Benzyloxycarbonylamino-thioacetic acid S-(3-{(2R,3R)-3-[3-(2-benzyloxycarbonylamino-acetylsulfanyl)-phenylsulfanylmethyl]-1,4,7,10,13,16-hexaoxa-cyclooctadec-2-ylmethylsulfanyl}-phenyl) ester

Base Information

• Chemical Name: Benzyloxycarbonylamino-thioacetic acid S-(3-{(2R,3R)-3-[3-(2-benzyloxycarbonylamino-acetylsulfanyl)-phenylsulfanylmethyl]-1,4,7,10,13,16-hexaoxa-cyclooctadec-2-ylmethylsulfanyl}-phenyl) ester
• CAS No.: 125372-65-8
• Molecular Formula: C₄₆H₅₄N₂O₁₂S₄
• Molecular Weight: 955.205

Synonyms:

Chemical Property of Benzyloxycarbonylamino-thioacetic acid S-(3-{(2R,3R)-3-[3-(2-benzyloxycarbonylamino-acetylsulfanyl)-phenylsulfanylmethyl]-1,4,7,10,13,16-hexaoxa-cyclooctadec-2-ylmethylsulfanyl}-phenyl) ester

Chemical Property:

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Technology Process of Benzyloxycarbonylamino-thioacetic acid S-(3-{(2R,3R)-3-[3-(2-benzyloxycarbonylamino-acetylsulfanyl)-phenylsulfanylmethyl]-1,4,7,10,13,16-hexaoxa-cyclooctadec-2-ylmethylsulfanyl}-phenyl) ester

There total 3 articles about Benzyloxycarbonylamino-thioacetic acid S-(3-{(2R,3R)-3-[3-(2-benzyloxycarbonylamino-acetylsulfanyl)-phenylsulfanylmethyl]-1,4,7,10,13,16-hexaoxa-cyclooctadec-2-ylmethylsulfanyl}-phenyl) ester 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:

3-mercaptothiophenol (626-04-0) → Benzyloxycarbonylamino-thioacetic acid S-(3-{(2R,3R)-3-[3-(2-benzyloxycarbonylamino-acetylsulfanyl)-phenylsulfanylmethyl]-1,4,7,10,13,16-hexaoxa-cyclooctadec-2-ylmethylsulfanyl}-phenyl) ester (125372-65-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 27 percent / 1N aq. KOH / ethanol; tetrahydrofuran / 2 h / 50 °C

2: 1.) Et₃N, 2.) pyridine / 1.) EtOH, room t., 30 min, 2.) acetone, room t., 15 min

With pyridine; potassium hydroxide; triethylamine; In tetrahydrofuran; ethanol;

DOI:10.1248/cpb.37.912

Reference yield:

(1S,2S)-1,2-Bis-tosyloxymethyl-18-krone-6 (73893-12-6) → Benzyloxycarbonylamino-thioacetic acid S-(3-{(2R,3R)-3-[3-(2-benzyloxycarbonylamino-acetylsulfanyl)-phenylsulfanylmethyl]-1,4,7,10,13,16-hexaoxa-cyclooctadec-2-ylmethylsulfanyl}-phenyl) ester (125372-65-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 27 percent / 1N aq. KOH / ethanol; tetrahydrofuran / 2 h / 50 °C

2: 1.) Et₃N, 2.) pyridine / 1.) EtOH, room t., 30 min, 2.) acetone, room t., 15 min

With pyridine; potassium hydroxide; triethylamine; In tetrahydrofuran; ethanol;

DOI:10.1248/cpb.37.912

Reference yield:

Z-Gly-ONp (1738-86-9) + L-alanine p-nitrophenyl ester hydrobromide (5673-65-4) + (+)-(2S,3S)-2,3-bis(3-mercaptophenylthiomethyl)-1,4,7,10,13,16-hexaoxacyclooctadecane (125372-54-5) → Benzyloxycarbonylamino-thioacetic acid S-(3-{(2R,3R)-3-[3-(2-benzyloxycarbonylamino-acetylsulfanyl)-phenylsulfanylmethyl]-1,4,7,10,13,16-hexaoxa-cyclooctadec-2-ylmethylsulfanyl}-phenyl) ester (125372-65-8) + (2S,3S)-S-(N-carbobenzyloxyglycyl)-S'-L-alanyl-2,3-bis(3-mercaptophenylthiomethyl)-1,4,7,10,13,16-hexaoxacyclooctadecane

Guidance literature:

With pyridine; triethylamine; Yield given. Multistep reaction. Yields of byproduct given; 1.) EtOH, room t., 30 min, 2.) acetone, room t., 15 min;

DOI:10.1248/cpb.37.912

upstream raw materials:

Z-Gly-ONp

L-alanine p-nitrophenyl ester hydrobromide

(+)-(2S,3S)-2,3-bis(3-mercaptophenylthiomethyl)-1,4,7,10,13,16-hexaoxacyclooctadecane

3-mercaptothiophenol

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