6β-methoxy-16β,17α-dihydroxy-3α,5-cyclo-26,27-dinor-5α-cholestan-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl]-(1->3)-2-O-acetyl-4-O-triethylsilyl-β-L-arabinopyranoside}

Base Information

• Chemical Name: 6β-methoxy-16β,17α-dihydroxy-3α,5-cyclo-26,27-dinor-5α-cholestan-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl]-(1->3)-2-O-acetyl-4-O-triethylsilyl-β-L-arabinopyranoside}
• CAS No.: 721959-03-1
• Molecular Formula: C₆₄H₁₀₈O₁₅Si₃
• Molecular Weight: 1201.81
• Mol file: 721959-03-1.mol

Synonyms:6β-methoxy-16β,17α-dihydroxy-3α,5-cyclo-26,27-dinor-5α-cholestan-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl]-(1->3)-2-O-acetyl-4-O-triethylsilyl-β-L-arabinopyranoside}

Chemical Property of 6β-methoxy-16β,17α-dihydroxy-3α,5-cyclo-26,27-dinor-5α-cholestan-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl]-(1->3)-2-O-acetyl-4-O-triethylsilyl-β-L-arabinopyranoside}

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6β-methoxy-16β,17α-dihydroxy-3α,5-cyclo-26,27-dinor-5α-cholestan-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl]-(1->3)-2-O-acetyl-4-O-triethylsilyl-β-L-arabinopyranoside}

There total 3 articles about 6β-methoxy-16β,17α-dihydroxy-3α,5-cyclo-26,27-dinor-5α-cholestan-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl]-(1->3)-2-O-acetyl-4-O-triethylsilyl-β-L-arabinopyranoside} 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: 2.0%

2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1->3)-2'-O-acetyl-4'-O-triethylsilyl-α-L-arabinopyranosyl trichloroacetimidate + 6β-methoxy-3α,5-cyclo-26,27-dinor-5α-furostane-17α,22α-diol (721958-89-0) → 6β-methoxy-16β,17α-dihydroxy-3α,5-cyclo-26,27-dinor-5α-cholestan-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl]-(1->3)-2-O-acetyl-4-O-triethylsilyl-β-L-arabinopyranoside} (721959-03-1)

Guidance literature:

2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1->3)-2'-O-acetyl-4'-O-triethylsilyl-α-L-arabinopyranosyl trichloroacetimidate; 6β-methoxy-3α,5-cyclo-26,27-dinor-5α-furostane-17α,22α-diol; With 4 A molecular sieve; In dichloromethane; at 20 ℃; for 0.25h;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -68 ℃; for 0.5h; Further stages.;

DOI:10.1021/jm0613572

Reference yield:

(20S)-6β-methoxy-17α-hydroxy-3α,5α-cyclopregnane-20,16β-carbolactone (285979-64-8) → 6β-methoxy-16β,17α-dihydroxy-3α,5-cyclo-26,27-dinor-5α-cholestan-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl]-(1->3)-2-O-acetyl-4-O-triethylsilyl-β-L-arabinopyranoside} (721959-03-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: lithium / diethyl ether

1.2: 73 percent / diethyl ether / 2 h / 20 °C

2.1: molecular sieves 4 Angstroem / CH₂Cl₂ / 0.25 h / 20 °C

2.2: 2 percent / TMSOTf / CH₂Cl₂ / 0.5 h / -68 °C

With 4 A molecular sieve; lithium; In diethyl ether; dichloromethane;

DOI:10.1021/jm0613572

Reference yield:

2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1→3)-2-O-acetyl-4-O-triethylsilyl-α,β-L-arabinopyranosyl trichloroacetimidate (321125-08-0) + 6β-methoxy-3α,5-cyclo-26,27-dinor-5α-furostane-17α,22α-diol (721958-89-0) → 6β-methoxy-16β,17α-dihydroxy-3α,5-cyclo-26,27-dinor-5α-cholestan-22-one 16-O-{O-[2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl]-(1->3)-2-O-acetyl-4-O-triethylsilyl-β-L-arabinopyranoside} (721959-03-1)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate;

DOI:10.1016/j.bmcl.2004.03.102

upstream raw materials:

2-O-(4-methoxybenzoyl)-3,4-di-O-triethylsilyl-β-D-xylopyranosyl-(1→3)-2-O-acetyl-4-O-triethylsilyl-α,β-L-arabinopyranosyl trichloroacetimidate

6β-methoxy-3α,5-cyclo-26,27-dinor-5α-furostane-17α,22α-diol

(20S)-6β-methoxy-17α-hydroxy-3α,5α-cyclopregnane-20,16β-carbolactone