(1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(benzyloxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate

Base Information

• Chemical Name: (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(benzyloxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate
• CAS No.: 113757-76-9
• Molecular Formula: C₂₈H₃₅NO₁₄
• Molecular Weight: 609.584
• Mol file: 113757-76-9.mol

Synonyms:(1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(benzyloxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate

Chemical Property of (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(benzyloxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(benzyloxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate

There total 6 articles about (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(benzyloxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate 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: 87.0%

acetic anhydride (108-24-7) + (2S,4S,5R,6R)-benzyl 5-acetamido-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-1-carboxylate (113757-75-8) → (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(benzyloxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate (113757-76-9)

Guidance literature:

With dmap; In pyridine; at 20 ℃; for 24h; Cooling with ice;

DOI:10.1021/jm3009713

Reference yield:

benzyl bromide (100-39-0) + (2R,4S,5R,6R)-2,4-Diacetoxy-5-acetylamino-6-((1R,2S)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid (108740-44-9) → 5-acetamido-2,4,7,8,9-penta-O-acetyl-3,5-dideoxy-D-glycero-β-D-galacto-2-nonulosonic acid benzyl ester (113757-76-9,126151-67-5,126253-07-4)

Guidance literature:

With potassium fluoride; In N,N-dimethyl-formamide; for 18h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4039(97)00138-X

Reference yield:

(4S,5R,6R)-5-Acetylamino-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester + acetic anhydride (108-24-7) → (1S,2R)-1-((2R,3R,4S,6R)-3-acetamido-4,6-diacetoxy-6-(benzyloxycarbonyl)tetrahydro-2H-pyran-2-yl)propane-1,2,3-triyl triacetate (113757-76-9) + (2S,4S,5R,6R)-2,4-Diacetoxy-5-acetylamino-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester (126151-67-5)

Guidance literature:

With pyridine; dmap; at 20 ℃; Overall yield = 7.39 g;

DOI:10.1039/d0ob01749c

upstream raw materials:

2,4,7,8,9-Penta-O-acetyl-N-acetyl-β-D-neuraminsaeure

benzyl bromide

acetic anhydride

(2S,4S,5R,6R)-benzyl 5-acetamido-2,4-dihydroxy-6-((1R,2R)-1,2,3-trihydroxypropyl)tetrahydro-2H-pyran-1-carboxylate

Downstream raw materials:

benzyl (5-acetamido-4,7,8,9-tetra-O-acetyl-2-chloro-3,5-dideoxy-D-glycero-α-D-galacto-non-2-ulpyranosid)onate

C₁₉H₂₆N₂O₈

C₂₇H₃₄N₂O₁₂

C₂₆H₃₂N₂O₁₁