[(25R)-26-(Acetyloxy)-3α-hydroxy-5α-cholestan-15α-yl]2-(acetylamino)-2-deoxy-β-D-glucopyranoside

Base Information

• Chemical Name: [(25R)-26-(Acetyloxy)-3α-hydroxy-5α-cholestan-15α-yl]2-(acetylamino)-2-deoxy-β-D-glucopyranoside
• CAS No.: 94359-66-7
• Molecular Formula: C₃₇H₆₃NO₉
• Molecular Weight: 665.909
• Mol file: 94359-66-7.mol

Synonyms:Acetic acid (2R,6R)-6-[(3R,5S,8R,9S,10S,13R,14S,15S,17R)-15-((2R,3R,4R,5S,6R)-3-acetylamino-4,5-dihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-3-hydroxy-10,13-dimethyl-hexadecahydro-cyclopenta[a]phenanthren-17-yl]-2-methyl-heptyl ester;

Chemical Property of [(25R)-26-(Acetyloxy)-3α-hydroxy-5α-cholestan-15α-yl]2-(acetylamino)-2-deoxy-β-D-glucopyranoside

Chemical Property:

• Vapor Pressure: 8.04E-29mmHg at 25°C
• Melting Point: 134 - 136 °C
• Boiling Point: 789.7°C at 760 mmHg
• Flash Point: 431.4°C
• PSA: 154.78000
• Density: 1.19g/cm³
• LogP: 4.34150

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(25R)-26-(Acetyloxy)-3α-hydroxy-5α-cholestan-15α-yl]2-(acetylamino)-2-deoxy-β-D-glucopyranoside

There total 16 articles about [(25R)-26-(Acetyloxy)-3α-hydroxy-5α-cholestan-15α-yl]2-(acetylamino)-2-deoxy-β-D-glucopyranoside 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: 96.0%

(25R)-15α-(2-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyloxy)-3α-hydroxy-5α-cholestan-26-yl acetate (872465-39-9) → pavoninin-4 (94359-66-7)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; at 20 ℃;

DOI:10.1021/jo051733a

Reference yield:

(25R)-5α-cholest-16-ene-3α,26-diol 3,26-dibenzoate (872465-33-3) → pavoninin-4 (94359-66-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 60 percent / chromium trioxide; 3,5-dimethylpyrazole / CH₂Cl₂ / 5 h / -20 °C

2: 98 percent / NaBH₄; cerium trichloride / tetrahydrofuran; methanol / 2 h / 20 °C

3: 98 percent / H₂ / Pd(OH)2/C / ethyl acetate / 3 h

4: 72 percent / AgClO₄; SnCl₂ / CH₂Cl₂ / 16 h / 0 °C

5: 90 percent / KOH / methanol; CH₂Cl₂ / 12 h / Heating

6: 80 percent / Bu₈Sn₄Cl₄O₂ / CH₂Cl₂ / 12 h / 20 °C

7: 96 percent / H₂ / Pd/C / methanol / 20 °C

With 3,5-dimethyl-1H-pyrazole; chromium(VI) oxide; potassium hydroxide; sodium tetrahydroborate; cerium(III) chloride; Bu₈Sn₄Cl₄O₂; hydrogen; silver perchlorate; tin(ll) chloride; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 2: Luche reduction / 6: Otera's transesterification;

DOI:10.1021/jo051733a

Reference yield:

(25R)-3α,26-dihydroxy-5α-cholest-16-en-15-one 3,26-dibenzoate (872465-34-4) → pavoninin-4 (94359-66-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 98 percent / NaBH₄; cerium trichloride / tetrahydrofuran; methanol / 2 h / 20 °C

2: 98 percent / H₂ / Pd(OH)2/C / ethyl acetate / 3 h

3: 72 percent / AgClO₄; SnCl₂ / CH₂Cl₂ / 16 h / 0 °C

4: 90 percent / KOH / methanol; CH₂Cl₂ / 12 h / Heating

5: 80 percent / Bu₈Sn₄Cl₄O₂ / CH₂Cl₂ / 12 h / 20 °C

6: 96 percent / H₂ / Pd/C / methanol / 20 °C

With potassium hydroxide; sodium tetrahydroborate; cerium(III) chloride; Bu₈Sn₄Cl₄O₂; hydrogen; silver perchlorate; tin(ll) chloride; palladium dihydroxide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; 1: Luche reduction / 5: Otera's transesterification;

DOI:10.1021/jo051733a

upstream raw materials:

(25R)-15α-(2-acetylamino-3,4,6-tri-O-benzyl-2-deoxy-β-D-glucopyranosyloxy)-3α-hydroxy-5α-cholestan-26-yl acetate

(25R)-5α-cholest-16-ene-3α,26-diol 3,26-dibenzoate

(25R)-3α,26-dihydroxy-5α-cholest-16-en-15-one 3,26-dibenzoate

(25R)-5α-cholestane-3α,15α,26-triol 3,26-dibenzoate

Refernces

• 1、 Tachibana, Kazuo,Sakaitani, Masahiro,Nakanishi, Koji. "PAVONININS, SHARK-REPELLING AND ICHTHYOTOXIC STEROID N-ACETYLGLUCOSAMINIDES FROM THE DEFENSE SECRETION OF THE SOLE PARDACHIRUS PAVONINUS (SOLEIDAE)". . p. 1027 - 1038. Retrieved 2007/10/02.