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

Base Information

Chemical Name:(3R,17S,23R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-23-benzyloxy-17-hydroxy-tetracosanoic acid tert-butyl ester
CAS No.:628316-38-1
Molecular Formula:C₆₄H₉₂O₁₁
Molecular Weight:1037.43
Hs Code.:

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

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

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

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

There total 15 articles about (3R,17S,23R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-23-benzyloxy-17-hydroxy-tetracosanoic 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:

: C₂₈H₄₂O₂Zn

: 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

: 628316-38-1
(3R,17S,23R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-23-benzyloxy-17-hydroxy-tetracosanoic acid tert-butyl ester

Guidance literature:: With titanium(IV) isopropylate; C,C,C-trifluoro-N-(2-trifluoromethanesulfonylaminocyclohexyl)methanesulfonamide; In toluene; at -50 - -20 ℃; for 1h;
DOI:10.1021/ja036521e

Reference yield:

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

: 628316-38-1
(3R,17S,23R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-23-benzyloxy-17-hydroxy-tetracosanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 74 percent / TMSOTf / CH₂Cl₂; acetonitrile / 0.5 h / -50 °C

2.1: 92 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 2 h / 20 °C

3.1: PCC / CH₂Cl₂ / 1.5 h / 20 °C

4.1: Et₂Zn; CuCN

4.2: 810 mg / (S,S)-(1,2-cyclohexanediamine)bistriflate; Ti(OiPr)4 / toluene / 1 h / -50 - -20 °C

With trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; diethylzinc; 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

: 628316-38-1
(3R,17S,23R)-3-((2R,3R,4S,5R,6R)-6-Acetoxymethyl-3,4,5-tris-benzyloxy-tetrahydro-pyran-2-yloxy)-23-benzyloxy-17-hydroxy-tetracosanoic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 74 percent / TMSOTf / CH₂Cl₂; acetonitrile / 0.5 h / -50 °C

2.1: 92 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 2 h / 20 °C

3.1: PCC / CH₂Cl₂ / 1.5 h / 20 °C

4.1: Et₂Zn; CuCN

4.2: 810 mg / (S,S)-(1,2-cyclohexanediamine)bistriflate; Ti(OiPr)4 / toluene / 1 h / -50 - -20 °C

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