(3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)oxy]heptadecanoate

Base Information

• Chemical Name: (3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)oxy]heptadecanoate
• CAS No.: 704910-56-5
• Molecular Formula: C₇₁H₉₄O₉Si
• Molecular Weight: 1119.61
• Mol file: 704910-56-5.mol

Synonyms:(3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)oxy]heptadecanoate

Chemical Property of (3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)oxy]heptadecanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)oxy]heptadecanoate

There total 1 articles about (3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)oxy]heptadecanoate 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: 91.0%

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (74808-09-6) + 17-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-heptadecanoic acid tert-butyl ester (404867-96-5) → (3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)oxy]heptadecanoate (704910-56-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; acetonitrile; at -50 ℃; for 0.5h;

DOI:10.1002/chem.200305588

Reference yield: 90.0%

(3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)oxy]heptadecanoate (704910-56-5) → (3R)-tert-butyl [3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)oxy]heptadecanoate (704910-65-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1002/chem.200305588

Reference yield:

(3R)-tert-butyl [17-tert-butyldiphenylsilyloxy-3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)oxy]heptadecanoate (704910-56-5) → (R)-17-Oxo-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid tert-butyl ester (704910-66-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 2 h / 20 °C

2: PCC / CH₂Cl₂ / 1.5 h / 20 °C

With tetrabutyl ammonium fluoride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane;

DOI:10.1002/chem.200305588

upstream raw materials:

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

17-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-heptadecanoic acid tert-butyl ester

Downstream raw materials:

(3R)-tert-butyl [3-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)oxy]heptadecanoate

(R)-17-Oxo-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-heptadecanoic acid tert-butyl ester

(3R,17S,23R)-23-Benzyloxy-17-hydroxy-3-((2R,3R,4S,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetracosanoic acid tert-butyl ester