thiophene

(5-bromothien-2-yl)methanol

Downstream raw materials:

o-nitrobenzyl-(5R^*,6S^*)-2-(2'-hydroxymethyl-5'-thienyl)-6-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-1-carbapen-2-em-3-carboxylate

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