[(2S,3R,4R,5R,6R)-5-Acetoxy-6-acetoxymethyl-3-azido-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-acetic acid benzyl ester

Base Information

• Chemical Name: [(2S,3R,4R,5R,6R)-5-Acetoxy-6-acetoxymethyl-3-azido-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-acetic acid benzyl ester
• CAS No.: 183801-53-8
• Molecular Formula: C₃₃H₄₁N₃O₁₈
• Molecular Weight: 767.698

Synonyms:

Chemical Property of [(2S,3R,4R,5R,6R)-5-Acetoxy-6-acetoxymethyl-3-azido-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-acetic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2S,3R,4R,5R,6R)-5-Acetoxy-6-acetoxymethyl-3-azido-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-acetic acid benzyl ester

There total 5 articles about [(2S,3R,4R,5R,6R)-5-Acetoxy-6-acetoxymethyl-3-azido-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-acetic 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:

tert-butyldimethylsilyl 2-azido-2-deoxy-4,6-O-isopropylidene-β-D-galactopyranoside (114117-04-3) → [(2S,3R,4R,5R,6R)-5-Acetoxy-6-acetoxymethyl-3-azido-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-acetic acid benzyl ester (183801-53-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 71 percent / Ag₂CO₃, AgClO₄, 4 Angstroem molecular sieves / CH₂Cl₂ / 9 h / Ambient temperature

2: 86 percent / Bu₄NF / tetrahydrofuran / 3 h / -20 °C

3: 92 percent / Et₃N / CH₂Cl₂ / 24 h / Ambient temperature

4: 59 percent / AgOTf, 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

5: aq AcOH / 4 h / 60 °C

6: pyridine / Ambient temperature

With 4 A molecular sieve; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; silver perchlorate; acetic acid; triethylamine; silver carbonate; In tetrahydrofuran; pyridine; dichloromethane;

DOI:10.1139/v96-192

Reference yield:

2-azido-2-deoxy-3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-4,6-O-isopropylidene-D-galactopyranose → [(2S,3R,4R,5R,6R)-5-Acetoxy-6-acetoxymethyl-3-azido-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-acetic acid benzyl ester (183801-53-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 92 percent / Et₃N / CH₂Cl₂ / 24 h / Ambient temperature

2: 59 percent / AgOTf, 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

3: aq AcOH / 4 h / 60 °C

4: pyridine / Ambient temperature

With 4 A molecular sieve; silver trifluoromethanesulfonate; acetic acid; triethylamine; In pyridine; dichloromethane;

DOI:10.1139/v96-192

Reference yield:

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(4aR,6S,7R,8R,8aR)-7-azido-2,2-dimethyl-6-(pyridin-2-ylsulfanylcarbonyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-tetrahydro-pyran-3-yl ester (183801-47-0) → [(2S,3R,4R,5R,6R)-5-Acetoxy-6-acetoxymethyl-3-azido-4-((2R,3R,4S,5S,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-acetic acid benzyl ester (183801-53-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 59 percent / AgOTf, 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / Ambient temperature

2: aq AcOH / 4 h / 60 °C

3: pyridine / Ambient temperature

With 4 A molecular sieve; silver trifluoromethanesulfonate; acetic acid; In pyridine; dichloromethane;

DOI:10.1139/v96-192

upstream raw materials:

tert-butyldimethylsilyl 2-azido-2-deoxy-4,6-O-isopropylidene-β-D-galactopyranoside

Acetic acid (2R,3R,4S,5S,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(4aR,6S,7R,8R,8aR)-7-azido-2,2-dimethyl-6-(pyridin-2-ylsulfanylcarbonyloxy)-hexahydro-pyrano[3,2-d][1,3]dioxin-8-yloxy]-tetrahydro-pyran-3-yl ester

benzyloxycarbonylmethyl 3-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-2-deoxy-4,6-O-isopropylidene-α-D-galactopyranoside

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside

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