(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

Base Information

• Chemical Name: (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
• CAS No.: 704910-67-8
• Molecular Formula: C₆₉H₉₆O₁₀
• Molecular Weight: 1085.52
• Mol file: 704910-67-8.mol

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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

There total 9 articles about (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 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:

(6R)-6-O-benzyl-1-iodo-6-heptanol (465519-03-3) + (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) → (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 (704910-67-8)

Guidance literature:

(6R)-6-O-benzyl-1-iodo-6-heptanol; With diethylzinc;

(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; With titanium(IV) isopropylate; (S,S)-(1,2-cyclohexanediamine)bistriflate; In toluene; at -50 - -20 ℃; for 1h;

DOI:10.1002/chem.200305588

Reference yield:

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl trichloroacetimidate (74808-09-6) → (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 (704910-67-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 91 percent / TMSOTf / CH₂Cl₂; acetonitrile / 0.5 h / -50 °C

2.1: 90 percent / tetrabutylammonium fluoride trihydrate / tetrahydrofuran / 2 h / 20 °C

3.1: PCC / CH₂Cl₂ / 1.5 h / 20 °C

4.1: Et₂Zn; CuCN

4.2: 350 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:

benzyl bromide (100-39-0) → (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 (704910-67-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 73 percent / NaH

2.1: 93 percent / TBAF / tetrahydrofuran

3.1: 89 percent / I₂; PPh₃; imidazole

4.1: Et₂Zn; CuCN

4.2: 350 mg / (S,S)-(1,2-cyclohexanediamine)bistriflate; Ti(OiPr)4 / toluene / 1 h / -50 - -20 °C

With 1H-imidazole; tetrabutyl ammonium fluoride; iodine; diethylzinc; sodium hydride; triphenylphosphine; In tetrahydrofuran;

DOI:10.1002/chem.200305588

upstream raw materials:

(6R)-6-O-benzyl-1-iodo-6-heptanol

(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

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

benzyl bromide