(2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-((S)-2-benzyloxy-3-octanoyloxy-propoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Base Information

• Chemical Name: (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-((S)-2-benzyloxy-3-octanoyloxy-propoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester
• CAS No.: 126568-94-3
• Molecular Formula: C₃₈H₅₅NO₁₆
• Molecular Weight: 781.852
• Mol file: 126568-94-3.mol

Synonyms:

Chemical Property of (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-((S)-2-benzyloxy-3-octanoyloxy-propoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-((S)-2-benzyloxy-3-octanoyloxy-propoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester

There total 4 articles about (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-((S)-2-benzyloxy-3-octanoyloxy-propoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl 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: 15.6%

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester (67670-69-3) + Octanoic acid (S)-2-benzyloxy-3-hydroxy-propyl ester (126568-86-3) → (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-((S)-2-benzyloxy-3-octanoyloxy-propoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (126568-94-3) + (2R,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-((S)-2-benzyloxy-3-octanoyloxy-propoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (126568-90-9)

Guidance literature:

With 4 A molecular sieve; mercury(II) cyanide; mercury dibromide; In dichloromethane; for 96h; Ambient temperature;

DOI:10.1248/cpb.38.3347

Reference yield:

(S)-2-(benzyloxy)-3-hydroxypropyl acetate (109429-01-8) → (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-((S)-2-benzyloxy-3-octanoyloxy-propoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (126568-94-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 72.5 percent / pyridine / 3 h / 80 °C

2: 77.4 percent / NH₄OH / methanol / 15 h / Ambient temperature

3: 88.8 percent / triethylamine / CH₂Cl₂ / 15 h / Ambient temperature

4: 85.8 percent / 80percent AcOH / 1 h / 80 °C

5: 17.1 percent / Hg(CN)2, HgBr₂, molecular sieves 4A / CH₂Cl₂ / 96 h / Ambient temperature

With pyridine; ammonium hydroxide; 4 A molecular sieve; mercury(II) cyanide; acetic acid; triethylamine; mercury dibromide; In methanol; dichloromethane;

DOI:10.1248/cpb.38.3347

Reference yield:

(R)-2-benzyloxy-3-trityloxy-propan-1-ol (91274-04-3) → (2S,4S,5R,6R)-4-Acetoxy-5-acetylamino-2-((S)-2-benzyloxy-3-octanoyloxy-propoxy)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid methyl ester (126568-94-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 88.8 percent / triethylamine / CH₂Cl₂ / 15 h / Ambient temperature

2: 85.8 percent / 80percent AcOH / 1 h / 80 °C

3: 17.1 percent / Hg(CN)2, HgBr₂, molecular sieves 4A / CH₂Cl₂ / 96 h / Ambient temperature

With 4 A molecular sieve; mercury(II) cyanide; acetic acid; triethylamine; mercury dibromide; In dichloromethane;

DOI:10.1248/cpb.38.3347

upstream raw materials:

N-acetyl-4,7,8,9-tetra-O-acetyl-2-chloro-2-deoxyneuraminic acid methyl ester

Octanoic acid (S)-2-benzyloxy-3-hydroxy-propyl ester

(S)-2-(benzyloxy)-3-hydroxypropyl acetate

(R)-2-benzyloxy-3-trityloxy-propan-1-ol