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

Base Information

Chemical Name:(R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-oxo-heptadecanoic acid tert-butyl ester
CAS No.:628316-36-9
Molecular Formula:C₅₀H₇₀O₁₀
Molecular Weight:831.1
Hs Code.:

Synonyms:(R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-oxo-heptadecanoic acid tert-butyl ester

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Chemical Property of (R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-oxo-heptadecanoic acid tert-butyl ester

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Technology Process of (R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-oxo-heptadecanoic acid tert-butyl ester

There total 9 articles about (R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-oxo-heptadecanoic acid tert-butyl 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: 98.0%

: 628316-35-8
(3R)-tert-butyl-[3-(6-O-acetyl-2,3,4-tri-O-benzyl-β-D-glucopyranosyl)oxy]heptadecanoate

: 628316-36-9
(R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-oxo-heptadecanoic acid tert-butyl ester

Guidance literature:: With pyridinium chlorochromate; In dichloromethane; at 20 ℃; for 1.5h;
DOI:10.1021/ja036521e

Reference yield:

: 125164-10-5
6-O-acetyl-2,3,4-tri-O-benzyl-α-D-glucopyranosyl trichloroacetimidate

: 628316-36-9
(R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-oxo-heptadecanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 74 percent / TMSOTf / CH₂Cl₂; acetonitrile / 0.5 h / -50 °C

2: 92 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 2 h / 20 °C

3: PCC / CH₂Cl₂ / 1.5 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1002/chem.200305588

Reference yield:

: 404867-96-5
17-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-heptadecanoic acid tert-butyl ester

: 628316-36-9
(R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-17-oxo-heptadecanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 74 percent / TMSOTf / CH₂Cl₂; acetonitrile / 0.5 h / -50 °C

2: 92 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 2 h / 20 °C

3: PCC / CH₂Cl₂ / 1.5 h / 20 °C

With trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; pyridinium chlorochromate; In tetrahydrofuran; dichloromethane; acetonitrile;
DOI:10.1002/chem.200305588