3-<(tri-O-benzoyl-α-L-rhamnopyranosyl)oxy>-17β-(hydroxymethyl)-5β-androstane-3β,14β-diol

Base Information

• Chemical Name: 3-<(tri-O-benzoyl-α-L-rhamnopyranosyl)oxy>-17β-(hydroxymethyl)-5β-androstane-3β,14β-diol
• CAS No.: 188976-60-5
• Molecular Formula: C₄₇H₅₆O₁₀
• Molecular Weight: 780.956
• Mol file: 188976-60-5.mol

Synonyms:3-<(tri-O-benzoyl-α-L-rhamnopyranosyl)oxy>-17β-(hydroxymethyl)-5β-androstane-3β,14β-diol

Chemical Property of 3-<(tri-O-benzoyl-α-L-rhamnopyranosyl)oxy>-17β-(hydroxymethyl)-5β-androstane-3β,14β-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-<(tri-O-benzoyl-α-L-rhamnopyranosyl)oxy>-17β-(hydroxymethyl)-5β-androstane-3β,14β-diol

There total 5 articles about 3-<(tri-O-benzoyl-α-L-rhamnopyranosyl)oxy>-17β-(hydroxymethyl)-5β-androstane-3β,14β-diol 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: 57.0%

14-hydroxy-3β-<(tri-O-benzoyl-α-L-rhamnopyranosyl)oxy>-21-nor-5β,14β-pregnane-20-carboxaldehyde (145345-70-6) → 3-<(tri-O-benzoyl-α-L-rhamnopyranosyl)oxy>-17β-(hydroxymethyl)-5β-androstane-3β,14β-diol (188976-60-5)

Guidance literature:

With lithium tri(t-butoxy)aluminum hydride; In diethyl ether;

DOI:10.1021/jm960880l

Reference yield:

evomonoside α-L-rhamnopyranoside tribenzoate (144879-84-5) → 3-<(tri-O-benzoyl-α-L-rhamnopyranosyl)oxy>-17β-(hydroxymethyl)-5β-androstane-3β,14β-diol (188976-60-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) O₃, 2.) Zn / 1.) CH₂Cl₂, -70 deg C, 1 h, 2.) CH₂Cl₂, from -70 deg C to RT, 2 h

2: aq. KHCO₃ / methanol / 14 h

3: lithium tri-tert-butoxyaluminum hydride / diethyl ether / 1 h

4: aq. NaIO₄ / ethanol / 1 h

5: lithium tri-tert-butoxyaluminum hydride / diethyl ether / 1 h

With sodium periodate; lithium tri(t-butoxy)aluminum hydride; potassium hydrogencarbonate; ozone; zinc; In methanol; diethyl ether; ethanol;

DOI:10.1021/jm00053a006

Reference yield:

C48H58O11 → 3-<(tri-O-benzoyl-α-L-rhamnopyranosyl)oxy>-17β-(hydroxymethyl)-5β-androstane-3β,14β-diol (188976-60-5)

Guidance literature:

Multi-step reaction with 2 steps

1: aq. NaIO₄ / ethanol / 1 h

2: lithium tri-tert-butoxyaluminum hydride / diethyl ether / 1 h

With sodium periodate; lithium tri(t-butoxy)aluminum hydride; In diethyl ether; ethanol;

DOI:10.1021/jm00053a006

upstream raw materials:

14-hydroxy-3β-<(tri-O-benzoyl-α-L-rhamnopyranosyl)oxy>-21-nor-5β,14β-pregnane-20-carboxaldehyde

evomonoside α-L-rhamnopyranoside tribenzoate

Downstream raw materials:

3β-[(tri-O-benzoyl-α-L-rhamnopyranosyl)oxy]-17β-methylene-5β-androstane 14β,20-epoxide