(S)-t-butyl 4-(2-((2S,3R,4S,5S,6R)-2-benzamido-3,4,5-tris(benzyloxy)-6-benzyloxymethyltetrahydro-2H-pyran-2-yl)acetamido)-2-(t-butoxycarbonylamino)butanoate

Base Information

• Chemical Name: (S)-t-butyl 4-(2-((2S,3R,4S,5S,6R)-2-benzamido-3,4,5-tris(benzyloxy)-6-benzyloxymethyltetrahydro-2H-pyran-2-yl)acetamido)-2-(t-butoxycarbonylamino)butanoate
• CAS No.: 849472-56-6
• Molecular Formula: C₅₆H₆₇N₃O₁₁
• Molecular Weight: 958.161

Synonyms:(S)-t-butyl 4-(2-((2S,3R,4S,5S,6R)-2-benzamido-3,4,5-tris(benzyloxy)-6-benzyloxymethyltetrahydro-2H-pyran-2-yl)acetamido)-2-(t-butoxycarbonylamino)butanoate

Chemical Property of (S)-t-butyl 4-(2-((2S,3R,4S,5S,6R)-2-benzamido-3,4,5-tris(benzyloxy)-6-benzyloxymethyltetrahydro-2H-pyran-2-yl)acetamido)-2-(t-butoxycarbonylamino)butanoate

Chemical Property:

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Technology Process of (S)-t-butyl 4-(2-((2S,3R,4S,5S,6R)-2-benzamido-3,4,5-tris(benzyloxy)-6-benzyloxymethyltetrahydro-2H-pyran-2-yl)acetamido)-2-(t-butoxycarbonylamino)butanoate

There total 4 articles about (S)-t-butyl 4-(2-((2S,3R,4S,5S,6R)-2-benzamido-3,4,5-tris(benzyloxy)-6-benzyloxymethyltetrahydro-2H-pyran-2-yl)acetamido)-2-(t-butoxycarbonylamino)butanoate 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: 75.0%

(S)-4-amino-2-(tert-butoxycarbonylamino)butyric acid tert-butyl ester hydrochloride (250611-08-6) + benzonitrile (100-47-0) + ((3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic acid (381724-75-0) → (S)-t-butyl 4-(2-((2S,3R,4S,5S,6R)-2-benzamido-3,4,5-tris(benzyloxy)-6-benzyloxymethyltetrahydro-2H-pyran-2-yl)acetamido)-2-(t-butoxycarbonylamino)butanoate (849472-56-6)

Guidance literature:

benzonitrile; ((3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic acid; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at 0 ℃; for 2h;

(S)-4-amino-2-(tert-butoxycarbonylamino)butyric acid tert-butyl ester hydrochloride; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃; for 12h;

DOI:10.1055/s-2004-837204

Reference yield:

(S)-4-amino-2-(tert-butoxycarbonylamino)butyric acid tert-butyl ester hydrochloride (250611-08-6) + (6S,8R,9S,10S,11R)-9,10,11-Tris-benzyloxy-8-benzyloxymethyl-2-phenyl-3,7-dioxa-1-aza-spiro[5.5]undec-1-en-4-one (381724-76-1) → (S)-t-butyl 4-(2-((2S,3R,4S,5S,6R)-2-benzamido-3,4,5-tris(benzyloxy)-6-benzyloxymethyltetrahydro-2H-pyran-2-yl)acetamido)-2-(t-butoxycarbonylamino)butanoate (849472-56-6)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 12h;

DOI:10.1016/j.carres.2006.11.006

Reference yield:

2-deoxy-α-D-galacto-oct-3-ulopyranosonic acid → (S)-t-butyl 4-(2-((2S,3R,4S,5S,6R)-2-benzamido-3,4,5-tris(benzyloxy)-6-benzyloxymethyltetrahydro-2H-pyran-2-yl)acetamido)-2-(t-butoxycarbonylamino)butanoate (849472-56-6)

Guidance literature:

Multi-step reaction with 2 steps

1: TMSOTf / CH₂Cl₂ / 2 h / 0 °C

2: diisopropylethylamine / CH₂Cl₂ / 12 h / 0 °C

With trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; In dichloromethane;

DOI:10.1016/j.carres.2006.11.006

upstream raw materials:

(S)-4-amino-2-(tert-butoxycarbonylamino)butyric acid tert-butyl ester hydrochloride

benzonitrile

((3R,4S,5S,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-2-hydroxy-tetrahydro-pyran-2-yl)-acetic acid

(6S,8R,9S,10S,11R)-9,10,11-Tris-benzyloxy-8-benzyloxymethyl-2-phenyl-3,7-dioxa-1-aza-spiro[5.5]undec-1-en-4-one

Downstream raw materials:

(S)-4-(2-((2S,3R,4S,5R,6R)-2-benzamido-3,4,5-tris(acetoxy)-6-acetoxymethyltetrahydro-2H-pyran-2-yl)acetamido)-2-(9-fluorenylmethoxycarbonylamino)butanoic acid

(S)-2-tert-Butoxycarbonylamino-4-[2-((2S,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-2-benzoylamino-tetrahydro-pyran-2-yl)-acetylamino]-butyric acid tert-butyl ester

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