Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-((2S,3R,4R,5R,6R)-3-acetylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-5-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-4-yl ester

Base Information

• Chemical Name: Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-((2S,3R,4R,5R,6R)-3-acetylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-5-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-4-yl ester
• CAS No.: 276241-29-3
• Molecular Formula: C₂₉H₃₉N₃O₁₇
• Molecular Weight: 701.639
• Mol file: 276241-29-3.mol

Synonyms:Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-((2S,3R,4R,5R,6R)-3-acetylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-5-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-4-yl ester

Chemical Property of Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-((2S,3R,4R,5R,6R)-3-acetylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-5-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-4-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-((2S,3R,4R,5R,6R)-3-acetylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-5-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-4-yl ester

There total 7 articles about Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-((2S,3R,4R,5R,6R)-3-acetylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-5-(4-nitro-benzyloxycarbonylamino)-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: 92.0%

Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-[(4aR,6S,7R,8R,8aR)-7-acetylamino-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-5-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-4-yl ester (276241-25-9) → Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-((2S,3R,4R,5R,6R)-3-acetylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-5-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-4-yl ester (276241-29-3)

Guidance literature:

With acetic acid; at 40 ℃; for 2h;

DOI:10.1016/S0960-894X(00)00107-4

Reference yield:

D-galactosamine (90-76-6,90-77-7,530-23-4,579-32-8,579-33-9,643-68-5,2596-19-2,6490-68-2,6490-70-6,6490-72-8,6490-73-9,6490-74-0,14196-84-0,14196-86-2,14257-69-3,58381-21-8) → Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-((2S,3R,4R,5R,6R)-3-acetylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-5-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-4-yl ester (276241-29-3)

Guidance literature:

Multi-step reaction with 6 steps

1: Et₃N / 0 °C

2: 95 percent / pyridine; DMAP

3: 87 percent / hydrazine acetate / dimethylformamide / 2 h / 0 °C

4: 90 percent / DBU / CH₂Cl₂ / -10 °C

5: 89 percent / Et₃SiOTf; mol. siev. 4 A / CH₂Cl₂ / 0.25 h / 20 °C

6: 92 percent / 80 percent aq. AcOH / 2 h / 40 °C

With pyridine; dmap; mol. siev. 4 A; triethylsilyl trifluoromethyl sulfonate; hydrazinium monoacetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; N,N-dimethyl-formamide; 1: Acylation / 2: Acetylation / 3: Deacetylation / 4: Addition / 5: glycosylation / 6: Hydrolysis;

DOI:10.1016/S0960-894X(00)00107-4

Reference yield:

((3R,4R,5R,6R)-2,4,5-Trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-carbamic acid 4-nitro-benzyl ester → Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-((2S,3R,4R,5R,6R)-3-acetylamino-5-hydroxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-5-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-4-yl ester (276241-29-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 95 percent / pyridine; DMAP

2: 87 percent / hydrazine acetate / dimethylformamide / 2 h / 0 °C

3: 90 percent / DBU / CH₂Cl₂ / -10 °C

4: 89 percent / Et₃SiOTf; mol. siev. 4 A / CH₂Cl₂ / 0.25 h / 20 °C

5: 92 percent / 80 percent aq. AcOH / 2 h / 40 °C

With pyridine; dmap; mol. siev. 4 A; triethylsilyl trifluoromethyl sulfonate; hydrazinium monoacetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; N,N-dimethyl-formamide; 1: Acetylation / 2: Deacetylation / 3: Addition / 4: glycosylation / 5: Hydrolysis;

DOI:10.1016/S0960-894X(00)00107-4

upstream raw materials:

Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-6-[(4aR,6S,7R,8R,8aR)-7-acetylamino-6-methoxy-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-5-(4-nitro-benzyloxycarbonylamino)-tetrahydro-pyran-4-yl ester

D-galactosamine

2-N-p-nitrobenzyloxycarbonyl-1,3,4,6-tetra-O-acetyl-D-galactosamine

Acetic acid (2R,3R,4R,5R,6R)-3-acetoxy-2-acetoxymethyl-5-(4-nitro-benzyloxycarbonylamino)-6-(2,2,2-trichloro-acetimidoyloxy)-tetrahydro-pyran-4-yl ester