(1S,3S,5S,6R,7S,7aS)-6,7-dibenzoyloxy-3-di(ethoxycarbonyl)methyl-5-ethylthio-1-(p-methoxybenzyl)oxymethyl-2-oxapyrrolizidine

Base Information

• Chemical Name: (1S,3S,5S,6R,7S,7aS)-6,7-dibenzoyloxy-3-di(ethoxycarbonyl)methyl-5-ethylthio-1-(p-methoxybenzyl)oxymethyl-2-oxapyrrolizidine
• CAS No.: 610314-52-8
• Molecular Formula: C₃₈H₄₃NO₁₁S
• Molecular Weight: 721.826
• Mol file: 610314-52-8.mol

Synonyms:(1S,3S,5S,6R,7S,7aS)-6,7-dibenzoyloxy-3-di(ethoxycarbonyl)methyl-5-ethylthio-1-(p-methoxybenzyl)oxymethyl-2-oxapyrrolizidine

Chemical Property of (1S,3S,5S,6R,7S,7aS)-6,7-dibenzoyloxy-3-di(ethoxycarbonyl)methyl-5-ethylthio-1-(p-methoxybenzyl)oxymethyl-2-oxapyrrolizidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,5S,6R,7S,7aS)-6,7-dibenzoyloxy-3-di(ethoxycarbonyl)methyl-5-ethylthio-1-(p-methoxybenzyl)oxymethyl-2-oxapyrrolizidine

There total 7 articles about (1S,3S,5S,6R,7S,7aS)-6,7-dibenzoyloxy-3-di(ethoxycarbonyl)methyl-5-ethylthio-1-(p-methoxybenzyl)oxymethyl-2-oxapyrrolizidine 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:

ethanethiol (75-08-1) + 1,4-anhydro-2,3-di-O-benzoyl-N-(2,2-di(ethoxycarbonyl)vinyl)-6-O-(4-methoxybenzyl)-β-D-glucopyranosylamine (610314-51-7) → (1S,3S,5R,6R,7S,7aS)-6,7-dibenzoyloxy-3-di(ethoxycarbonyl)methyl-5-ethylthio-1-(p-methoxybenzyl)oxymethyl-2-oxapyrrolizidine + (1S,3S,5S,6R,7S,7aS)-6,7-dibenzoyloxy-3-di(ethoxycarbonyl)methyl-5-ethylthio-1-(p-methoxybenzyl)oxymethyl-2-oxapyrrolizidine (610314-52-8)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; at 20 ℃; for 0.0833333h;

DOI:10.1016/S0040-4039(03)01685-X

Reference yield:

N-(2,2-diethoxycarbonylvinyl)-β-D-glucopyranosylamine (22435-63-8) → (1S,3S,5S,6R,7S,7aS)-6,7-dibenzoyloxy-3-di(ethoxycarbonyl)methyl-5-ethylthio-1-(p-methoxybenzyl)oxymethyl-2-oxapyrrolizidine (610314-52-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / PTSA / dimethylformamide / 25 h / 50 °C / 20 Torr

2: 91 percent / pyridine / 24 h / 20 °C

3: 68 percent / sodium cyanoborohydride; acetic acid / 2.5 h / 20 °C

4: 85 percent / pyridine / 24 h / 20 °C

5: 66 percent / sodium methoxide / dimethylformamide / 0.25 h / 40 °C / 20 Torr

6: molecular sieves 3 Angstroem; p-toluenesulfonic acid / CH₂Cl₂ / 0.25 h / 20 °C

With pyridine; 3 A molecular sieve; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2004.01.003

Reference yield:

p-Anisaldehyde dimethyl acetal (2186-92-7) → (1S,3S,5S,6R,7S,7aS)-6,7-dibenzoyloxy-3-di(ethoxycarbonyl)methyl-5-ethylthio-1-(p-methoxybenzyl)oxymethyl-2-oxapyrrolizidine (610314-52-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / PTSA / dimethylformamide / 25 h / 50 °C / 20 Torr

2: 91 percent / pyridine / 24 h / 20 °C

3: 68 percent / sodium cyanoborohydride; acetic acid / 2.5 h / 20 °C

4: 85 percent / pyridine / 24 h / 20 °C

5: 66 percent / sodium methoxide / dimethylformamide / 0.25 h / 40 °C / 20 Torr

6: molecular sieves 3 Angstroem; p-toluenesulfonic acid / CH₂Cl₂ / 0.25 h / 20 °C

With pyridine; 3 A molecular sieve; sodium methylate; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.tetasy.2004.01.003

upstream raw materials:

ethanethiol

1,4-anhydro-2,3-di-O-benzoyl-N-(2,2-di(ethoxycarbonyl)vinyl)-6-O-(4-methoxybenzyl)-β-D-glucopyranosylamine

N-(2,2-diethoxycarbonylvinyl)-β-D-glucopyranosylamine

p-Anisaldehyde dimethyl acetal