Hexadecanoic acid (S)-2-hydroxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester

Base Information

• Chemical Name: Hexadecanoic acid (S)-2-hydroxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester
• CAS No.: 158227-69-1
• Molecular Formula: C₄₆H₆₆O₉
• Molecular Weight: 763.025
• Mol file: 158227-69-1.mol

Synonyms:

Chemical Property of Hexadecanoic acid (S)-2-hydroxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Hexadecanoic acid (S)-2-hydroxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester

There total 4 articles about Hexadecanoic acid (S)-2-hydroxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-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: 70.0%

caesium palmitate (14912-92-6) + [(2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-6-((S)-1-oxiranylmethoxy)-tetrahydro-pyran-2-yl]-methanol → Hexadecanoic acid (S)-2-hydroxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester (158227-69-1)

Guidance literature:

In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)73526-X

Reference yield:

caesium palmitate (14912-92-6) + 6-O-acetyl-2,3,4,-tri-O-benzyl-α-D-glucopyranose (88567-49-1) + (S)-oxiranemethanol (60456-23-7) → Hexadecanoic acid (S)-2-hydroxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester (158227-69-1)

Guidance literature:

6-O-acetyl-2,3,4,-tri-O-benzyl-α-D-glucopyranose; With carbon tetrabromide; triphenylphosphine; In N,N-dimethyl-formamide; at 20 ℃; for 3h;

(S)-oxiranemethanol; In N,N-dimethyl-formamide; at 20 ℃; for 14h;

caesium palmitate; Further stages;

DOI:10.3762/bjoc.8.70

Reference yield:

2,3,4-tri-O-benzyl-6-O-p-nitrobenzoyl-α-D-glucopyranosyl bromide (39483-53-9) → Hexadecanoic acid (S)-2-hydroxy-3-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-propyl ester (158227-69-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / tetramethylurea / CH₂Cl₂

2: sodium methoxide / methanol

3: 70 percent / dimethylformamide

With sodium methylate; tetramethylurea; In methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)73526-X

upstream raw materials:

caesium palmitate

2,3,4-tri-O-benzyl-6-O-p-nitrobenzoyl-α-D-glucopyranosyl bromide

(2R,3R,4S,5R,6S)-3,4,5-Tris-benzyloxy-2-(4-nitro-benzyloxymethyl)-6-((S)-1-oxiranylmethoxy)-tetrahydro-pyran

6-O-acetyl-2,3,4,-tri-O-benzyl-α-D-glucopyranose

Downstream raw materials:

Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-[(2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-pyran-2-yloxy]-ethyl ester

Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-((2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-ethyl ester

Hexadecanoic acid (S)-1-hexadecanoyloxymethyl-2-{(2S,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-[(2-bromo-ethoxy)-hydroxy-phosphoryloxymethyl]-tetrahydro-pyran-2-yloxy}-ethyl ester

C₆₇H₁₀₈NO₁₃P