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

Base Information

• Chemical Name: (2R,3S,4R,5R,6R)-2-(acetoxymethyl)-6-phenoxy-5-((2,2,2-trichloroethoxy)carbonylamino)tetrahydro-2H-pyran-3,4-diyl diacetate
• CAS No.: 669763-26-2
• Molecular Formula: C₂₁H₂₄Cl₃NO₁₀
• Molecular Weight: 556.781
• Mol file: 669763-26-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about (2R,3S,4R,5R,6R)-2-(acetoxymethyl)-6-phenoxy-5-((2,2,2-trichloroethoxy)carbonylamino)tetrahydro-2H-pyran-3,4-diyl diacetate 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: 89.0%

1,3,4,6-tetra-O-acetyl-2-deoxy-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranose (122210-05-3) + phenol (108-95-2,27073-41-2) → (2R,3S,4R,5R,6R)-2-(acetoxymethyl)-6-phenoxy-5-((2,2,2-trichloroethoxy)carbonylamino)tetrahydro-2H-pyran-3,4-diyl diacetate (669763-26-2)

Guidance literature:

With tin(IV) chloride; In dichloromethane;

DOI:10.1055/s-2004-822902

Reference yield:

(2R,3S,4R,5R,6R)-2-(acetoxymethyl)-6-phenoxy-5-((2,2,2-trichloroethoxy)carbonylamino)tetrahydro-2H-pyran-3,4-diyl diacetate (669763-26-2) → Acetic acid (2R,3S,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-amino-6-phenoxy-tetrahydro-pyran-4-yl ester

Guidance literature:

With acetic acid; zinc; In tetrahydrofuran;

DOI:10.1055/s-2004-822902

Reference yield:

(2R,3S,4R,5R,6R)-2-(acetoxymethyl)-6-phenoxy-5-((2,2,2-trichloroethoxy)carbonylamino)tetrahydro-2H-pyran-3,4-diyl diacetate (669763-26-2) → 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 (884525-76-2)

Guidance literature:

Multi-step reaction with 10 steps

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

2.1: 1.13 g / aq. NaHCO₃ / CH₂Cl₂ / 1 h / 20 °C

3.1: Et₃N; MeOH / 12 h / 20 °C

4.1: pyridine / 1.5 h / 20 °C

5.1: 120 mg / pyridine / 1.5 h / 20 °C

6.1: 89 percent / NaN₃ / dimethylformamide / 2 h / 80 °C

7.1: 99 percent / Et₃N; MeOH / 2 h / 50 °C

8.1: PPh₃; H₂O / 2-methyl-propan-2-ol / 4 h / 60 °C

9.1: H₂O; methanol / 24 h / 20 °C

9.2: Et₃N / H₂O; methanol / 6 h

10.1: H₂ / Pd/C / H₂O / 24 h / 20 °C

With pyridine; methanol; sodium azide; water; hydrogen; sodium hydrogencarbonate; acetic acid; triethylamine; triphenylphosphine; zinc; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 8.1: Staudinger reaction;

DOI:10.1021/ja056253f

upstream raw materials:

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-2-acetoxymethyl-5-benzyloxycarbonylamino-6-phenoxy-tetrahydro-pyran-4-yl ester

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