Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-benzyloxycarbonylamino-6-phenoxy-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-benzyloxycarbonylamino-6-phenoxy-tetrahydro-pyran-4-yl ester
• CAS No.: 725740-17-0
• Molecular Formula: C₂₆H₂₉NO₁₀
• Molecular Weight: 515.517
• Mol file: 725740-17-0.mol

Synonyms:Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-benzyloxycarbonylamino-6-phenoxy-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-benzyloxycarbonylamino-6-phenoxy-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-benzyloxycarbonylamino-6-phenoxy-tetrahydro-pyran-4-yl ester

There total 6 articles about Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-benzyloxycarbonylamino-6-phenoxy-tetrahydro-pyran-4-yl 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:

benzyl chloroformate (501-53-1,94274-21-2) + Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-amino-6-phenoxy-tetrahydro-pyran-4-yl ester → Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-benzyloxycarbonylamino-6-phenoxy-tetrahydro-pyran-4-yl ester (725740-17-0)

Guidance literature:

With sodium hydrogencarbonate; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/ja056253f

Reference yield:

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose (122210-05-3) → Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-benzyloxycarbonylamino-6-phenoxy-tetrahydro-pyran-4-yl ester (725740-17-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / SnCl₄ / CH₂Cl₂ / 48 h / 20 °C

2: Zn; AcOH / tetrahydrofuran / 1.5 h / 20 °C

3: 1.13 g / aq. NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

With tin(IV) chloride; sodium hydrogencarbonate; acetic acid; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja056253f

Reference yield:

phenol (108-95-2,27073-41-2) → Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-benzyloxycarbonylamino-6-phenoxy-tetrahydro-pyran-4-yl ester (725740-17-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 89 percent / SnCl₄ / CH₂Cl₂ / 48 h / 20 °C

2: Zn; AcOH / tetrahydrofuran / 1.5 h / 20 °C

3: 1.13 g / aq. NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

With tin(IV) chloride; sodium hydrogencarbonate; acetic acid; zinc; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja056253f

upstream raw materials:

benzyl chloroformate

(2R,3S,4R,5R,6R)-2-(acetoxymethyl)-6-phenoxy-5-((2,2,2-trichloroethoxy)carbonylamino)tetrahydro-2H-pyran-3,4-diyl diacetate

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose

phenol

Downstream raw materials:

Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-5-benzyloxycarbonylamino-6-phenoxy-2-(toluene-4-sulfonyloxymethyl)-tetrahydro-pyran-4-yl ester

1-((2R,3S,4R,5R,6R)-5-Amino-3,4-dihydroxy-6-phenoxy-tetrahydro-pyran-2-ylmethyl)-3-[(2R,3R,4R,5S,6R)-3,4-dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-urea

(6-{3-[3,4-dihydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yl]-ureidomethyl}-4,5-dihydroxy-2-phenoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester

((2R,3R,4R,5S,6R)-6-Aminomethyl-4,5-dihydroxy-2-phenoxy-tetrahydro-pyran-3-yl)-carbamic acid benzyl ester