(S)-2-{(R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-6-benzyloxy-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-benzenesulfonyl-ethyl ester

Base Information

• Chemical Name: (S)-2-{(R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-6-benzyloxy-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-benzenesulfonyl-ethyl ester
• CAS No.: 367276-21-9
• Molecular Formula: C₄₅H₅₉N₃O₂₀S
• Molecular Weight: 994.038
• Mol file: 367276-21-9.mol

Synonyms:(S)-2-{(R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-6-benzyloxy-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-benzenesulfonyl-ethyl ester

Chemical Property of (S)-2-{(R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-6-benzyloxy-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-benzenesulfonyl-ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-2-{(R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-6-benzyloxy-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-benzenesulfonyl-ethyl ester

There total 12 articles about (S)-2-{(R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-6-benzyloxy-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-benzenesulfonyl-ethyl 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: 67.0%

acetic anhydride (108-24-7) + 2-(2-{3-acetylamino-2-benzyloxy-6-benzyloxymethyl-5-[4,5-diacetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-4-yloxy}-propionylamino)-propionic acid 2-benzenesulfonyl-ethyl ester (367276-20-8) → (S)-2-{(R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-6-benzyloxy-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-benzenesulfonyl-ethyl ester (367276-21-9)

Guidance literature:

acetic anhydride; 2-(2-{3-acetylamino-2-benzyloxy-6-benzyloxymethyl-5-[4,5-diacetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-4-yloxy}-propionylamino)-propionic acid 2-benzenesulfonyl-ethyl ester; With zinc(II) chloride; In tetrahydrofuran; acetic acid; at 25 ℃; for 24h;

With zinc; at 25 ℃; for 4h; Further stages.;

DOI:10.1021/ol016692t

Reference yield:

3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide (67124-60-1) → (S)-2-{(R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-6-benzyloxy-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-benzenesulfonyl-ethyl ester (367276-21-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 84 percent / AgOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 20 °C

2.1: ZnCl₂ / acetic acid; tetrahydrofuran / 24 h / 25 °C

2.2: 67 percent / Zn / 4 h / 25 °C

With 4 A molecular sieve; silver trifluoromethanesulfonate; zinc(II) chloride; In tetrahydrofuran; dichloromethane; acetic acid;

DOI:10.1021/ol016692t

Reference yield:

benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside (73089-68-6) → (S)-2-{(R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-6-benzyloxy-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-benzenesulfonyl-ethyl ester (367276-21-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: N-methylmorpholine; 2-chloro-4,6-dimethoxy-1,3,5-triazine / CH₂Cl₂ / 0.75 h / 0 °C

1.2: 95 percent / N-methylmorpholine / CH₂Cl₂ / 72 h / 20 °C

2.1: 61 percent / Et₃SiH; TFA / CH₂Cl₂ / 0 °C

3.1: 84 percent / AgOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / 20 °C

4.1: ZnCl₂ / acetic acid; tetrahydrofuran / 24 h / 25 °C

4.2: 67 percent / Zn / 4 h / 25 °C

With 4-methyl-morpholine; triethylsilane; 2-chloro-4,6-dimethoxy-1 ,3,5-triazine; 4 A molecular sieve; silver trifluoromethanesulfonate; trifluoroacetic acid; zinc(II) chloride; In tetrahydrofuran; dichloromethane; acetic acid;

DOI:10.1021/ol016692t

upstream raw materials:

acetic anhydride

2-(2-{3-acetylamino-2-benzyloxy-6-benzyloxymethyl-5-[4,5-diacetoxy-6-acetoxymethyl-3-(2,2,2-trichloro-ethoxycarbonylamino)-tetrahydro-pyran-2-yloxy]-tetrahydro-pyran-4-yloxy}-propionylamino)-propionic acid 2-benzenesulfonyl-ethyl ester

3,4,6-Tri-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranosyl bromide

benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside

Downstream raw materials:

2-{2-[2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-benzenesulfonyl-ethyl ester

2-{2-[2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-(4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2,5-dioxo-pyrrolidin-1-yl ester

(S)-2-{(R)-2-[(2R,3S,4R,5R,6R)-2-Acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid

(S)-2-{(R)-2-[(2R,3S,4R,5R,6S)-2-Acetoxymethyl-5-acetylamino-3-((2S,3R,4R,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-3-acetylamino-tetrahydro-pyran-2-yloxy)-6-hydroxy-tetrahydro-pyran-4-yloxy]-propionylamino}-propionic acid 2-benzenesulfonyl-ethyl ester