Hexadecanoic acid 1-hexadecanoyloxymethyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl ester

Base Information

• Chemical Name: Hexadecanoic acid 1-hexadecanoyloxymethyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl ester
• CAS No.: 190505-17-0
• Molecular Formula: C₇₀H₁₀₄O₉
• Molecular Weight: 1089.59
• Mol file: 190505-17-0.mol

Synonyms:Hexadecanoic acid 1-hexadecanoyloxymethyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl ester

Chemical Property of Hexadecanoic acid 1-hexadecanoyloxymethyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Hexadecanoic acid 1-hexadecanoyloxymethyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl ester

There total 4 articles about Hexadecanoic acid 1-hexadecanoyloxymethyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl 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: 96.0%

1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-3,4-butandiol (190505-16-9) + n-hexadecanoyl chloride (112-67-4) → Hexadecanoic acid 1-hexadecanoyloxymethyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl ester (190505-17-0)

Guidance literature:

With dmap; In pyridine; at 100 ℃; for 3h;

DOI:10.1016/S0040-4020(97)00273-1

Reference yield:

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one (13096-62-3) → Hexadecanoic acid 1-hexadecanoyloxymethyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl ester (190505-17-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 88 percent / diethyl ether / 2 h / -78 °C

2: 97 percent / Et₃SiH, BF₃*OEt₂ / acetonitrile / 0.17 h / -18 °C

3: 1.) N-methylmorpholine-N-oxide, OsO₄, 2.) Na₂S₂O₃*5H₂O / 1.) acetone, H₂O, 3 h, 2.) acetone, H₂O, ethyl acetate, 2 h

4: 96 percent / dimethylaminopyridine / pyridine / 3 h / 100 °C

With triethylsilane; dmap; osmium(VIII) oxide; boron trifluoride diethyl etherate; sodium thiosulfate; 4-methylmorpholine N-oxide; In pyridine; diethyl ether; acetonitrile;

DOI:10.1016/S0040-4020(97)00273-1

Reference yield:

1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-3-butene (190505-15-8) → Hexadecanoic acid 1-hexadecanoyloxymethyl-3-((2S,3S,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-propyl ester (190505-17-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) N-methylmorpholine-N-oxide, OsO₄, 2.) Na₂S₂O₃*5H₂O / 1.) acetone, H₂O, 3 h, 2.) acetone, H₂O, ethyl acetate, 2 h

2: 96 percent / dimethylaminopyridine / pyridine / 3 h / 100 °C

With dmap; osmium(VIII) oxide; sodium thiosulfate; 4-methylmorpholine N-oxide; In pyridine;

DOI:10.1016/S0040-4020(97)00273-1

upstream raw materials:

1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-3,4-butandiol

n-hexadecanoyl chloride

(3R,4S,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-one

1-(2',3',4',6'-tetra-O-benzyl-β-D-glucopyranosyl)-3-butene