(R)-2-[(2S,3S)-2-((2S,3R)-2-tert-Butoxycarbonylamino-3-hydroxy-butyrylamino)-3-methyl-pentanoylamino]-3-hexadecanoylsulfanyl-propionic acid 4-phenylacetoxy-benzyl ester

Base Information

• Chemical Name: (R)-2-[(2S,3S)-2-((2S,3R)-2-tert-Butoxycarbonylamino-3-hydroxy-butyrylamino)-3-methyl-pentanoylamino]-3-hexadecanoylsulfanyl-propionic acid 4-phenylacetoxy-benzyl ester
• CAS No.: 330970-76-8
• Molecular Formula: C₄₉H₇₅N₃O₁₀S
• Molecular Weight: 898.215

Synonyms:(R)-2-[(2S,3S)-2-((2S,3R)-2-tert-Butoxycarbonylamino-3-hydroxy-butyrylamino)-3-methyl-pentanoylamino]-3-hexadecanoylsulfanyl-propionic acid 4-phenylacetoxy-benzyl ester

Chemical Property of (R)-2-[(2S,3S)-2-((2S,3R)-2-tert-Butoxycarbonylamino-3-hydroxy-butyrylamino)-3-methyl-pentanoylamino]-3-hexadecanoylsulfanyl-propionic acid 4-phenylacetoxy-benzyl ester

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Technology Process of (R)-2-[(2S,3S)-2-((2S,3R)-2-tert-Butoxycarbonylamino-3-hydroxy-butyrylamino)-3-methyl-pentanoylamino]-3-hexadecanoylsulfanyl-propionic acid 4-phenylacetoxy-benzyl ester

There total 5 articles about (R)-2-[(2S,3S)-2-((2S,3R)-2-tert-Butoxycarbonylamino-3-hydroxy-butyrylamino)-3-methyl-pentanoylamino]-3-hexadecanoylsulfanyl-propionic acid 4-phenylacetoxy-benzyl 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: 74.0%

Boc-Thr-OH (2592-18-9) + (R)-2-((2S,3S)-2-Amino-3-methyl-pentanoylamino)-3-hexadecanoylsulfanyl-propionic acid 4-phenylacetoxy-benzyl ester; compound with trifluoro-acetic acid → (R)-2-[(2S,3S)-2-((2S,3R)-2-tert-Butoxycarbonylamino-3-hydroxy-butyrylamino)-3-methyl-pentanoylamino]-3-hexadecanoylsulfanyl-propionic acid 4-phenylacetoxy-benzyl ester (330970-76-8)

Guidance literature:

With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; In dichloromethane; at 20 ℃; for 18h;

DOI:10.1002/1521-3765(20020802)8:15<3362::AID-CHEM3362>3.0.CO;2-0

Reference yield: 74.0%

Boc-Thr-OH (2592-18-9) + (R)-2-((2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-pentanoylamino)-3-hexadecanoylsulfanyl-propionic acid 4-phenylacetoxy-benzyl ester (330970-73-5) → (R)-2-[(2S,3S)-2-((2S,3R)-2-tert-Butoxycarbonylamino-3-hydroxy-butyrylamino)-3-methyl-pentanoylamino]-3-hexadecanoylsulfanyl-propionic acid 4-phenylacetoxy-benzyl ester (330970-76-8)

Guidance literature:

(R)-2-((2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-pentanoylamino)-3-hexadecanoylsulfanyl-propionic acid 4-phenylacetoxy-benzyl ester; With trifluoroacetic acid;

Boc-Thr-OH; With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine;

DOI:10.1002/1521-3773(20010119)40:2<369::AID-ANIE369>3.0.CO;2-7

Reference yield:

N-(tert-butyloxycarbonyl)-L-isoleucine (13139-16-7) → (R)-2-[(2S,3S)-2-((2S,3R)-2-tert-Butoxycarbonylamino-3-hydroxy-butyrylamino)-3-methyl-pentanoylamino]-3-hexadecanoylsulfanyl-propionic acid 4-phenylacetoxy-benzyl ester (330970-76-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: EEDQ

2.1: DTT; Et₃N

2.2: 83 percent / Et₃N

3.1: TFA

3.2: 74 percent / EEDQ; Et₃N

With DL-dithiothreitol; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; triethylamine; trifluoroacetic acid;

DOI:10.1002/1521-3773(20010119)40:2<369::AID-ANIE369>3.0.CO;2-7

upstream raw materials:

Boc-Thr-OH

(R)-2-((2S,3S)-2-tert-Butoxycarbonylamino-3-methyl-pentanoylamino)-3-hexadecanoylsulfanyl-propionic acid 4-phenylacetoxy-benzyl ester

N-(tert-butyloxycarbonyl)-L-isoleucine

(R)-2-Amino-3-[(R)-2-amino-2-(4-phenylacetoxy-benzyloxycarbonyl)-ethyldisulfanyl]-propionic acid 4-phenylacetoxy-benzyl ester

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