(S)-3-[(2S,3R,4R,5R,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-benzyloxycarbonylamino-propionic acid benzyl ester

Base Information

• Chemical Name: (S)-3-[(2S,3R,4R,5R,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-benzyloxycarbonylamino-propionic acid benzyl ester
• CAS No.: 1054736-14-9
• Molecular Formula: C₄₀H₅₀N₂O₁₉
• Molecular Weight: 862.839
• Mol file: 1054736-14-9.mol

Synonyms:

Chemical Property of (S)-3-[(2S,3R,4R,5R,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-benzyloxycarbonylamino-propionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-[(2S,3R,4R,5R,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-benzyloxycarbonylamino-propionic acid benzyl ester

There total 5 articles about (S)-3-[(2S,3R,4R,5R,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-benzyloxycarbonylamino-propionic acid 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:

(S)-3-[(4aR,6S,7R,8R,8aR)-7-Acetylamino-2,2-di-tert-butyl-8-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-1,3,5-trioxa-2-sila-naphthalen-6-yloxy]-2-benzyloxycarbonylamino-propionic acid benzyl ester (335105-71-0) → (S)-3-[(2S,3R,4R,5R,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-benzyloxycarbonylamino-propionic acid benzyl ester (1054736-14-9)

Guidance literature:

With triethylamine tris(hydrogen fluoride); In tetrahydrofuran; at 0 - 25 ℃; for 4h;

DOI:10.1016/S0040-4039(01)00044-2

Reference yield:

2-azido-2-deoxy-β-D-galactopyranosyl fluoride (335105-68-5) → (S)-3-[(2S,3R,4R,5R,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-benzyloxycarbonylamino-propionic acid benzyl ester (1054736-14-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / 1-hydroxybenzotriazole; pyridine / 95 °C

2: 85 percent / TMSOTf / CH₂Cl₂ / 3 h / -20 °C

3: 73 percent / Cp₂ZrCl₂; AgClO₄ / CH₂Cl₂ / 2 h / 25 °C

4: 80 percent / pyridine / 16 h

5: Et₃N-3HF / tetrahydrofuran / 4 h / 0 - 25 °C

With pyridine; zirconocene dichloride; trimethylsilyl trifluoromethanesulfonate; silver perchlorate; benzotriazol-1-ol; triethylamine tris(hydrogen fluoride); In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(01)00044-2

Reference yield:

(4aR,6S,7R,8R,8aR)-7-Azido-2,2-di-tert-butyl-6-fluoro-hexahydro-1,3,5-trioxa-2-sila-naphthalen-8-ol (259236-39-0) → (S)-3-[(2S,3R,4R,5R,6R)-3-Acetylamino-5-hydroxy-6-hydroxymethyl-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-2-benzyloxycarbonylamino-propionic acid benzyl ester (1054736-14-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 85 percent / TMSOTf / CH₂Cl₂ / 3 h / -20 °C

2: 73 percent / Cp₂ZrCl₂; AgClO₄ / CH₂Cl₂ / 2 h / 25 °C

3: 80 percent / pyridine / 16 h

4: Et₃N-3HF / tetrahydrofuran / 4 h / 0 - 25 °C

With pyridine; zirconocene dichloride; trimethylsilyl trifluoromethanesulfonate; silver perchlorate; triethylamine tris(hydrogen fluoride); In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(01)00044-2

upstream raw materials:

(S)-3-[(4aR,6S,7R,8R,8aR)-7-Acetylamino-2,2-di-tert-butyl-8-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-hexahydro-1,3,5-trioxa-2-sila-naphthalen-6-yloxy]-2-benzyloxycarbonylamino-propionic acid benzyl ester

2-azido-2-deoxy-β-D-galactopyranosyl fluoride

(4aR,6S,7R,8R,8aR)-7-Azido-2,2-di-tert-butyl-6-fluoro-hexahydro-1,3,5-trioxa-2-sila-naphthalen-8-ol

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-((4aR,6S,7R,8R,8aR)-7-azido-2,2-di-tert-butyl-6-fluoro-hexahydro-1,3,5-trioxa-2-sila-naphthalen-8-yloxy)-tetrahydro-pyran-3-yl ester

Downstream raw materials:

3-O-(2-acetamido-2-deoxy-3-O-β-D-galactopyranosyl-α-D-galactopyranosyl)-L-serine

N-(benzyloxycarbonyl)-[2-acetamido-2-deoxy-3-O-(β-D-galactopyranosyl)-(1->3)-α-D-galactopyranosyl]-L-serine