(3S,S_P)-1-amino(sulfoamino)-phosphinyl-3-benzyloxycarbonylamino-2-piperidinone (1S,2R)-(+)-2-amino-1,2-diphenylethanol salt

Base Information

• Chemical Name: (3S,S_P)-1-amino(sulfoamino)-phosphinyl-3-benzyloxycarbonylamino-2-piperidinone (1S,2R)-(+)-2-amino-1,2-diphenylethanol salt
• CAS No.: 548491-37-8
• Molecular Formula: C₁₃H₁₉N₄O₇PS*C₁₄H₁₅NO
• Molecular Weight: 619.635

Synonyms:(3S,S_P)-1-amino(sulfoamino)-phosphinyl-3-benzyloxycarbonylamino-2-piperidinone (1S,2R)-(+)-2-amino-1,2-diphenylethanol salt

Chemical Property of (3S,S_P)-1-amino(sulfoamino)-phosphinyl-3-benzyloxycarbonylamino-2-piperidinone (1S,2R)-(+)-2-amino-1,2-diphenylethanol salt

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Technology Process of (3S,S_P)-1-amino(sulfoamino)-phosphinyl-3-benzyloxycarbonylamino-2-piperidinone (1S,2R)-(+)-2-amino-1,2-diphenylethanol salt

There total 5 articles about (3S,S_P)-1-amino(sulfoamino)-phosphinyl-3-benzyloxycarbonylamino-2-piperidinone (1S,2R)-(+)-2-amino-1,2-diphenylethanol salt 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: 42.0%

(1S,2R)-2-Amino-1,2-diphenylethanol (23364-44-5) + (3S,RSP)-1-amino(sulfoamino)phosphinyl-3-benzyloxycarbonylamino-2-piperidinone sodium salt → (3S,SP)-1-amino(sulfoamino)-phosphinyl-3-benzyloxycarbonylamino-2-piperidinone (1S,2R)-(+)-2-amino-1,2-diphenylethanol salt (548491-37-8) + C13H19N4O7PS*C14H15NO

Guidance literature:

With hydrogenchloride; In water; at 90 ℃;

DOI:10.1021/op058000c

Reference yield:

L-ornithine hydrochloride (3184-13-2,36630-89-4) → (3S,SP)-1-amino(sulfoamino)-phosphinyl-3-benzyloxycarbonylamino-2-piperidinone (1S,2R)-(+)-2-amino-1,2-diphenylethanol salt (548491-37-8) + C13H19N4O7PS*C14H15NO

Guidance literature:

Multi-step reaction with 6 steps

1.1: thionyl chloride / 3 h / 0 - 55 °C / Large scale

2.1: sodium carbonate / water / 12 h / 5 - 20 °C / Large scale

3.1: sodium hydrogencarbonate / water; tetrahydrofuran / 1 h / 10 - 20 °C / Large scale

4.1: chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 24 h / 20 °C

4.2: 48 h / 20 °C

4.3: Cooling with ice

5.1: sulfur trioxide pyridine complex / N,N-dimethyl-formamide / 12 h / 0 - 8 °C

5.2: 0.08 h / 20 °C

6.1: hydrogenchloride / water / 90 °C

With hydrogenchloride; chloro-trimethyl-silane; thionyl chloride; sulfur trioxide pyridine complex; sodium hydrogencarbonate; sodium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1021/op058000c

Reference yield:

methyl (S)-2,5-diaminopentanoate dihydrochloride (40216-82-8,60080-69-5) → (3S,SP)-1-amino(sulfoamino)-phosphinyl-3-benzyloxycarbonylamino-2-piperidinone (1S,2R)-(+)-2-amino-1,2-diphenylethanol salt (548491-37-8) + C13H19N4O7PS*C14H15NO

Guidance literature:

Multi-step reaction with 5 steps

1.1: sodium carbonate / water / 12 h / 5 - 20 °C / Large scale

2.1: sodium hydrogencarbonate / water; tetrahydrofuran / 1 h / 10 - 20 °C / Large scale

3.1: chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 24 h / 20 °C

3.2: 48 h / 20 °C

3.3: Cooling with ice

4.1: sulfur trioxide pyridine complex / N,N-dimethyl-formamide / 12 h / 0 - 8 °C

4.2: 0.08 h / 20 °C

5.1: hydrogenchloride / water / 90 °C

With hydrogenchloride; chloro-trimethyl-silane; sulfur trioxide pyridine complex; sodium hydrogencarbonate; sodium carbonate; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1021/op058000c

upstream raw materials:

L-ornithine hydrochloride

methyl (S)-2,5-diaminopentanoate dihydrochloride

(3S)-3-benzyloxycarbonylamino-1-diaminophosphinyl-2-piperidinone

(1S,2R)-2-Amino-1,2-diphenylethanol

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